<?xml version="1.0" encoding="UTF-8"?>

<!--XBRL Document Created with the Workiva Platform-->
<!--Copyright 2023 Workiva-->
<!--r:60a6bac0-0825-44a3-bd64-b991283925cc,g:6ea08b18-524f-4cb0-aa71-722b1aa2f0d9-->
<link:linkbase xmlns:link="http://www.xbrl.org/2003/linkbase" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xmlns:xbrldt="http://xbrl.org/2005/xbrldt" xsi:schemaLocation="http://www.xbrl.org/2003/linkbase http://www.xbrl.org/2003/xbrl-linkbase-2003-12-31.xsd">
  <link:arcroleRef arcroleURI="http://xbrl.org/int/dim/arcrole/all" xlink:type="simple" xlink:href="http://www.xbrl.org/2005/xbrldt-2005.xsd#all"/>
  <link:arcroleRef arcroleURI="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:type="simple" xlink:href="http://www.xbrl.org/2005/xbrldt-2005.xsd#hypercube-dimension"/>
  <link:arcroleRef arcroleURI="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:type="simple" xlink:href="http://www.xbrl.org/2005/xbrldt-2005.xsd#dimension-default"/>
  <link:arcroleRef arcroleURI="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:type="simple" xlink:href="http://www.xbrl.org/2005/xbrldt-2005.xsd#dimension-domain"/>
  <link:arcroleRef arcroleURI="http://xbrl.org/int/dim/arcrole/domain-member" xlink:type="simple" xlink:href="http://www.xbrl.org/2005/xbrldt-2005.xsd#domain-member"/>
  <link:roleRef roleURI="http://www.overstock.com/role/ConsolidatedStatementsofChangesinStockholdersEquityUnaudited" xlink:type="simple" xlink:href="ostk-20230630.xsd#ConsolidatedStatementsofChangesinStockholdersEquityUnaudited"/>
  <link:definitionLink xlink:role="http://www.overstock.com/role/ConsolidatedStatementsofChangesinStockholdersEquityUnaudited" xlink:type="extended" id="i882099e94faf41368dbf291966ee08a9_ConsolidatedStatementsofChangesinStockholdersEquityUnaudited">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementLineItems_241e94e9-ba3a-433a-b7cc-5811c1aedfda" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_StatementLineItems"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IncreaseDecreaseInStockholdersEquityRollForward"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_StatementLineItems_241e94e9-ba3a-433a-b7cc-5811c1aedfda" xlink:to="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockSharesOutstanding_63d78195-11bb-4c3c-a659-9661ff4a79c1" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_CommonStockSharesOutstanding"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:to="loc_us-gaap_CommonStockSharesOutstanding_63d78195-11bb-4c3c-a659-9661ff4a79c1" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SharesOutstanding_f4221c2a-cefb-4ec2-b587-da5e08ece481" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_SharesOutstanding"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:to="loc_us-gaap_SharesOutstanding_f4221c2a-cefb-4ec2-b587-da5e08ece481" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockIssuedDuringPeriodSharesRestrictedStockAwardNetOfForfeitures_48e0063a-797b-47f0-b6c4-66d8eadc55a8" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_StockIssuedDuringPeriodSharesRestrictedStockAwardNetOfForfeitures"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:to="loc_us-gaap_StockIssuedDuringPeriodSharesRestrictedStockAwardNetOfForfeitures_48e0063a-797b-47f0-b6c4-66d8eadc55a8" xlink:type="arc" order="3"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockIssuedDuringPeriodSharesEmployeeStockPurchasePlans_bd5d4525-2724-4405-9bc7-46e7253d854e" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_StockIssuedDuringPeriodSharesEmployeeStockPurchasePlans"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:to="loc_us-gaap_StockIssuedDuringPeriodSharesEmployeeStockPurchasePlans_bd5d4525-2724-4405-9bc7-46e7253d854e" xlink:type="arc" order="4"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockValueOutstanding_43369a02-73dc-4fb8-bb2c-64bf8a8e2237" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_CommonStockValueOutstanding"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:to="loc_us-gaap_CommonStockValueOutstanding_43369a02-73dc-4fb8-bb2c-64bf8a8e2237" xlink:type="arc" order="5"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockPreferredShares_2a802f05-348e-46eb-b333-63c25459f1f3" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_TreasuryStockPreferredShares"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:to="loc_us-gaap_TreasuryStockPreferredShares_2a802f05-348e-46eb-b333-63c25459f1f3" xlink:type="arc" order="6"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockSharesIssued_8404ef5f-4172-4c1f-9ed0-395ea610fbe2" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PreferredStockSharesIssued"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:to="loc_us-gaap_PreferredStockSharesIssued_8404ef5f-4172-4c1f-9ed0-395ea610fbe2" xlink:type="arc" order="7"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockSharesAcquired_786b0439-f324-4409-87cb-8c2416dc3620" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_TreasuryStockSharesAcquired"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:to="loc_us-gaap_TreasuryStockSharesAcquired_786b0439-f324-4409-87cb-8c2416dc3620" xlink:type="arc" order="8"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockPreferredShares_db1197b7-2b61-4761-81b7-aa098f95e1f1" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_TreasuryStockPreferredShares"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockSharesRetired_4f5ed16d-abdd-4f02-94b3-2035ea7aeb67" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_TreasuryStockSharesRetired"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:to="loc_us-gaap_TreasuryStockSharesRetired_4f5ed16d-abdd-4f02-94b3-2035ea7aeb67" xlink:type="arc" order="10"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockSharesOutstanding_b1abb019-7272-4071-a4ef-7e6e7abc9ec2" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PreferredStockSharesOutstanding"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:to="loc_us-gaap_PreferredStockSharesOutstanding_b1abb019-7272-4071-a4ef-7e6e7abc9ec2" xlink:type="arc" order="11"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockValue_b2eabf68-4fc0-407a-9bcf-1c46dc9cee37" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PreferredStockValue"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:to="loc_us-gaap_PreferredStockValue_b2eabf68-4fc0-407a-9bcf-1c46dc9cee37" xlink:type="arc" order="12"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquity_e45208da-feb1-4858-b0e6-03aeeff1efc1" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_StockholdersEquity"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:to="loc_us-gaap_StockholdersEquity_e45208da-feb1-4858-b0e6-03aeeff1efc1" xlink:type="arc" order="13"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdjustmentsToAdditionalPaidInCapitalShareBasedCompensationEmployeeStockPurchaseProgramRequisiteServicePeriodRecognition_1401eb29-6bdb-4c27-8672-1d1bc546d006" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AdjustmentsToAdditionalPaidInCapitalShareBasedCompensationEmployeeStockPurchaseProgramRequisiteServicePeriodRecognition"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:to="loc_us-gaap_AdjustmentsToAdditionalPaidInCapitalShareBasedCompensationEmployeeStockPurchaseProgramRequisiteServicePeriodRecognition_1401eb29-6bdb-4c27-8672-1d1bc546d006" xlink:type="arc" order="14"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss_6c4be754-5439-4414-8d32-0ee3ea163624" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_NetIncomeLoss"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:to="loc_us-gaap_NetIncomeLoss_6c4be754-5439-4414-8d32-0ee3ea163624" xlink:type="arc" order="15"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SharesPaidForTaxWithholdingForShareBasedCompensation_e4c3e7ac-d37e-4b00-b7a8-1f2bd4453b91" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_SharesPaidForTaxWithholdingForShareBasedCompensation"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:to="loc_us-gaap_SharesPaidForTaxWithholdingForShareBasedCompensation_e4c3e7ac-d37e-4b00-b7a8-1f2bd4453b91" xlink:type="arc" order="16"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdjustmentsRelatedToTaxWithholdingForShareBasedCompensation_40b8075b-42be-4a5a-8433-41f0a159802d" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AdjustmentsRelatedToTaxWithholdingForShareBasedCompensation"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:to="loc_us-gaap_AdjustmentsRelatedToTaxWithholdingForShareBasedCompensation_40b8075b-42be-4a5a-8433-41f0a159802d" xlink:type="arc" order="17"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockRetiredCostMethodAmount_783ab1b9-0cc9-42e8-b01c-18f37f75b14e" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_TreasuryStockRetiredCostMethodAmount"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:to="loc_us-gaap_TreasuryStockRetiredCostMethodAmount_783ab1b9-0cc9-42e8-b01c-18f37f75b14e" xlink:type="arc" order="18"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationRequisiteServicePeriodRecognitionValue_538a1e8d-a6c1-414e-b9f6-8746bbdf077e" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationRequisiteServicePeriodRecognitionValue"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:to="loc_us-gaap_AdjustmentsToAdditionalPaidInCapitalSharebasedCompensationRequisiteServicePeriodRecognitionValue_538a1e8d-a6c1-414e-b9f6-8746bbdf077e" xlink:type="arc" order="19"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_ConversionAndEliminationOfPreferredStock_b2532a5e-2021-4179-8036-11d03386e714" xlink:href="ostk-20230630.xsd#ostk_ConversionAndEliminationOfPreferredStock"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:to="loc_ostk_ConversionAndEliminationOfPreferredStock_b2532a5e-2021-4179-8036-11d03386e714" xlink:type="arc" order="20"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdjustmentsToAdditionalPaidInCapitalOther_39eb01fc-5ee8-4c55-b8e5-9c790fe842a1" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AdjustmentsToAdditionalPaidInCapitalOther"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:to="loc_us-gaap_AdjustmentsToAdditionalPaidInCapitalOther_39eb01fc-5ee8-4c55-b8e5-9c790fe842a1" xlink:type="arc" order="21"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockValueAcquiredCostMethod_f1a5d8fa-acd2-43d9-92c0-b69beb77120e" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_TreasuryStockValueAcquiredCostMethod"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:to="loc_us-gaap_TreasuryStockValueAcquiredCostMethod_f1a5d8fa-acd2-43d9-92c0-b69beb77120e" xlink:type="arc" order="22"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockConversionsInducements_ad6bce70-d5b1-443d-a09d-cb411df6d21a" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PreferredStockConversionsInducements"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:to="loc_us-gaap_PreferredStockConversionsInducements_ad6bce70-d5b1-443d-a09d-cb411df6d21a" xlink:type="arc" order="23"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockIssuedDuringPeriodValueConversionOfConvertibleSecurities_a91c6e6a-8f89-4f3f-b254-81a7dd644e82" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_StockIssuedDuringPeriodValueConversionOfConvertibleSecurities"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:to="loc_us-gaap_StockIssuedDuringPeriodValueConversionOfConvertibleSecurities_a91c6e6a-8f89-4f3f-b254-81a7dd644e82" xlink:type="arc" order="24"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTax_9974d8ce-534e-4777-98f1-93231413ecbb" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_OtherComprehensiveIncomeLossNetOfTax"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ef4326f0-31b6-421b-8388-e5acf60082af" xlink:to="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTax_9974d8ce-534e-4777-98f1-93231413ecbb" xlink:type="arc" order="25"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_StockIssuedDuringPeriodSharesConversionOfPreferredStock_bf5de7e1-445f-4f45-8317-a98511a915d8" xlink:href="ostk-20230630.xsd#ostk_StockIssuedDuringPeriodSharesConversionOfPreferredStock"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_StatementLineItems_241e94e9-ba3a-433a-b7cc-5811c1aedfda" xlink:to="loc_ostk_StockIssuedDuringPeriodSharesConversionOfPreferredStock_bf5de7e1-445f-4f45-8317-a98511a915d8" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_StockIssuedDuringPeriodValueConversionOfPreferredStock_22d5ee98-554b-4e8f-a735-9cf82957553e" xlink:href="ostk-20230630.xsd#ostk_StockIssuedDuringPeriodValueConversionOfPreferredStock"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_StatementLineItems_241e94e9-ba3a-433a-b7cc-5811c1aedfda" xlink:to="loc_ostk_StockIssuedDuringPeriodValueConversionOfPreferredStock_22d5ee98-554b-4e8f-a735-9cf82957553e" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_PreferredStockSharesConverted_ac446893-9031-46b2-83e3-3184e7d5fa91" xlink:href="ostk-20230630.xsd#ostk_PreferredStockSharesConverted"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_StatementLineItems_241e94e9-ba3a-433a-b7cc-5811c1aedfda" xlink:to="loc_ostk_PreferredStockSharesConverted_ac446893-9031-46b2-83e3-3184e7d5fa91" xlink:type="arc" order="3"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementTable_1a0a4303-58d5-4b89-be8d-32061c3e6eec" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_StatementTable"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/all" xlink:from="loc_us-gaap_StatementLineItems_241e94e9-ba3a-433a-b7cc-5811c1aedfda" xlink:to="loc_us-gaap_StatementTable_1a0a4303-58d5-4b89-be8d-32061c3e6eec" xlink:type="arc" order="1" xbrldt:closed="true" xbrldt:contextElement="segment"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementClassOfStockAxis_459c58bd-82d1-4e5f-acee-bcae144a538c" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_StatementClassOfStockAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_StatementTable_1a0a4303-58d5-4b89-be8d-32061c3e6eec" xlink:to="loc_us-gaap_StatementClassOfStockAxis_459c58bd-82d1-4e5f-acee-bcae144a538c" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ClassOfStockDomain_459c58bd-82d1-4e5f-acee-bcae144a538c_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ClassOfStockDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_StatementClassOfStockAxis_459c58bd-82d1-4e5f-acee-bcae144a538c" xlink:to="loc_us-gaap_ClassOfStockDomain_459c58bd-82d1-4e5f-acee-bcae144a538c_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ClassOfStockDomain_9d87926e-6db4-4710-b9b3-aaef9593f36d" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ClassOfStockDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_StatementClassOfStockAxis_459c58bd-82d1-4e5f-acee-bcae144a538c" xlink:to="loc_us-gaap_ClassOfStockDomain_9d87926e-6db4-4710-b9b3-aaef9593f36d" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_SeriesA1PreferredStockMember_fe9c2e7b-2323-4a4d-ad2a-0b9c3245d3da" xlink:href="ostk-20230630.xsd#ostk_SeriesA1PreferredStockMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ClassOfStockDomain_9d87926e-6db4-4710-b9b3-aaef9593f36d" xlink:to="loc_ostk_SeriesA1PreferredStockMember_fe9c2e7b-2323-4a4d-ad2a-0b9c3245d3da" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SeriesBPreferredStockMember_c45e9194-b9e9-4160-ac17-bfa03128abf7" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_SeriesBPreferredStockMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ClassOfStockDomain_9d87926e-6db4-4710-b9b3-aaef9593f36d" xlink:to="loc_us-gaap_SeriesBPreferredStockMember_c45e9194-b9e9-4160-ac17-bfa03128abf7" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementEquityComponentsAxis_c9c657e1-9d89-4d9f-9197-adb3650a8546" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_StatementEquityComponentsAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_StatementTable_1a0a4303-58d5-4b89-be8d-32061c3e6eec" xlink:to="loc_us-gaap_StatementEquityComponentsAxis_c9c657e1-9d89-4d9f-9197-adb3650a8546" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityComponentDomain_c9c657e1-9d89-4d9f-9197-adb3650a8546_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EquityComponentDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_StatementEquityComponentsAxis_c9c657e1-9d89-4d9f-9197-adb3650a8546" xlink:to="loc_us-gaap_EquityComponentDomain_c9c657e1-9d89-4d9f-9197-adb3650a8546_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityComponentDomain_697edfbb-6526-4934-bbe3-53ea847c916a" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EquityComponentDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_StatementEquityComponentsAxis_c9c657e1-9d89-4d9f-9197-adb3650a8546" xlink:to="loc_us-gaap_EquityComponentDomain_697edfbb-6526-4934-bbe3-53ea847c916a" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockMember_36d46bec-1ed9-4de1-9081-d7eccc273bb8" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_CommonStockMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_EquityComponentDomain_697edfbb-6526-4934-bbe3-53ea847c916a" xlink:to="loc_us-gaap_CommonStockMember_36d46bec-1ed9-4de1-9081-d7eccc273bb8" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockMember_a8aedf91-8c11-48b5-b670-7433b326ba20" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PreferredStockMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_EquityComponentDomain_697edfbb-6526-4934-bbe3-53ea847c916a" xlink:to="loc_us-gaap_PreferredStockMember_a8aedf91-8c11-48b5-b670-7433b326ba20" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdditionalPaidInCapitalMember_885211ec-ad11-44f3-9081-7abf9f4b1861" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AdditionalPaidInCapitalMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_EquityComponentDomain_697edfbb-6526-4934-bbe3-53ea847c916a" xlink:to="loc_us-gaap_AdditionalPaidInCapitalMember_885211ec-ad11-44f3-9081-7abf9f4b1861" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RetainedEarningsMember_b1fe62b6-861c-4fd5-8eee-e0429a7c785a" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_RetainedEarningsMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_EquityComponentDomain_697edfbb-6526-4934-bbe3-53ea847c916a" xlink:to="loc_us-gaap_RetainedEarningsMember_b1fe62b6-861c-4fd5-8eee-e0429a7c785a" xlink:type="arc" order="3"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeMember_b6ba2c51-b1e3-4c77-bf9e-62e6066c64d8" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_EquityComponentDomain_697edfbb-6526-4934-bbe3-53ea847c916a" xlink:to="loc_us-gaap_AccumulatedOtherComprehensiveIncomeMember_b6ba2c51-b1e3-4c77-bf9e-62e6066c64d8" xlink:type="arc" order="4"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockCommonMember_404b7875-a8f6-479a-aae8-6650ca217481" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_TreasuryStockCommonMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_EquityComponentDomain_697edfbb-6526-4934-bbe3-53ea847c916a" xlink:to="loc_us-gaap_TreasuryStockCommonMember_404b7875-a8f6-479a-aae8-6650ca217481" xlink:type="arc" order="5"/>
  </link:definitionLink>
  <link:roleRef roleURI="http://www.overstock.com/role/SUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESNarrativeDetails" xlink:type="simple" xlink:href="ostk-20230630.xsd#SUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESNarrativeDetails"/>
  <link:definitionLink xlink:role="http://www.overstock.com/role/SUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESNarrativeDetails" xlink:type="extended" id="i5bd6389910b34cefafca39867f343639_SUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESNarrativeDetails">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentLineItems_11430fb0-febd-43db-92ec-603b0baf50bd" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtInstrumentLineItems"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentFaceAmount_9e419e2b-3616-4ac2-a3aa-95b25547b2d8" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtInstrumentFaceAmount"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_DebtInstrumentLineItems_11430fb0-febd-43db-92ec-603b0baf50bd" xlink:to="loc_us-gaap_DebtInstrumentFaceAmount_9e419e2b-3616-4ac2-a3aa-95b25547b2d8" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentInterestRateStatedPercentage_1df4a1e1-3c49-4cab-b4d7-15c471c3d37a" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtInstrumentInterestRateStatedPercentage"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_DebtInstrumentLineItems_11430fb0-febd-43db-92ec-603b0baf50bd" xlink:to="loc_us-gaap_DebtInstrumentInterestRateStatedPercentage_1df4a1e1-3c49-4cab-b4d7-15c471c3d37a" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentCarryingAmount_bf9ef4bd-87df-4455-b8be-280efd1b4f69" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtInstrumentCarryingAmount"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_DebtInstrumentLineItems_11430fb0-febd-43db-92ec-603b0baf50bd" xlink:to="loc_us-gaap_DebtInstrumentCarryingAmount_bf9ef4bd-87df-4455-b8be-280efd1b4f69" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableInterestEntityEntityMaximumLossExposureAmount_6f666798-ad36-44ea-9242-69cec58f7e6c" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_VariableInterestEntityEntityMaximumLossExposureAmount"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_DebtInstrumentLineItems_11430fb0-febd-43db-92ec-603b0baf50bd" xlink:to="loc_us-gaap_VariableInterestEntityEntityMaximumLossExposureAmount_6f666798-ad36-44ea-9242-69cec58f7e6c" xlink:type="arc" order="3"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentTable_025c615b-44cd-49a8-aba5-d7899b890596" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtInstrumentTable"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/all" xlink:from="loc_us-gaap_DebtInstrumentLineItems_11430fb0-febd-43db-92ec-603b0baf50bd" xlink:to="loc_us-gaap_DebtInstrumentTable_025c615b-44cd-49a8-aba5-d7899b890596" xlink:type="arc" order="1" xbrldt:closed="true" xbrldt:contextElement="segment"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentAxis_7984b0c1-32a7-4c1b-bd8c-edc8a9b24789" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtInstrumentAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_DebtInstrumentTable_025c615b-44cd-49a8-aba5-d7899b890596" xlink:to="loc_us-gaap_DebtInstrumentAxis_7984b0c1-32a7-4c1b-bd8c-edc8a9b24789" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentNameDomain_7984b0c1-32a7-4c1b-bd8c-edc8a9b24789_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtInstrumentNameDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_DebtInstrumentAxis_7984b0c1-32a7-4c1b-bd8c-edc8a9b24789" xlink:to="loc_us-gaap_DebtInstrumentNameDomain_7984b0c1-32a7-4c1b-bd8c-edc8a9b24789_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentNameDomain_cf7e7624-8e1d-44f4-95b2-ef6bfa880065" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtInstrumentNameDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_DebtInstrumentAxis_7984b0c1-32a7-4c1b-bd8c-edc8a9b24789" xlink:to="loc_us-gaap_DebtInstrumentNameDomain_cf7e7624-8e1d-44f4-95b2-ef6bfa880065" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_GrainChainIncConvertiblePromissoryNoteDue2025Member_34e2b0c5-5039-4160-b33e-eba65526d1b9" xlink:href="ostk-20230630.xsd#ostk_GrainChainIncConvertiblePromissoryNoteDue2025Member"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_DebtInstrumentNameDomain_cf7e7624-8e1d-44f4-95b2-ef6bfa880065" xlink:to="loc_ostk_GrainChainIncConvertiblePromissoryNoteDue2025Member_34e2b0c5-5039-4160-b33e-eba65526d1b9" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongtermDebtTypeAxis_6996b343-df1e-4c49-8c44-6a5c59b2a006" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LongtermDebtTypeAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_DebtInstrumentTable_025c615b-44cd-49a8-aba5-d7899b890596" xlink:to="loc_us-gaap_LongtermDebtTypeAxis_6996b343-df1e-4c49-8c44-6a5c59b2a006" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongtermDebtTypeDomain_6996b343-df1e-4c49-8c44-6a5c59b2a006_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LongtermDebtTypeDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_LongtermDebtTypeAxis_6996b343-df1e-4c49-8c44-6a5c59b2a006" xlink:to="loc_us-gaap_LongtermDebtTypeDomain_6996b343-df1e-4c49-8c44-6a5c59b2a006_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongtermDebtTypeDomain_3703028c-a491-47cd-b7b1-0f39e605ba0d" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LongtermDebtTypeDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_LongtermDebtTypeAxis_6996b343-df1e-4c49-8c44-6a5c59b2a006" xlink:to="loc_us-gaap_LongtermDebtTypeDomain_3703028c-a491-47cd-b7b1-0f39e605ba0d" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConvertibleDebtMember_95056999-3e71-40af-90b2-e789b116205e" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ConvertibleDebtMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_LongtermDebtTypeDomain_3703028c-a491-47cd-b7b1-0f39e605ba0d" xlink:to="loc_us-gaap_ConvertibleDebtMember_95056999-3e71-40af-90b2-e789b116205e" xlink:type="arc" order="0"/>
  </link:definitionLink>
  <link:roleRef roleURI="http://www.overstock.com/role/FAIRVALUEMEASUREMENTAssetsandLiabilitiesMeasuredAtFairValueDetails" xlink:type="simple" xlink:href="ostk-20230630.xsd#FAIRVALUEMEASUREMENTAssetsandLiabilitiesMeasuredAtFairValueDetails"/>
  <link:definitionLink xlink:role="http://www.overstock.com/role/FAIRVALUEMEASUREMENTAssetsandLiabilitiesMeasuredAtFairValueDetails" xlink:type="extended" id="i604f0d7f4df2434e95843dee20f5adbb_FAIRVALUEMEASUREMENTAssetsandLiabilitiesMeasuredAtFairValueDetails">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems_60d76113-28f6-4c2e-a26c-02a494c94bfb" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsFairValueDisclosureAbstract_d9c61dbd-f550-49dd-bd0b-7a0882326758" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AssetsFairValueDisclosureAbstract"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems_60d76113-28f6-4c2e-a26c-02a494c94bfb" xlink:to="loc_us-gaap_AssetsFairValueDisclosureAbstract_d9c61dbd-f550-49dd-bd0b-7a0882326758" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsFairValueDisclosure_4b1925ec-be3a-4362-8758-dd71a00895da" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_CashAndCashEquivalentsFairValueDisclosure"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_AssetsFairValueDisclosureAbstract_d9c61dbd-f550-49dd-bd0b-7a0882326758" xlink:to="loc_us-gaap_CashAndCashEquivalentsFairValueDisclosure_4b1925ec-be3a-4362-8758-dd71a00895da" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFVNINoncurrent_b500cafd-0e0c-45cb-be48-e323adfd5de0" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EquitySecuritiesFVNINoncurrent"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_AssetsFairValueDisclosureAbstract_d9c61dbd-f550-49dd-bd0b-7a0882326758" xlink:to="loc_us-gaap_EquitySecuritiesFVNINoncurrent_b500cafd-0e0c-45cb-be48-e323adfd5de0" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtSecurities_5301fbb4-0c75-4404-8b14-046f157a5c46" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AvailableForSaleSecuritiesDebtSecurities"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_AssetsFairValueDisclosureAbstract_d9c61dbd-f550-49dd-bd0b-7a0882326758" xlink:to="loc_us-gaap_AvailableForSaleSecuritiesDebtSecurities_5301fbb4-0c75-4404-8b14-046f157a5c46" xlink:type="arc" order="3"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TradingSecurities_0ce8741f-d0dd-4f7e-824c-cecf5cf08872" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_TradingSecurities"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_AssetsFairValueDisclosureAbstract_d9c61dbd-f550-49dd-bd0b-7a0882326758" xlink:to="loc_us-gaap_TradingSecurities_0ce8741f-d0dd-4f7e-824c-cecf5cf08872" xlink:type="arc" order="4"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsFairValueDisclosure_564f9f6b-5806-44af-b1d5-f92b93b639b8" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AssetsFairValueDisclosure"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_AssetsFairValueDisclosureAbstract_d9c61dbd-f550-49dd-bd0b-7a0882326758" xlink:to="loc_us-gaap_AssetsFairValueDisclosure_564f9f6b-5806-44af-b1d5-f92b93b639b8" xlink:type="arc" order="5"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesFairValueDisclosureAbstract_a1d9d3a6-5629-42b9-a05e-960cf14da99e" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LiabilitiesFairValueDisclosureAbstract"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems_60d76113-28f6-4c2e-a26c-02a494c94bfb" xlink:to="loc_us-gaap_LiabilitiesFairValueDisclosureAbstract_a1d9d3a6-5629-42b9-a05e-960cf14da99e" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredCompensationCashbasedArrangementsLiabilityCurrentAndNoncurrent_a5c79035-eb72-44ec-adf6-f6619681f10c" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DeferredCompensationCashbasedArrangementsLiabilityCurrentAndNoncurrent"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_LiabilitiesFairValueDisclosureAbstract_a1d9d3a6-5629-42b9-a05e-960cf14da99e" xlink:to="loc_us-gaap_DeferredCompensationCashbasedArrangementsLiabilityCurrentAndNoncurrent_a5c79035-eb72-44ec-adf6-f6619681f10c" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesFairValueDisclosure_2da7c89e-7649-487a-b5d9-3c5005bd839d" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LiabilitiesFairValueDisclosure"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_LiabilitiesFairValueDisclosureAbstract_a1d9d3a6-5629-42b9-a05e-960cf14da99e" xlink:to="loc_us-gaap_LiabilitiesFairValueDisclosure_2da7c89e-7649-487a-b5d9-3c5005bd839d" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable_7700ba2b-b203-4913-ba65-72f917149475" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/all" xlink:from="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems_60d76113-28f6-4c2e-a26c-02a494c94bfb" xlink:to="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable_7700ba2b-b203-4913-ba65-72f917149475" xlink:type="arc" order="1" xbrldt:closed="true" xbrldt:contextElement="segment"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByFairValueHierarchyLevelAxis_7d411423-884a-438e-98b5-8f8caa1b7c66" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueByFairValueHierarchyLevelAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable_7700ba2b-b203-4913-ba65-72f917149475" xlink:to="loc_us-gaap_FairValueByFairValueHierarchyLevelAxis_7d411423-884a-438e-98b5-8f8caa1b7c66" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_7d411423-884a-438e-98b5-8f8caa1b7c66_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueMeasurementsFairValueHierarchyDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_FairValueByFairValueHierarchyLevelAxis_7d411423-884a-438e-98b5-8f8caa1b7c66" xlink:to="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_7d411423-884a-438e-98b5-8f8caa1b7c66_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_514d37ab-b5a8-4056-b691-e9d31ccc7909" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueMeasurementsFairValueHierarchyDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_FairValueByFairValueHierarchyLevelAxis_7d411423-884a-438e-98b5-8f8caa1b7c66" xlink:to="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_514d37ab-b5a8-4056-b691-e9d31ccc7909" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel1Member_acd501ac-39a6-487c-9c1f-d5c5f2cad41f" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueInputsLevel1Member"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_514d37ab-b5a8-4056-b691-e9d31ccc7909" xlink:to="loc_us-gaap_FairValueInputsLevel1Member_acd501ac-39a6-487c-9c1f-d5c5f2cad41f" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel2Member_d247061e-3a19-410b-94b1-dc303253ff97" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueInputsLevel2Member"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_514d37ab-b5a8-4056-b691-e9d31ccc7909" xlink:to="loc_us-gaap_FairValueInputsLevel2Member_d247061e-3a19-410b-94b1-dc303253ff97" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel3Member_11b6ff40-6256-4e6e-9926-4f00975b1836" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueInputsLevel3Member"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_514d37ab-b5a8-4056-b691-e9d31ccc7909" xlink:to="loc_us-gaap_FairValueInputsLevel3Member_11b6ff40-6256-4e6e-9926-4f00975b1836" xlink:type="arc" order="2"/>
  </link:definitionLink>
  <link:roleRef roleURI="http://www.overstock.com/role/FAIRVALUEMEASUREMENTLevel3InvestmentActivityDetails" xlink:type="simple" xlink:href="ostk-20230630.xsd#FAIRVALUEMEASUREMENTLevel3InvestmentActivityDetails"/>
  <link:definitionLink xlink:role="http://www.overstock.com/role/FAIRVALUEMEASUREMENTLevel3InvestmentActivityDetails" xlink:type="extended" id="i262aea9479c5469291f84eedde28f4a2_FAIRVALUEMEASUREMENTLevel3InvestmentActivityDetails">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems_75ee86b0-c833-4f31-8919-58de863dc0b0" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward_c4b39493-0387-4193-a58d-b77405dc3c9c" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems_75ee86b0-c833-4f31-8919-58de863dc0b0" xlink:to="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward_c4b39493-0387-4193-a58d-b77405dc3c9c" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue_6abba65b-2d43-4d6d-a9ba-295fcc43d8ce" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward_c4b39493-0387-4193-a58d-b77405dc3c9c" xlink:to="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue_6abba65b-2d43-4d6d-a9ba-295fcc43d8ce" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases_02889690-48e3-4775-a148-aea37e114c80" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward_c4b39493-0387-4193-a58d-b77405dc3c9c" xlink:to="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases_02889690-48e3-4775-a148-aea37e114c80" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1_582cf270-21f9-45ca-bb68-610ca7e37302" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward_c4b39493-0387-4193-a58d-b77405dc3c9c" xlink:to="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1_582cf270-21f9-45ca-bb68-610ca7e37302" xlink:type="arc" order="3"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetAccruedInterest_fbe5246c-658d-4f6c-95ab-4513853e4f1d" xlink:href="ostk-20230630.xsd#ostk_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetAccruedInterest"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward_c4b39493-0387-4193-a58d-b77405dc3c9c" xlink:to="loc_ostk_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetAccruedInterest_fbe5246c-658d-4f6c-95ab-4513853e4f1d" xlink:type="arc" order="4"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable_b2efcc75-ae93-475f-a5ae-0ace8e29fc9e" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/all" xlink:from="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems_75ee86b0-c833-4f31-8919-58de863dc0b0" xlink:to="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable_b2efcc75-ae93-475f-a5ae-0ace8e29fc9e" xlink:type="arc" order="1" xbrldt:closed="true" xbrldt:contextElement="segment"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByFairValueHierarchyLevelAxis_16070c24-7f50-451c-b26c-af2ce1180aaf" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueByFairValueHierarchyLevelAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable_b2efcc75-ae93-475f-a5ae-0ace8e29fc9e" xlink:to="loc_us-gaap_FairValueByFairValueHierarchyLevelAxis_16070c24-7f50-451c-b26c-af2ce1180aaf" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_16070c24-7f50-451c-b26c-af2ce1180aaf_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueMeasurementsFairValueHierarchyDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_FairValueByFairValueHierarchyLevelAxis_16070c24-7f50-451c-b26c-af2ce1180aaf" xlink:to="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_16070c24-7f50-451c-b26c-af2ce1180aaf_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_59bcdb44-01c8-47f4-a22c-f518101c7ab9" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueMeasurementsFairValueHierarchyDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_FairValueByFairValueHierarchyLevelAxis_16070c24-7f50-451c-b26c-af2ce1180aaf" xlink:to="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_59bcdb44-01c8-47f4-a22c-f518101c7ab9" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel3Member_a85c9865-0f80-4757-9a9c-e663f3b68a97" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueInputsLevel3Member"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_59bcdb44-01c8-47f4-a22c-f518101c7ab9" xlink:to="loc_us-gaap_FairValueInputsLevel3Member_a85c9865-0f80-4757-9a9c-e663f3b68a97" xlink:type="arc" order="0"/>
  </link:definitionLink>
  <link:roleRef roleURI="http://www.overstock.com/role/PROPERTYANDEQUIPMENTNETDetails" xlink:type="simple" xlink:href="ostk-20230630.xsd#PROPERTYANDEQUIPMENTNETDetails"/>
  <link:definitionLink xlink:role="http://www.overstock.com/role/PROPERTYANDEQUIPMENTNETDetails" xlink:type="extended" id="i4e30326804e946c1abebc7dc652a2279_PROPERTYANDEQUIPMENTNETDetails">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentLineItems_1ae68dda-27d0-44c1-bbe8-851d9ad886b4" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PropertyPlantAndEquipmentLineItems"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentGross_32a67bf9-d949-4f11-ad4e-31f3a0dc89ef" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PropertyPlantAndEquipmentGross"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentLineItems_1ae68dda-27d0-44c1-bbe8-851d9ad886b4" xlink:to="loc_us-gaap_PropertyPlantAndEquipmentGross_32a67bf9-d949-4f11-ad4e-31f3a0dc89ef" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment_4a5fc79d-431f-4ca6-b577-de45b76b6995" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentLineItems_1ae68dda-27d0-44c1-bbe8-851d9ad886b4" xlink:to="loc_us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment_4a5fc79d-431f-4ca6-b577-de45b76b6995" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentNet_685642a3-08de-4c60-bf8a-800ea0ae29c4" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PropertyPlantAndEquipmentNet"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentLineItems_1ae68dda-27d0-44c1-bbe8-851d9ad886b4" xlink:to="loc_us-gaap_PropertyPlantAndEquipmentNet_685642a3-08de-4c60-bf8a-800ea0ae29c4" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfPropertyPlantAndEquipmentTable_068448a7-9c72-46f6-9bd8-1f42429c1116" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfPropertyPlantAndEquipmentTable"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/all" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentLineItems_1ae68dda-27d0-44c1-bbe8-851d9ad886b4" xlink:to="loc_us-gaap_ScheduleOfPropertyPlantAndEquipmentTable_068448a7-9c72-46f6-9bd8-1f42429c1116" xlink:type="arc" order="1" xbrldt:closed="true" xbrldt:contextElement="segment"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentByTypeAxis_4d01f3bf-842d-4714-8740-feb85af3fcb1" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PropertyPlantAndEquipmentByTypeAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_ScheduleOfPropertyPlantAndEquipmentTable_068448a7-9c72-46f6-9bd8-1f42429c1116" xlink:to="loc_us-gaap_PropertyPlantAndEquipmentByTypeAxis_4d01f3bf-842d-4714-8740-feb85af3fcb1" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentTypeDomain_4d01f3bf-842d-4714-8740-feb85af3fcb1_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PropertyPlantAndEquipmentTypeDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentByTypeAxis_4d01f3bf-842d-4714-8740-feb85af3fcb1" xlink:to="loc_us-gaap_PropertyPlantAndEquipmentTypeDomain_4d01f3bf-842d-4714-8740-feb85af3fcb1_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentTypeDomain_e1501f27-290b-4368-a90b-505788f58d77" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PropertyPlantAndEquipmentTypeDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentByTypeAxis_4d01f3bf-842d-4714-8740-feb85af3fcb1" xlink:to="loc_us-gaap_PropertyPlantAndEquipmentTypeDomain_e1501f27-290b-4368-a90b-505788f58d77" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_ComputerHardwareandSoftwareMember_d6c208fa-6e11-457a-ba77-2f76deb6871a" xlink:href="ostk-20230630.xsd#ostk_ComputerHardwareandSoftwareMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentTypeDomain_e1501f27-290b-4368-a90b-505788f58d77" xlink:to="loc_ostk_ComputerHardwareandSoftwareMember_d6c208fa-6e11-457a-ba77-2f76deb6871a" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BuildingMember_a80130f9-1517-417f-8a1b-3f19bbb8fb0d" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_BuildingMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentTypeDomain_e1501f27-290b-4368-a90b-505788f58d77" xlink:to="loc_us-gaap_BuildingMember_a80130f9-1517-417f-8a1b-3f19bbb8fb0d" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LandMember_1689fc41-1e27-447d-b301-9b389d7adeeb" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LandMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentTypeDomain_e1501f27-290b-4368-a90b-505788f58d77" xlink:to="loc_us-gaap_LandMember_1689fc41-1e27-447d-b301-9b389d7adeeb" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_FurnitureAndEquipmentMember_ae7debc1-b0ad-4206-bdcc-725bb584c6b8" xlink:href="ostk-20230630.xsd#ostk_FurnitureAndEquipmentMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentTypeDomain_e1501f27-290b-4368-a90b-505788f58d77" xlink:to="loc_ostk_FurnitureAndEquipmentMember_ae7debc1-b0ad-4206-bdcc-725bb584c6b8" xlink:type="arc" order="3"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MachineryAndEquipmentMember_19f59f3e-7249-4c9e-8ca6-64e0dd8ceaeb" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_MachineryAndEquipmentMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentTypeDomain_e1501f27-290b-4368-a90b-505788f58d77" xlink:to="loc_us-gaap_MachineryAndEquipmentMember_19f59f3e-7249-4c9e-8ca6-64e0dd8ceaeb" xlink:type="arc" order="4"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LandImprovementsMember_a760938b-3130-46b5-91fd-06f26b313ec1" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LandImprovementsMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentTypeDomain_e1501f27-290b-4368-a90b-505788f58d77" xlink:to="loc_us-gaap_LandImprovementsMember_a760938b-3130-46b5-91fd-06f26b313ec1" xlink:type="arc" order="5"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LeaseholdImprovementsMember_21faa5bc-3a48-4be7-be7d-0215bc9e5302" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LeaseholdImprovementsMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentTypeDomain_e1501f27-290b-4368-a90b-505788f58d77" xlink:to="loc_us-gaap_LeaseholdImprovementsMember_21faa5bc-3a48-4be7-be7d-0215bc9e5302" xlink:type="arc" order="6"/>
  </link:definitionLink>
  <link:roleRef roleURI="http://www.overstock.com/role/PROPERTYANDEQUIPMENTNETCapitalizedSoftwareWebsiteDevelopmentDetails" xlink:type="simple" xlink:href="ostk-20230630.xsd#PROPERTYANDEQUIPMENTNETCapitalizedSoftwareWebsiteDevelopmentDetails"/>
  <link:definitionLink xlink:role="http://www.overstock.com/role/PROPERTYANDEQUIPMENTNETCapitalizedSoftwareWebsiteDevelopmentDetails" xlink:type="extended" id="i3fe4bd69247a45349d09cb4667221925_PROPERTYANDEQUIPMENTNETCapitalizedSoftwareWebsiteDevelopmentDetails">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentLineItems_8801d29b-30a5-4b0c-a0e1-c8ed3cd105f8" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PropertyPlantAndEquipmentLineItems"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CapitalizedComputerSoftwareAdditions_c935ea39-8ff4-48a9-959e-d040be026ed7" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_CapitalizedComputerSoftwareAdditions"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentLineItems_8801d29b-30a5-4b0c-a0e1-c8ed3cd105f8" xlink:to="loc_us-gaap_CapitalizedComputerSoftwareAdditions_c935ea39-8ff4-48a9-959e-d040be026ed7" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CapitalizedComputerSoftwareAmortization1_7070b788-748a-4284-a91c-5d9a954110ed" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_CapitalizedComputerSoftwareAmortization1"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentLineItems_8801d29b-30a5-4b0c-a0e1-c8ed3cd105f8" xlink:to="loc_us-gaap_CapitalizedComputerSoftwareAmortization1_7070b788-748a-4284-a91c-5d9a954110ed" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfPropertyPlantAndEquipmentTable_b32c0129-b8c6-452d-81fd-d47260f0fd64" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfPropertyPlantAndEquipmentTable"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/all" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentLineItems_8801d29b-30a5-4b0c-a0e1-c8ed3cd105f8" xlink:to="loc_us-gaap_ScheduleOfPropertyPlantAndEquipmentTable_b32c0129-b8c6-452d-81fd-d47260f0fd64" xlink:type="arc" order="1" xbrldt:closed="true" xbrldt:contextElement="segment"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentByTypeAxis_f95f5cac-aefb-4097-8f2c-0a8652976706" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PropertyPlantAndEquipmentByTypeAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_ScheduleOfPropertyPlantAndEquipmentTable_b32c0129-b8c6-452d-81fd-d47260f0fd64" xlink:to="loc_us-gaap_PropertyPlantAndEquipmentByTypeAxis_f95f5cac-aefb-4097-8f2c-0a8652976706" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentTypeDomain_f95f5cac-aefb-4097-8f2c-0a8652976706_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PropertyPlantAndEquipmentTypeDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentByTypeAxis_f95f5cac-aefb-4097-8f2c-0a8652976706" xlink:to="loc_us-gaap_PropertyPlantAndEquipmentTypeDomain_f95f5cac-aefb-4097-8f2c-0a8652976706_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentTypeDomain_0f3be96b-00c2-4fb9-89c0-30a3b00bfa88" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PropertyPlantAndEquipmentTypeDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentByTypeAxis_f95f5cac-aefb-4097-8f2c-0a8652976706" xlink:to="loc_us-gaap_PropertyPlantAndEquipmentTypeDomain_0f3be96b-00c2-4fb9-89c0-30a3b00bfa88" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SoftwareDevelopmentMember_ccf473dd-b0ac-4d3d-9d47-fa043f423e42" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_SoftwareDevelopmentMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentTypeDomain_0f3be96b-00c2-4fb9-89c0-30a3b00bfa88" xlink:to="loc_us-gaap_SoftwareDevelopmentMember_ccf473dd-b0ac-4d3d-9d47-fa043f423e42" xlink:type="arc" order="0"/>
  </link:definitionLink>
  <link:roleRef roleURI="http://www.overstock.com/role/PROPERTYANDEQUIPMENTNETDepreciationExpenseDetails" xlink:type="simple" xlink:href="ostk-20230630.xsd#PROPERTYANDEQUIPMENTNETDepreciationExpenseDetails"/>
  <link:definitionLink xlink:role="http://www.overstock.com/role/PROPERTYANDEQUIPMENTNETDepreciationExpenseDetails" xlink:type="extended" id="i9c02e4c3969d4cae872aa5d512f4f0ba_PROPERTYANDEQUIPMENTNETDepreciationExpenseDetails">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentLineItems_3c61a451-d3dc-4065-ab1b-47014d58d741" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PropertyPlantAndEquipmentLineItems"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Depreciation_c4ecb14d-d8b1-40da-8a61-97c36753ab1d" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_Depreciation"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentLineItems_3c61a451-d3dc-4065-ab1b-47014d58d741" xlink:to="loc_us-gaap_Depreciation_c4ecb14d-d8b1-40da-8a61-97c36753ab1d" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfPropertyPlantAndEquipmentTable_768b2fb4-0c7f-45b1-b480-ad83b0e1ead7" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfPropertyPlantAndEquipmentTable"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/all" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentLineItems_3c61a451-d3dc-4065-ab1b-47014d58d741" xlink:to="loc_us-gaap_ScheduleOfPropertyPlantAndEquipmentTable_768b2fb4-0c7f-45b1-b480-ad83b0e1ead7" xlink:type="arc" order="1" xbrldt:closed="true" xbrldt:contextElement="segment"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeStatementLocationAxis_68ea3ca6-6629-4be4-bedc-cc0f6ff07202" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IncomeStatementLocationAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_ScheduleOfPropertyPlantAndEquipmentTable_768b2fb4-0c7f-45b1-b480-ad83b0e1ead7" xlink:to="loc_us-gaap_IncomeStatementLocationAxis_68ea3ca6-6629-4be4-bedc-cc0f6ff07202" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeStatementLocationDomain_68ea3ca6-6629-4be4-bedc-cc0f6ff07202_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IncomeStatementLocationDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_IncomeStatementLocationAxis_68ea3ca6-6629-4be4-bedc-cc0f6ff07202" xlink:to="loc_us-gaap_IncomeStatementLocationDomain_68ea3ca6-6629-4be4-bedc-cc0f6ff07202_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeStatementLocationDomain_edb968c2-f1b7-44d5-bf92-c65874425ff5" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IncomeStatementLocationDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_IncomeStatementLocationAxis_68ea3ca6-6629-4be4-bedc-cc0f6ff07202" xlink:to="loc_us-gaap_IncomeStatementLocationDomain_edb968c2-f1b7-44d5-bf92-c65874425ff5" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CostOfSalesMember_e01afcce-1a9e-4379-8438-6cd0d96b9bd8" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_CostOfSalesMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncomeStatementLocationDomain_edb968c2-f1b7-44d5-bf92-c65874425ff5" xlink:to="loc_us-gaap_CostOfSalesMember_e01afcce-1a9e-4379-8438-6cd0d96b9bd8" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_TechnologyMember_11174296-484b-42ab-968e-d8071273458e" xlink:href="ostk-20230630.xsd#ostk_TechnologyMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncomeStatementLocationDomain_edb968c2-f1b7-44d5-bf92-c65874425ff5" xlink:to="loc_ostk_TechnologyMember_11174296-484b-42ab-968e-d8071273458e" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GeneralAndAdministrativeExpenseMember_71f4e4be-86ef-4af3-bce4-2e5fc66255cd" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_GeneralAndAdministrativeExpenseMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncomeStatementLocationDomain_edb968c2-f1b7-44d5-bf92-c65874425ff5" xlink:to="loc_us-gaap_GeneralAndAdministrativeExpenseMember_71f4e4be-86ef-4af3-bce4-2e5fc66255cd" xlink:type="arc" order="2"/>
  </link:definitionLink>
  <link:roleRef roleURI="http://www.overstock.com/role/INTANGIBLEASSETSNETNarrativeDetails" xlink:type="simple" xlink:href="ostk-20230630.xsd#INTANGIBLEASSETSNETNarrativeDetails"/>
  <link:definitionLink xlink:role="http://www.overstock.com/role/INTANGIBLEASSETSNETNarrativeDetails" xlink:type="extended" id="ie0f7ebdcb6cb4bdd825f73e13352cb97_INTANGIBLEASSETSNETNarrativeDetails">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassLineItems_4d977d10-8195-461c-8120-c57bc75ab991" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassLineItems"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefinitelivedIntangibleAssetsAcquired_2c080cd3-8735-417c-9900-6d04d962c48d" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IndefinitelivedIntangibleAssetsAcquired"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassLineItems_4d977d10-8195-461c-8120-c57bc75ab991" xlink:to="loc_us-gaap_IndefinitelivedIntangibleAssetsAcquired_2c080cd3-8735-417c-9900-6d04d962c48d" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfIndefiniteLivedIntangibleAssetsTable_c52f14d5-3e4b-4105-98b4-82997070be9a" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfIndefiniteLivedIntangibleAssetsTable"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/all" xlink:from="loc_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassLineItems_4d977d10-8195-461c-8120-c57bc75ab991" xlink:to="loc_us-gaap_ScheduleOfIndefiniteLivedIntangibleAssetsTable_c52f14d5-3e4b-4105-98b4-82997070be9a" xlink:type="arc" order="1" xbrldt:closed="true" xbrldt:contextElement="segment"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis_07021eb0-d597-4933-9319-f97bccb22052" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_ScheduleOfIndefiniteLivedIntangibleAssetsTable_c52f14d5-3e4b-4105-98b4-82997070be9a" xlink:to="loc_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis_07021eb0-d597-4933-9319-f97bccb22052" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain_07021eb0-d597-4933-9319-f97bccb22052_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis_07021eb0-d597-4933-9319-f97bccb22052" xlink:to="loc_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain_07021eb0-d597-4933-9319-f97bccb22052_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain_c16c18af-de98-412f-b5b9-5c231313d85d" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis_07021eb0-d597-4933-9319-f97bccb22052" xlink:to="loc_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain_c16c18af-de98-412f-b5b9-5c231313d85d" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TradeNamesMember_1a286aad-1a26-4cf5-be87-5323ac0d0082" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_TradeNamesMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain_c16c18af-de98-412f-b5b9-5c231313d85d" xlink:to="loc_us-gaap_TradeNamesMember_1a286aad-1a26-4cf5-be87-5323ac0d0082" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsLineItems_dd8a1eda-335c-4757-8b5a-4ee829d15f02" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FiniteLivedIntangibleAssetsLineItems"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinitelivedIntangibleAssetsAcquired1_14052352-6861-4e45-b412-4293a3fc01bc" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FinitelivedIntangibleAssetsAcquired1"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsLineItems_dd8a1eda-335c-4757-8b5a-4ee829d15f02" xlink:to="loc_us-gaap_FinitelivedIntangibleAssetsAcquired1_14052352-6861-4e45-b412-4293a3fc01bc" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetUsefulLife_3027455d-7bfb-431c-8fed-09301b9e0c96" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FiniteLivedIntangibleAssetUsefulLife"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsLineItems_dd8a1eda-335c-4757-8b5a-4ee829d15f02" xlink:to="loc_us-gaap_FiniteLivedIntangibleAssetUsefulLife_3027455d-7bfb-431c-8fed-09301b9e0c96" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable_51f9f818-4320-4551-9500-10d86fabc7ec" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/all" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsLineItems_dd8a1eda-335c-4757-8b5a-4ee829d15f02" xlink:to="loc_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable_51f9f818-4320-4551-9500-10d86fabc7ec" xlink:type="arc" order="2" xbrldt:closed="true" xbrldt:contextElement="segment"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis_9aebd4bd-1f5a-4617-a43c-635b5a854006" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable_51f9f818-4320-4551-9500-10d86fabc7ec" xlink:to="loc_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis_9aebd4bd-1f5a-4617-a43c-635b5a854006" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain_9aebd4bd-1f5a-4617-a43c-635b5a854006_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis_9aebd4bd-1f5a-4617-a43c-635b5a854006" xlink:to="loc_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain_9aebd4bd-1f5a-4617-a43c-635b5a854006_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain_f391880b-a616-4d19-9789-fdf0896b6bd2" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis_9aebd4bd-1f5a-4617-a43c-635b5a854006" xlink:to="loc_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain_f391880b-a616-4d19-9789-fdf0896b6bd2" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CustomerListsMember_29e2908c-df0b-4679-a8ef-f0e450a514b3" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_CustomerListsMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain_f391880b-a616-4d19-9789-fdf0896b6bd2" xlink:to="loc_us-gaap_CustomerListsMember_29e2908c-df0b-4679-a8ef-f0e450a514b3" xlink:type="arc" order="0"/>
  </link:definitionLink>
  <link:roleRef roleURI="http://www.overstock.com/role/EQUITYSECURITIESSummaryOfEquitySecuritiesDetails" xlink:type="simple" xlink:href="ostk-20230630.xsd#EQUITYSECURITIESSummaryOfEquitySecuritiesDetails"/>
  <link:definitionLink xlink:role="http://www.overstock.com/role/EQUITYSECURITIESSummaryOfEquitySecuritiesDetails" xlink:type="extended" id="i89d7b8faca444a048241ff7341f3323d_EQUITYSECURITIESSummaryOfEquitySecuritiesDetails">
    <link:loc xlink:type="locator" xlink:label="loc_ostk_ScheduleOfEquitySecuritiesLineItems_93ac1e4e-d6ac-43f5-84d0-2b4e1b9b32f8" xlink:href="ostk-20230630.xsd#ostk_ScheduleOfEquitySecuritiesLineItems"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestments_1cb1ebca-6236-4b99-935b-1b4258743fa6" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EquityMethodInvestments"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_ostk_ScheduleOfEquitySecuritiesLineItems_93ac1e4e-d6ac-43f5-84d0-2b4e1b9b32f8" xlink:to="loc_us-gaap_EquityMethodInvestments_1cb1ebca-6236-4b99-935b-1b4258743fa6" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFVNINoncurrent_88469f01-7205-4827-b5ea-217531545cf4" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EquitySecuritiesFVNINoncurrent"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_ostk_ScheduleOfEquitySecuritiesLineItems_93ac1e4e-d6ac-43f5-84d0-2b4e1b9b32f8" xlink:to="loc_us-gaap_EquitySecuritiesFVNINoncurrent_88469f01-7205-4827-b5ea-217531545cf4" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermInvestments_4e45aec9-9644-4e05-ba8b-0afc8d5328f4" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LongTermInvestments"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_ostk_ScheduleOfEquitySecuritiesLineItems_93ac1e4e-d6ac-43f5-84d0-2b4e1b9b32f8" xlink:to="loc_us-gaap_LongTermInvestments_4e45aec9-9644-4e05-ba8b-0afc8d5328f4" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentOwnershipPercentage_9943bb1f-8039-4354-a933-6299861cc0a1" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EquityMethodInvestmentOwnershipPercentage"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_ostk_ScheduleOfEquitySecuritiesLineItems_93ac1e4e-d6ac-43f5-84d0-2b4e1b9b32f8" xlink:to="loc_us-gaap_EquityMethodInvestmentOwnershipPercentage_9943bb1f-8039-4354-a933-6299861cc0a1" xlink:type="arc" order="3"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_ScheduleOfEquitySecuritiesTable_04a56f17-3235-41de-92e1-36a50cc18310" xlink:href="ostk-20230630.xsd#ostk_ScheduleOfEquitySecuritiesTable"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/all" xlink:from="loc_ostk_ScheduleOfEquitySecuritiesLineItems_93ac1e4e-d6ac-43f5-84d0-2b4e1b9b32f8" xlink:to="loc_ostk_ScheduleOfEquitySecuritiesTable_04a56f17-3235-41de-92e1-36a50cc18310" xlink:type="arc" order="1" xbrldt:closed="true" xbrldt:contextElement="segment"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByFairValueHierarchyLevelAxis_9ebcb56c-599b-4ec7-8566-8107ee678908" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueByFairValueHierarchyLevelAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_ostk_ScheduleOfEquitySecuritiesTable_04a56f17-3235-41de-92e1-36a50cc18310" xlink:to="loc_us-gaap_FairValueByFairValueHierarchyLevelAxis_9ebcb56c-599b-4ec7-8566-8107ee678908" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_9ebcb56c-599b-4ec7-8566-8107ee678908_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueMeasurementsFairValueHierarchyDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_FairValueByFairValueHierarchyLevelAxis_9ebcb56c-599b-4ec7-8566-8107ee678908" xlink:to="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_9ebcb56c-599b-4ec7-8566-8107ee678908_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_728758f7-c265-4435-b139-82ea6962abd0" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueMeasurementsFairValueHierarchyDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_FairValueByFairValueHierarchyLevelAxis_9ebcb56c-599b-4ec7-8566-8107ee678908" xlink:to="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_728758f7-c265-4435-b139-82ea6962abd0" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel3Member_b919698b-1041-42a1-b12a-4f5792cd2872" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueInputsLevel3Member"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_728758f7-c265-4435-b139-82ea6962abd0" xlink:to="loc_us-gaap_FairValueInputsLevel3Member_b919698b-1041-42a1-b12a-4f5792cd2872" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel1Member_9b0e2ec9-774f-45ab-ab9a-ae64044f140f" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueInputsLevel1Member"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_728758f7-c265-4435-b139-82ea6962abd0" xlink:to="loc_us-gaap_FairValueInputsLevel1Member_9b0e2ec9-774f-45ab-ab9a-ae64044f140f" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByMeasurementFrequencyAxis_ceaabe22-3cda-4228-a6aa-75e47b750a5c" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueByMeasurementFrequencyAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_ostk_ScheduleOfEquitySecuritiesTable_04a56f17-3235-41de-92e1-36a50cc18310" xlink:to="loc_us-gaap_FairValueByMeasurementFrequencyAxis_ceaabe22-3cda-4228-a6aa-75e47b750a5c" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementFrequencyDomain_ceaabe22-3cda-4228-a6aa-75e47b750a5c_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueMeasurementFrequencyDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_FairValueByMeasurementFrequencyAxis_ceaabe22-3cda-4228-a6aa-75e47b750a5c" xlink:to="loc_us-gaap_FairValueMeasurementFrequencyDomain_ceaabe22-3cda-4228-a6aa-75e47b750a5c_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementFrequencyDomain_c59927be-b903-4c48-8481-376935d6e53c" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueMeasurementFrequencyDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_FairValueByMeasurementFrequencyAxis_ceaabe22-3cda-4228-a6aa-75e47b750a5c" xlink:to="loc_us-gaap_FairValueMeasurementFrequencyDomain_c59927be-b903-4c48-8481-376935d6e53c" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementsRecurringMember_b103f95b-ee95-41b6-8c91-97c874aa9573" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueMeasurementsRecurringMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_FairValueMeasurementFrequencyDomain_c59927be-b903-4c48-8481-376935d6e53c" xlink:to="loc_us-gaap_FairValueMeasurementsRecurringMember_b103f95b-ee95-41b6-8c91-97c874aa9573" xlink:type="arc" order="0"/>
  </link:definitionLink>
  <link:roleRef roleURI="http://www.overstock.com/role/EQUITYSECURITIESDetailsAdditionalInformationDetails" xlink:type="simple" xlink:href="ostk-20230630.xsd#EQUITYSECURITIESDetailsAdditionalInformationDetails"/>
  <link:definitionLink xlink:role="http://www.overstock.com/role/EQUITYSECURITIESDetailsAdditionalInformationDetails" xlink:type="extended" id="ic3dfc1208bbe4c299c26cbf36198e440_EQUITYSECURITIESDetailsAdditionalInformationDetails">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems_2eff3dd7-b05f-4274-aa84-c5d5cc59a942" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfEquityMethodInvestmentsLineItems"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermInvestments_ae15ba2c-e751-4760-b290-319647575eed" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LongTermInvestments"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems_2eff3dd7-b05f-4274-aa84-c5d5cc59a942" xlink:to="loc_us-gaap_LongTermInvestments_ae15ba2c-e751-4760-b290-319647575eed" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFVNINoncurrent_06b631e8-4b68-4eaa-bdb0-285f026de79b" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EquitySecuritiesFVNINoncurrent"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems_2eff3dd7-b05f-4274-aa84-c5d5cc59a942" xlink:to="loc_us-gaap_EquitySecuritiesFVNINoncurrent_06b631e8-4b68-4eaa-bdb0-285f026de79b" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEquityMethodInvestmentsTable_facd7691-5fe0-4796-a7f1-1747176e9d66" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfEquityMethodInvestmentsTable"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/all" xlink:from="loc_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems_2eff3dd7-b05f-4274-aa84-c5d5cc59a942" xlink:to="loc_us-gaap_ScheduleOfEquityMethodInvestmentsTable_facd7691-5fe0-4796-a7f1-1747176e9d66" xlink:type="arc" order="1" xbrldt:closed="true" xbrldt:contextElement="segment"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByMeasurementFrequencyAxis_82ee6934-922e-415d-a02d-f24c44009b06" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueByMeasurementFrequencyAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_ScheduleOfEquityMethodInvestmentsTable_facd7691-5fe0-4796-a7f1-1747176e9d66" xlink:to="loc_us-gaap_FairValueByMeasurementFrequencyAxis_82ee6934-922e-415d-a02d-f24c44009b06" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementFrequencyDomain_82ee6934-922e-415d-a02d-f24c44009b06_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueMeasurementFrequencyDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_FairValueByMeasurementFrequencyAxis_82ee6934-922e-415d-a02d-f24c44009b06" xlink:to="loc_us-gaap_FairValueMeasurementFrequencyDomain_82ee6934-922e-415d-a02d-f24c44009b06_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementFrequencyDomain_c2eec84a-5d90-4db6-afc5-a2d9f28c7912" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueMeasurementFrequencyDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_FairValueByMeasurementFrequencyAxis_82ee6934-922e-415d-a02d-f24c44009b06" xlink:to="loc_us-gaap_FairValueMeasurementFrequencyDomain_c2eec84a-5d90-4db6-afc5-a2d9f28c7912" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementsRecurringMember_173df26d-1921-4c8a-a82c-16e5af11753f" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueMeasurementsRecurringMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_FairValueMeasurementFrequencyDomain_c2eec84a-5d90-4db6-afc5-a2d9f28c7912" xlink:to="loc_us-gaap_FairValueMeasurementsRecurringMember_173df26d-1921-4c8a-a82c-16e5af11753f" xlink:type="arc" order="0"/>
  </link:definitionLink>
  <link:roleRef roleURI="http://www.overstock.com/role/EQUITYSECURITIESEquitySecuritiesAccountedUnderASC323AndOwnershipInterestDetails" xlink:type="simple" xlink:href="ostk-20230630.xsd#EQUITYSECURITIESEquitySecuritiesAccountedUnderASC323AndOwnershipInterestDetails"/>
  <link:definitionLink xlink:role="http://www.overstock.com/role/EQUITYSECURITIESEquitySecuritiesAccountedUnderASC323AndOwnershipInterestDetails" xlink:type="extended" id="ie6e0a8c9e0f1490bb35edf17bc11cf7f_EQUITYSECURITIESEquitySecuritiesAccountedUnderASC323AndOwnershipInterestDetails">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems_36495cd1-face-454e-a3b5-a7493e26e512" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfEquityMethodInvestmentsLineItems"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPMembersOrLimitedPartnersOwnershipInterest_f5ad689b-079f-4927-92ce-38ada1f79ec2" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPMembersOrLimitedPartnersOwnershipInterest"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems_36495cd1-face-454e-a3b5-a7493e26e512" xlink:to="loc_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPMembersOrLimitedPartnersOwnershipInterest_f5ad689b-079f-4927-92ce-38ada1f79ec2" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentOwnershipPercentage_94eaf71f-7e9b-40b4-893d-6950049be78d" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EquityMethodInvestmentOwnershipPercentage"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems_36495cd1-face-454e-a3b5-a7493e26e512" xlink:to="loc_us-gaap_EquityMethodInvestmentOwnershipPercentage_94eaf71f-7e9b-40b4-893d-6950049be78d" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEquityMethodInvestmentsTable_4b2b0772-900a-4f64-a25f-acd55ef4ebab" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfEquityMethodInvestmentsTable"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/all" xlink:from="loc_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems_36495cd1-face-454e-a3b5-a7493e26e512" xlink:to="loc_us-gaap_ScheduleOfEquityMethodInvestmentsTable_4b2b0772-900a-4f64-a25f-acd55ef4ebab" xlink:type="arc" order="1" xbrldt:closed="true" xbrldt:contextElement="segment"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_LegalEntityAxis_7732c594-8b5d-4d52-8231-9c7b818f171b" xlink:href="https://xbrl.sec.gov/dei/2023/dei-2023.xsd#dei_LegalEntityAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_ScheduleOfEquityMethodInvestmentsTable_4b2b0772-900a-4f64-a25f-acd55ef4ebab" xlink:to="loc_dei_LegalEntityAxis_7732c594-8b5d-4d52-8231-9c7b818f171b" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityDomain_7732c594-8b5d-4d52-8231-9c7b818f171b_default" xlink:href="https://xbrl.sec.gov/dei/2023/dei-2023.xsd#dei_EntityDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_dei_LegalEntityAxis_7732c594-8b5d-4d52-8231-9c7b818f171b" xlink:to="loc_dei_EntityDomain_7732c594-8b5d-4d52-8231-9c7b818f171b_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityDomain_400d739a-64df-44e5-8707-d350938c3f67" xlink:href="https://xbrl.sec.gov/dei/2023/dei-2023.xsd#dei_EntityDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_dei_LegalEntityAxis_7732c594-8b5d-4d52-8231-9c7b818f171b" xlink:to="loc_dei_EntityDomain_400d739a-64df-44e5-8707-d350938c3f67" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_OverstockcomIncMember_4be385f7-79fb-481b-9547-c96d33dc6766" xlink:href="ostk-20230630.xsd#ostk_OverstockcomIncMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_dei_EntityDomain_400d739a-64df-44e5-8707-d350938c3f67" xlink:to="loc_ostk_OverstockcomIncMember_4be385f7-79fb-481b-9547-c96d33dc6766" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis_09cea7a3-9b47-44f1-a0ce-6337b8c4ce1d" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_ScheduleOfEquityMethodInvestmentsTable_4b2b0772-900a-4f64-a25f-acd55ef4ebab" xlink:to="loc_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis_09cea7a3-9b47-44f1-a0ce-6337b8c4ce1d" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_srt_EquityMethodInvesteeNameDomain_09cea7a3-9b47-44f1-a0ce-6337b8c4ce1d_default" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_EquityMethodInvesteeNameDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis_09cea7a3-9b47-44f1-a0ce-6337b8c4ce1d" xlink:to="loc_srt_EquityMethodInvesteeNameDomain_09cea7a3-9b47-44f1-a0ce-6337b8c4ce1d_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_srt_EquityMethodInvesteeNameDomain_c502cf99-d112-4017-878c-a005c5d98e32" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_EquityMethodInvesteeNameDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis_09cea7a3-9b47-44f1-a0ce-6337b8c4ce1d" xlink:to="loc_srt_EquityMethodInvesteeNameDomain_c502cf99-d112-4017-878c-a005c5d98e32" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_TZero.comInc.Member_e35c8b80-43eb-4b67-b3a5-dd7cf4105a27" xlink:href="ostk-20230630.xsd#ostk_TZero.comInc.Member"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_srt_EquityMethodInvesteeNameDomain_c502cf99-d112-4017-878c-a005c5d98e32" xlink:to="loc_ostk_TZero.comInc.Member_e35c8b80-43eb-4b67-b3a5-dd7cf4105a27" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_SpeedRouteLLCMember_f42730ea-6692-47d6-9ec7-4023edc9b7c1" xlink:href="ostk-20230630.xsd#ostk_SpeedRouteLLCMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_srt_EquityMethodInvesteeNameDomain_c502cf99-d112-4017-878c-a005c5d98e32" xlink:to="loc_ostk_SpeedRouteLLCMember_f42730ea-6692-47d6-9ec7-4023edc9b7c1" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_srt_OwnershipAxis_bba0fde9-82e5-4f6e-a408-a058ead2fc65" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_OwnershipAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_ScheduleOfEquityMethodInvestmentsTable_4b2b0772-900a-4f64-a25f-acd55ef4ebab" xlink:to="loc_srt_OwnershipAxis_bba0fde9-82e5-4f6e-a408-a058ead2fc65" xlink:type="arc" order="3"/>
    <link:loc xlink:type="locator" xlink:label="loc_srt_OwnershipDomain_bba0fde9-82e5-4f6e-a408-a058ead2fc65_default" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_OwnershipDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_srt_OwnershipAxis_bba0fde9-82e5-4f6e-a408-a058ead2fc65" xlink:to="loc_srt_OwnershipDomain_bba0fde9-82e5-4f6e-a408-a058ead2fc65_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_srt_OwnershipDomain_3b0917d6-243a-49e7-9c41-77121e11a299" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_OwnershipDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_srt_OwnershipAxis_bba0fde9-82e5-4f6e-a408-a058ead2fc65" xlink:to="loc_srt_OwnershipDomain_3b0917d6-243a-49e7-9c41-77121e11a299" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_MediciVenturesLPMember_1995c0a5-f0a2-4235-b81a-d09d6899f19d" xlink:href="ostk-20230630.xsd#ostk_MediciVenturesLPMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_srt_OwnershipDomain_3b0917d6-243a-49e7-9c41-77121e11a299" xlink:to="loc_ostk_MediciVenturesLPMember_1995c0a5-f0a2-4235-b81a-d09d6899f19d" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_srt_RangeAxis_569656f0-087d-4bce-ab9a-9c28a498e461" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_RangeAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_ScheduleOfEquityMethodInvestmentsTable_4b2b0772-900a-4f64-a25f-acd55ef4ebab" xlink:to="loc_srt_RangeAxis_569656f0-087d-4bce-ab9a-9c28a498e461" xlink:type="arc" order="4"/>
    <link:loc xlink:type="locator" xlink:label="loc_srt_RangeMember_569656f0-087d-4bce-ab9a-9c28a498e461_default" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_RangeMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_srt_RangeAxis_569656f0-087d-4bce-ab9a-9c28a498e461" xlink:to="loc_srt_RangeMember_569656f0-087d-4bce-ab9a-9c28a498e461_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_srt_RangeMember_2fd5ffe2-1a71-4bda-bdec-e1109d607dad" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_RangeMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_srt_RangeAxis_569656f0-087d-4bce-ab9a-9c28a498e461" xlink:to="loc_srt_RangeMember_2fd5ffe2-1a71-4bda-bdec-e1109d607dad" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_srt_MinimumMember_d484c16d-39eb-4a0a-a312-4bc1ced2557d" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_MinimumMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_srt_RangeMember_2fd5ffe2-1a71-4bda-bdec-e1109d607dad" xlink:to="loc_srt_MinimumMember_d484c16d-39eb-4a0a-a312-4bc1ced2557d" xlink:type="arc" order="0"/>
  </link:definitionLink>
  <link:roleRef roleURI="http://www.overstock.com/role/EQUITYSECURITIESSummarizedFinancialInformationDetails" xlink:type="simple" xlink:href="ostk-20230630.xsd#EQUITYSECURITIESSummarizedFinancialInformationDetails"/>
  <link:definitionLink xlink:role="http://www.overstock.com/role/EQUITYSECURITIESSummarizedFinancialInformationDetails" xlink:type="extended" id="id80b06fbd40b4336a6e7ebeb669fd756_EQUITYSECURITIESSummarizedFinancialInformationDetails">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems_e865fb92-a250-4ed0-906d-c2a0a684806b" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfEquityMethodInvestmentsLineItems"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeStatementAbstract_c9584db7-274f-416b-a929-c68b320ada76" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IncomeStatementAbstract"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems_e865fb92-a250-4ed0-906d-c2a0a684806b" xlink:to="loc_us-gaap_IncomeStatementAbstract_c9584db7-274f-416b-a929-c68b320ada76" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Revenues_2ed0814d-cf00-4009-b1cf-5339bc922b8a" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_Revenues"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncomeStatementAbstract_c9584db7-274f-416b-a929-c68b320ada76" xlink:to="loc_us-gaap_Revenues_2ed0814d-cf00-4009-b1cf-5339bc922b8a" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossAttributableToParent_11c69135-40fb-4d30-a8e2-a25e93a0a876" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IncomeLossAttributableToParent"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncomeStatementAbstract_c9584db7-274f-416b-a929-c68b320ada76" xlink:to="loc_us-gaap_IncomeLossAttributableToParent_11c69135-40fb-4d30-a8e2-a25e93a0a876" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss_8cef3d6c-7ae9-4726-9da7-e408fdf923c5" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_NetIncomeLoss"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncomeStatementAbstract_c9584db7-274f-416b-a929-c68b320ada76" xlink:to="loc_us-gaap_NetIncomeLoss_8cef3d6c-7ae9-4726-9da7-e408fdf923c5" xlink:type="arc" order="3"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEquityMethodInvestmentsTable_dcae31ec-ed38-4833-92c8-90e06c0c5e9b" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfEquityMethodInvestmentsTable"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/all" xlink:from="loc_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems_e865fb92-a250-4ed0-906d-c2a0a684806b" xlink:to="loc_us-gaap_ScheduleOfEquityMethodInvestmentsTable_dcae31ec-ed38-4833-92c8-90e06c0c5e9b" xlink:type="arc" order="1" xbrldt:closed="true" xbrldt:contextElement="segment"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis_19f7c605-6154-4899-b3da-a4b42c305b37" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_ScheduleOfEquityMethodInvestmentsTable_dcae31ec-ed38-4833-92c8-90e06c0c5e9b" xlink:to="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis_19f7c605-6154-4899-b3da-a4b42c305b37" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain_19f7c605-6154-4899-b3da-a4b42c305b37_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis_19f7c605-6154-4899-b3da-a4b42c305b37" xlink:to="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain_19f7c605-6154-4899-b3da-a4b42c305b37_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain_0404618c-154b-40d7-bea9-0983fb835b3e" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis_19f7c605-6154-4899-b3da-a4b42c305b37" xlink:to="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain_0404618c-154b-40d7-bea9-0983fb835b3e" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_TZero.comInc.Member_13285a23-d339-4924-aefc-ab11aabd27d9" xlink:href="ostk-20230630.xsd#ostk_TZero.comInc.Member"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain_0404618c-154b-40d7-bea9-0983fb835b3e" xlink:to="loc_ostk_TZero.comInc.Member_13285a23-d339-4924-aefc-ab11aabd27d9" xlink:type="arc" order="0"/>
  </link:definitionLink>
  <link:roleRef roleURI="http://www.overstock.com/role/BORROWINGSDetails" xlink:type="simple" xlink:href="ostk-20230630.xsd#BORROWINGSDetails"/>
  <link:definitionLink xlink:role="http://www.overstock.com/role/BORROWINGSDetails" xlink:type="extended" id="i0cc894a6ab2144e99f1888a8bb4abb0f_BORROWINGSDetails">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentLineItems_9e6b35fd-a754-48ad-addd-99771134fb2b" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtInstrumentLineItems"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebt_68349e39-be65-4602-b45a-c972531fba3a" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LongTermDebt"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_DebtInstrumentLineItems_9e6b35fd-a754-48ad-addd-99771134fb2b" xlink:to="loc_us-gaap_LongTermDebt_68349e39-be65-4602-b45a-c972531fba3a" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentInterestRateStatedPercentage_dbe40a35-f91e-4e03-8f2f-44d9a7e7ed92" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtInstrumentInterestRateStatedPercentage"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_DebtInstrumentLineItems_9e6b35fd-a754-48ad-addd-99771134fb2b" xlink:to="loc_us-gaap_DebtInstrumentInterestRateStatedPercentage_dbe40a35-f91e-4e03-8f2f-44d9a7e7ed92" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtTerm_eb0b6d9a-8289-4dfe-a6a6-fd40c2d9a57a" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LongTermDebtTerm"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_DebtInstrumentLineItems_9e6b35fd-a754-48ad-addd-99771134fb2b" xlink:to="loc_us-gaap_LongTermDebtTerm_eb0b6d9a-8289-4dfe-a6a6-fd40c2d9a57a" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_LongtermDebtPrincipalandInterestOnlyPayments_fbf69cdf-52d2-4ed5-b6e3-15085b4dd8a9" xlink:href="ostk-20230630.xsd#ostk_LongtermDebtPrincipalandInterestOnlyPayments"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_DebtInstrumentLineItems_9e6b35fd-a754-48ad-addd-99771134fb2b" xlink:to="loc_ostk_LongtermDebtPrincipalandInterestOnlyPayments_fbf69cdf-52d2-4ed5-b6e3-15085b4dd8a9" xlink:type="arc" order="3"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_SeniorMezzanineNoteTotalOutstanding_d7783466-c64a-400b-9cc7-0ee9c4939d70" xlink:href="ostk-20230630.xsd#ostk_SeniorMezzanineNoteTotalOutstanding"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_DebtInstrumentLineItems_9e6b35fd-a754-48ad-addd-99771134fb2b" xlink:to="loc_ostk_SeniorMezzanineNoteTotalOutstanding_d7783466-c64a-400b-9cc7-0ee9c4939d70" xlink:type="arc" order="4"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredFinanceCostsNet_f157fd10-c82c-41c3-97c2-ee922766d3a7" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DeferredFinanceCostsNet"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_DebtInstrumentLineItems_9e6b35fd-a754-48ad-addd-99771134fb2b" xlink:to="loc_us-gaap_DeferredFinanceCostsNet_f157fd10-c82c-41c3-97c2-ee922766d3a7" xlink:type="arc" order="5"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_SeniorMezzanineNoteCurrentLiabilities_19b0cf03-f300-4f37-8edb-02d4a1a53312" xlink:href="ostk-20230630.xsd#ostk_SeniorMezzanineNoteCurrentLiabilities"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_DebtInstrumentLineItems_9e6b35fd-a754-48ad-addd-99771134fb2b" xlink:to="loc_ostk_SeniorMezzanineNoteCurrentLiabilities_19b0cf03-f300-4f37-8edb-02d4a1a53312" xlink:type="arc" order="6"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_NetWorthRequiredForComplianceMinimum_fe800bd7-3f5a-4fb5-ba7e-e80f88caa85a" xlink:href="ostk-20230630.xsd#ostk_NetWorthRequiredForComplianceMinimum"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_DebtInstrumentLineItems_9e6b35fd-a754-48ad-addd-99771134fb2b" xlink:to="loc_ostk_NetWorthRequiredForComplianceMinimum_fe800bd7-3f5a-4fb5-ba7e-e80f88caa85a" xlink:type="arc" order="7"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_MinimumLiquidAssets_2f8317c7-4988-427d-8c6c-2b1bced2c967" xlink:href="ostk-20230630.xsd#ostk_MinimumLiquidAssets"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_DebtInstrumentLineItems_9e6b35fd-a754-48ad-addd-99771134fb2b" xlink:to="loc_ostk_MinimumLiquidAssets_2f8317c7-4988-427d-8c6c-2b1bced2c967" xlink:type="arc" order="8"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_MinimumNetWorthRequiredforMezzanineNoteDuration_d643aa1f-8967-448b-9838-21fef54e524d" xlink:href="ostk-20230630.xsd#ostk_MinimumNetWorthRequiredforMezzanineNoteDuration"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_DebtInstrumentLineItems_9e6b35fd-a754-48ad-addd-99771134fb2b" xlink:to="loc_ostk_MinimumNetWorthRequiredforMezzanineNoteDuration_d643aa1f-8967-448b-9838-21fef54e524d" xlink:type="arc" order="9"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_MinimumLiquidAssetsComplianceforDurationofMezzanineNote_a52d3dcf-1b4b-4131-9762-064029583eef" xlink:href="ostk-20230630.xsd#ostk_MinimumLiquidAssetsComplianceforDurationofMezzanineNote"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_DebtInstrumentLineItems_9e6b35fd-a754-48ad-addd-99771134fb2b" xlink:to="loc_ostk_MinimumLiquidAssetsComplianceforDurationofMezzanineNote_a52d3dcf-1b4b-4131-9762-064029583eef" xlink:type="arc" order="10"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentTable_bd76eae6-9652-4b25-88f3-f5007d39fcb5" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtInstrumentTable"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/all" xlink:from="loc_us-gaap_DebtInstrumentLineItems_9e6b35fd-a754-48ad-addd-99771134fb2b" xlink:to="loc_us-gaap_DebtInstrumentTable_bd76eae6-9652-4b25-88f3-f5007d39fcb5" xlink:type="arc" order="1" xbrldt:closed="true" xbrldt:contextElement="segment"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentAxis_f70c2a9a-1b34-4ac1-aec9-a26348884624" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtInstrumentAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_DebtInstrumentTable_bd76eae6-9652-4b25-88f3-f5007d39fcb5" xlink:to="loc_us-gaap_DebtInstrumentAxis_f70c2a9a-1b34-4ac1-aec9-a26348884624" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentNameDomain_f70c2a9a-1b34-4ac1-aec9-a26348884624_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtInstrumentNameDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_DebtInstrumentAxis_f70c2a9a-1b34-4ac1-aec9-a26348884624" xlink:to="loc_us-gaap_DebtInstrumentNameDomain_f70c2a9a-1b34-4ac1-aec9-a26348884624_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentNameDomain_4141fe73-7308-4f0e-85fb-4aaec6f48442" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtInstrumentNameDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_DebtInstrumentAxis_f70c2a9a-1b34-4ac1-aec9-a26348884624" xlink:to="loc_us-gaap_DebtInstrumentNameDomain_4141fe73-7308-4f0e-85fb-4aaec6f48442" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_LoanCoreCapitalFundingCorporationMember_f45c0e4d-c9e8-4716-b146-a7a351158fc9" xlink:href="ostk-20230630.xsd#ostk_LoanCoreCapitalFundingCorporationMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_DebtInstrumentNameDomain_4141fe73-7308-4f0e-85fb-4aaec6f48442" xlink:to="loc_ostk_LoanCoreCapitalFundingCorporationMember_f45c0e4d-c9e8-4716-b146-a7a351158fc9" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongtermDebtTypeAxis_4ac8288f-5d71-4499-92c8-1397b2b38eb4" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LongtermDebtTypeAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_DebtInstrumentTable_bd76eae6-9652-4b25-88f3-f5007d39fcb5" xlink:to="loc_us-gaap_LongtermDebtTypeAxis_4ac8288f-5d71-4499-92c8-1397b2b38eb4" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongtermDebtTypeDomain_4ac8288f-5d71-4499-92c8-1397b2b38eb4_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LongtermDebtTypeDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_LongtermDebtTypeAxis_4ac8288f-5d71-4499-92c8-1397b2b38eb4" xlink:to="loc_us-gaap_LongtermDebtTypeDomain_4ac8288f-5d71-4499-92c8-1397b2b38eb4_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongtermDebtTypeDomain_ac90aa0b-3aaf-4ea4-9a92-d652c37d9b21" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LongtermDebtTypeDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_LongtermDebtTypeAxis_4ac8288f-5d71-4499-92c8-1397b2b38eb4" xlink:to="loc_us-gaap_LongtermDebtTypeDomain_ac90aa0b-3aaf-4ea4-9a92-d652c37d9b21" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SeniorNotesMember_619f3f8f-c63c-4b95-aec6-9d52e23cd726" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_SeniorNotesMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_LongtermDebtTypeDomain_ac90aa0b-3aaf-4ea4-9a92-d652c37d9b21" xlink:to="loc_us-gaap_SeniorNotesMember_619f3f8f-c63c-4b95-aec6-9d52e23cd726" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_MezzanineNoteMember_ce52d778-4c2b-45e7-bef2-a1afadc81455" xlink:href="ostk-20230630.xsd#ostk_MezzanineNoteMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_LongtermDebtTypeDomain_ac90aa0b-3aaf-4ea4-9a92-d652c37d9b21" xlink:to="loc_ostk_MezzanineNoteMember_ce52d778-4c2b-45e7-bef2-a1afadc81455" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_SeniorandMezzanineBlendedRateMember_e3e742d3-6eb0-4cf0-be2f-54656d9d4b1c" xlink:href="ostk-20230630.xsd#ostk_SeniorandMezzanineBlendedRateMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_LongtermDebtTypeDomain_ac90aa0b-3aaf-4ea4-9a92-d652c37d9b21" xlink:to="loc_ostk_SeniorandMezzanineBlendedRateMember_e3e742d3-6eb0-4cf0-be2f-54656d9d4b1c" xlink:type="arc" order="2"/>
  </link:definitionLink>
  <link:roleRef roleURI="http://www.overstock.com/role/LEASESAdditionalInformationDetails" xlink:type="simple" xlink:href="ostk-20230630.xsd#LEASESAdditionalInformationDetails"/>
  <link:definitionLink xlink:role="http://www.overstock.com/role/LEASESAdditionalInformationDetails" xlink:type="extended" id="i1702fe6d898d4cf394ab17609e77f523_LEASESAdditionalInformationDetails">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeLeaseDescriptionLineItems_a7c7159e-d33e-45fd-91f7-5b04427f2a2f" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LesseeLeaseDescriptionLineItems"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseRemainingLeaseTerm_a8c9940b-af91-4a58-a840-691f5fa2d5cb" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LesseeOperatingLeaseRemainingLeaseTerm"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_LesseeLeaseDescriptionLineItems_a7c7159e-d33e-45fd-91f7-5b04427f2a2f" xlink:to="loc_us-gaap_LesseeOperatingLeaseRemainingLeaseTerm_a8c9940b-af91-4a58-a840-691f5fa2d5cb" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeLeaseDescriptionTable_c8ef2814-8dbb-4c05-a82e-e2b6cfb2e94b" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LesseeLeaseDescriptionTable"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/all" xlink:from="loc_us-gaap_LesseeLeaseDescriptionLineItems_a7c7159e-d33e-45fd-91f7-5b04427f2a2f" xlink:to="loc_us-gaap_LesseeLeaseDescriptionTable_c8ef2814-8dbb-4c05-a82e-e2b6cfb2e94b" xlink:type="arc" order="1" xbrldt:closed="true" xbrldt:contextElement="segment"/>
    <link:loc xlink:type="locator" xlink:label="loc_srt_RangeAxis_5844ccd6-3648-4196-8ab5-dd01fa9784c1" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_RangeAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_LesseeLeaseDescriptionTable_c8ef2814-8dbb-4c05-a82e-e2b6cfb2e94b" xlink:to="loc_srt_RangeAxis_5844ccd6-3648-4196-8ab5-dd01fa9784c1" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_srt_RangeMember_5844ccd6-3648-4196-8ab5-dd01fa9784c1_default" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_RangeMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_srt_RangeAxis_5844ccd6-3648-4196-8ab5-dd01fa9784c1" xlink:to="loc_srt_RangeMember_5844ccd6-3648-4196-8ab5-dd01fa9784c1_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_srt_RangeMember_39e461c4-08b3-4a9f-a66f-b8b57e317ff8" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_RangeMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_srt_RangeAxis_5844ccd6-3648-4196-8ab5-dd01fa9784c1" xlink:to="loc_srt_RangeMember_39e461c4-08b3-4a9f-a66f-b8b57e317ff8" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_srt_MinimumMember_9d9db98d-2b17-4d24-be2c-f1d7ffe0668b" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_MinimumMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_srt_RangeMember_39e461c4-08b3-4a9f-a66f-b8b57e317ff8" xlink:to="loc_srt_MinimumMember_9d9db98d-2b17-4d24-be2c-f1d7ffe0668b" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_srt_MaximumMember_7adf6f30-f07b-4764-89b2-3f5b2055914e" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_MaximumMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_srt_RangeMember_39e461c4-08b3-4a9f-a66f-b8b57e317ff8" xlink:to="loc_srt_MaximumMember_7adf6f30-f07b-4764-89b2-3f5b2055914e" xlink:type="arc" order="1"/>
  </link:definitionLink>
  <link:roleRef roleURI="http://www.overstock.com/role/STOCKHOLDERSEQUITYStockRepurchaseProgramDetails" xlink:type="simple" xlink:href="ostk-20230630.xsd#STOCKHOLDERSEQUITYStockRepurchaseProgramDetails"/>
  <link:definitionLink xlink:role="http://www.overstock.com/role/STOCKHOLDERSEQUITYStockRepurchaseProgramDetails" xlink:type="extended" id="i05d40f37cadb4b5f975814fabae2eee3_STOCKHOLDERSEQUITYStockRepurchaseProgramDetails">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ClassOfStockLineItems_ed7b8304-130b-4134-858d-f7454825bf84" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ClassOfStockLineItems"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForRepurchaseOfCommonStock_4207228d-4730-4fcf-b21a-d95a7b1f41ff" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PaymentsForRepurchaseOfCommonStock"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ClassOfStockLineItems_ed7b8304-130b-4134-858d-f7454825bf84" xlink:to="loc_us-gaap_PaymentsForRepurchaseOfCommonStock_4207228d-4730-4fcf-b21a-d95a7b1f41ff" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForRepurchaseOfPreferredStockAndPreferenceStock_e45ec068-abed-4922-ae45-45e8d1a3f6fc" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PaymentsForRepurchaseOfPreferredStockAndPreferenceStock"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ClassOfStockLineItems_ed7b8304-130b-4134-858d-f7454825bf84" xlink:to="loc_us-gaap_PaymentsForRepurchaseOfPreferredStockAndPreferenceStock_e45ec068-abed-4922-ae45-45e8d1a3f6fc" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockAcquiredAverageCostPerShare_5227cd7e-e3e5-4868-88d2-cdb66e4ce18d" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_TreasuryStockAcquiredAverageCostPerShare"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ClassOfStockLineItems_ed7b8304-130b-4134-858d-f7454825bf84" xlink:to="loc_us-gaap_TreasuryStockAcquiredAverageCostPerShare_5227cd7e-e3e5-4868-88d2-cdb66e4ce18d" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockSharesRetired_2909e064-a819-4f09-8a77-b489628c892f" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_TreasuryStockSharesRetired"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ClassOfStockLineItems_ed7b8304-130b-4134-858d-f7454825bf84" xlink:to="loc_us-gaap_TreasuryStockSharesRetired_2909e064-a819-4f09-8a77-b489628c892f" xlink:type="arc" order="3"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockRepurchaseProgramRemainingAuthorizedRepurchaseAmount1_1aad85f2-1c62-413c-b77b-da0734c40938" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_StockRepurchaseProgramRemainingAuthorizedRepurchaseAmount1"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ClassOfStockLineItems_ed7b8304-130b-4134-858d-f7454825bf84" xlink:to="loc_us-gaap_StockRepurchaseProgramRemainingAuthorizedRepurchaseAmount1_1aad85f2-1c62-413c-b77b-da0734c40938" xlink:type="arc" order="4"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockRetiredCostMethodAmount_14e0e753-12d8-4edd-ad41-413b5dbe66c9" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_TreasuryStockRetiredCostMethodAmount"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ClassOfStockLineItems_ed7b8304-130b-4134-858d-f7454825bf84" xlink:to="loc_us-gaap_TreasuryStockRetiredCostMethodAmount_14e0e753-12d8-4edd-ad41-413b5dbe66c9" xlink:type="arc" order="5"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfStockByClassTable_364a68ad-40a1-4992-ab14-d6482f19fc8f" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfStockByClassTable"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/all" xlink:from="loc_us-gaap_ClassOfStockLineItems_ed7b8304-130b-4134-858d-f7454825bf84" xlink:to="loc_us-gaap_ScheduleOfStockByClassTable_364a68ad-40a1-4992-ab14-d6482f19fc8f" xlink:type="arc" order="1" xbrldt:closed="true" xbrldt:contextElement="segment"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementClassOfStockAxis_c8a1970a-259c-4a46-b340-e0299c7b0812" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_StatementClassOfStockAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_ScheduleOfStockByClassTable_364a68ad-40a1-4992-ab14-d6482f19fc8f" xlink:to="loc_us-gaap_StatementClassOfStockAxis_c8a1970a-259c-4a46-b340-e0299c7b0812" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ClassOfStockDomain_c8a1970a-259c-4a46-b340-e0299c7b0812_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ClassOfStockDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_StatementClassOfStockAxis_c8a1970a-259c-4a46-b340-e0299c7b0812" xlink:to="loc_us-gaap_ClassOfStockDomain_c8a1970a-259c-4a46-b340-e0299c7b0812_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ClassOfStockDomain_e2489044-dc96-4f79-a91f-59e8ad02c622" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ClassOfStockDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_StatementClassOfStockAxis_c8a1970a-259c-4a46-b340-e0299c7b0812" xlink:to="loc_us-gaap_ClassOfStockDomain_e2489044-dc96-4f79-a91f-59e8ad02c622" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockMember_a8cc283d-1ee6-4c36-b875-b3dd2aaf4ef2" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_CommonStockMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ClassOfStockDomain_e2489044-dc96-4f79-a91f-59e8ad02c622" xlink:to="loc_us-gaap_CommonStockMember_a8cc283d-1ee6-4c36-b875-b3dd2aaf4ef2" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_SeriesA1PreferredStockMember_fe2cfa82-ad17-47c3-a3ef-c944778c4771" xlink:href="ostk-20230630.xsd#ostk_SeriesA1PreferredStockMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ClassOfStockDomain_e2489044-dc96-4f79-a91f-59e8ad02c622" xlink:to="loc_ostk_SeriesA1PreferredStockMember_fe2cfa82-ad17-47c3-a3ef-c944778c4771" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementEquityComponentsAxis_3dbf7290-2995-4a0d-ab33-71354ee73c86" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_StatementEquityComponentsAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_ScheduleOfStockByClassTable_364a68ad-40a1-4992-ab14-d6482f19fc8f" xlink:to="loc_us-gaap_StatementEquityComponentsAxis_3dbf7290-2995-4a0d-ab33-71354ee73c86" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityComponentDomain_3dbf7290-2995-4a0d-ab33-71354ee73c86_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EquityComponentDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_StatementEquityComponentsAxis_3dbf7290-2995-4a0d-ab33-71354ee73c86" xlink:to="loc_us-gaap_EquityComponentDomain_3dbf7290-2995-4a0d-ab33-71354ee73c86_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityComponentDomain_442953b6-7d45-4890-86a4-10e5268af46b" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EquityComponentDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_StatementEquityComponentsAxis_3dbf7290-2995-4a0d-ab33-71354ee73c86" xlink:to="loc_us-gaap_EquityComponentDomain_442953b6-7d45-4890-86a4-10e5268af46b" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RetainedEarningsMember_10ede3c4-fe1c-492e-9783-2d20c5e3131d" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_RetainedEarningsMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_EquityComponentDomain_442953b6-7d45-4890-86a4-10e5268af46b" xlink:to="loc_us-gaap_RetainedEarningsMember_10ede3c4-fe1c-492e-9783-2d20c5e3131d" xlink:type="arc" order="0"/>
  </link:definitionLink>
  <link:roleRef roleURI="http://www.overstock.com/role/STOCKBASEDAWARDSStockbasedCompensationExpenseDetails" xlink:type="simple" xlink:href="ostk-20230630.xsd#STOCKBASEDAWARDSStockbasedCompensationExpenseDetails"/>
  <link:definitionLink xlink:role="http://www.overstock.com/role/STOCKBASEDAWARDSStockbasedCompensationExpenseDetails" xlink:type="extended" id="i8c5978f7d3c2476b9fc1040fdcb943f0_STOCKBASEDAWARDSStockbasedCompensationExpenseDetails">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsLineItems_ad2ec998-3847-435e-8c76-d8fd0147d730" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsLineItems"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AllocatedShareBasedCompensationExpense_10b0830d-1971-49b3-85a1-2e7035154ecb" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AllocatedShareBasedCompensationExpense"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_EmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsLineItems_ad2ec998-3847-435e-8c76-d8fd0147d730" xlink:to="loc_us-gaap_AllocatedShareBasedCompensationExpense_10b0830d-1971-49b3-85a1-2e7035154ecb" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTable_c894435b-9177-448d-8b7c-26a6540afbb4" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTable"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/all" xlink:from="loc_us-gaap_EmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsLineItems_ad2ec998-3847-435e-8c76-d8fd0147d730" xlink:to="loc_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTable_c894435b-9177-448d-8b7c-26a6540afbb4" xlink:type="arc" order="1" xbrldt:closed="true" xbrldt:contextElement="segment"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeStatementLocationAxis_17271736-5ceb-48ec-9f91-17cca9895d2f" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IncomeStatementLocationAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTable_c894435b-9177-448d-8b7c-26a6540afbb4" xlink:to="loc_us-gaap_IncomeStatementLocationAxis_17271736-5ceb-48ec-9f91-17cca9895d2f" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeStatementLocationDomain_17271736-5ceb-48ec-9f91-17cca9895d2f_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IncomeStatementLocationDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_IncomeStatementLocationAxis_17271736-5ceb-48ec-9f91-17cca9895d2f" xlink:to="loc_us-gaap_IncomeStatementLocationDomain_17271736-5ceb-48ec-9f91-17cca9895d2f_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeStatementLocationDomain_2caad365-c2ad-4801-806e-0ab197dbfb30" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IncomeStatementLocationDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_IncomeStatementLocationAxis_17271736-5ceb-48ec-9f91-17cca9895d2f" xlink:to="loc_us-gaap_IncomeStatementLocationDomain_2caad365-c2ad-4801-806e-0ab197dbfb30" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CostOfSalesMember_9a8072ee-4335-4d70-bf3d-74fa64c7065d" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_CostOfSalesMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncomeStatementLocationDomain_2caad365-c2ad-4801-806e-0ab197dbfb30" xlink:to="loc_us-gaap_CostOfSalesMember_9a8072ee-4335-4d70-bf3d-74fa64c7065d" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_SalesAndMarketingMember_3aa1af31-b7bd-4673-9092-2836a65568b4" xlink:href="ostk-20230630.xsd#ostk_SalesAndMarketingMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncomeStatementLocationDomain_2caad365-c2ad-4801-806e-0ab197dbfb30" xlink:to="loc_ostk_SalesAndMarketingMember_3aa1af31-b7bd-4673-9092-2836a65568b4" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_TechnologyMember_cc86f56b-3fa5-48b7-9e2a-43bea4d67916" xlink:href="ostk-20230630.xsd#ostk_TechnologyMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncomeStatementLocationDomain_2caad365-c2ad-4801-806e-0ab197dbfb30" xlink:to="loc_ostk_TechnologyMember_cc86f56b-3fa5-48b7-9e2a-43bea4d67916" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GeneralAndAdministrativeExpenseMember_2c6e34ab-82df-4fdb-a20e-44e79bcb2d40" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_GeneralAndAdministrativeExpenseMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_IncomeStatementLocationDomain_2caad365-c2ad-4801-806e-0ab197dbfb30" xlink:to="loc_us-gaap_GeneralAndAdministrativeExpenseMember_2c6e34ab-82df-4fdb-a20e-44e79bcb2d40" xlink:type="arc" order="3"/>
  </link:definitionLink>
  <link:roleRef roleURI="http://www.overstock.com/role/STOCKBASEDAWARDSAdditionalInformationDetails" xlink:type="simple" xlink:href="ostk-20230630.xsd#STOCKBASEDAWARDSAdditionalInformationDetails"/>
  <link:definitionLink xlink:role="http://www.overstock.com/role/STOCKBASEDAWARDSAdditionalInformationDetails" xlink:type="extended" id="ib6c6a24df46846108e5a176157218227_STOCKBASEDAWARDSAdditionalInformationDetails">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems_b0811aa3-8a9c-4d0e-a5ea-1dbe86d8179f" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_SharebasedCompensationArrangementbySharebasedPaymentAwardAwardVestingPercentage_098f3f7d-8398-4f98-95c7-6a5face09503" xlink:href="ostk-20230630.xsd#ostk_SharebasedCompensationArrangementbySharebasedPaymentAwardAwardVestingPercentage"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems_b0811aa3-8a9c-4d0e-a5ea-1dbe86d8179f" xlink:to="loc_ostk_SharebasedCompensationArrangementbySharebasedPaymentAwardAwardVestingPercentage_098f3f7d-8398-4f98-95c7-6a5face09503" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockIssuedDuringPeriodSharesEmployeeStockOwnershipPlan_05c5187a-d256-4b2d-85a9-225f817bae3c" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_StockIssuedDuringPeriodSharesEmployeeStockOwnershipPlan"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems_b0811aa3-8a9c-4d0e-a5ea-1dbe86d8179f" xlink:to="loc_us-gaap_StockIssuedDuringPeriodSharesEmployeeStockOwnershipPlan_05c5187a-d256-4b2d-85a9-225f817bae3c" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_StockIssuedDuringPeriodEmployeeStockOwnershipPlanAveragePricePerShare_151aab19-552b-4c77-b2e4-5a0f9c97375b" xlink:href="ostk-20230630.xsd#ostk_StockIssuedDuringPeriodEmployeeStockOwnershipPlanAveragePricePerShare"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems_b0811aa3-8a9c-4d0e-a5ea-1dbe86d8179f" xlink:to="loc_ostk_StockIssuedDuringPeriodEmployeeStockOwnershipPlanAveragePricePerShare_151aab19-552b-4c77-b2e4-5a0f9c97375b" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAvailableForGrant_33fccb7c-af55-4399-84ba-8cfc351e215f" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAvailableForGrant"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems_b0811aa3-8a9c-4d0e-a5ea-1dbe86d8179f" xlink:to="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAvailableForGrant_33fccb7c-af55-4399-84ba-8cfc351e215f" xlink:type="arc" order="3"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeBenefitsAndShareBasedCompensation_d6bef2d6-d2cf-4794-9148-18477cba6655" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EmployeeBenefitsAndShareBasedCompensation"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems_b0811aa3-8a9c-4d0e-a5ea-1dbe86d8179f" xlink:to="loc_us-gaap_EmployeeBenefitsAndShareBasedCompensation_d6bef2d6-d2cf-4794-9148-18477cba6655" xlink:type="arc" order="4"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable_153e5693-19b8-4c95-b73e-0ff03d50b779" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/all" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems_b0811aa3-8a9c-4d0e-a5ea-1dbe86d8179f" xlink:to="loc_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable_153e5693-19b8-4c95-b73e-0ff03d50b779" xlink:type="arc" order="1" xbrldt:closed="true" xbrldt:contextElement="segment"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AwardTypeAxis_a8b53971-a7b9-4717-a78d-afdf5210d823" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AwardTypeAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable_153e5693-19b8-4c95-b73e-0ff03d50b779" xlink:to="loc_us-gaap_AwardTypeAxis_a8b53971-a7b9-4717-a78d-afdf5210d823" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_a8b53971-a7b9-4717-a78d-afdf5210d823_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_AwardTypeAxis_a8b53971-a7b9-4717-a78d-afdf5210d823" xlink:to="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_a8b53971-a7b9-4717-a78d-afdf5210d823_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_05c989b8-5ac0-4b85-bcd9-7836710b6217" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_AwardTypeAxis_a8b53971-a7b9-4717-a78d-afdf5210d823" xlink:to="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_05c989b8-5ac0-4b85-bcd9-7836710b6217" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestrictedStockMember_5bbcfb38-ccd2-42b5-972b-f922ea21b57a" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_RestrictedStockMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_05c989b8-5ac0-4b85-bcd9-7836710b6217" xlink:to="loc_us-gaap_RestrictedStockMember_5bbcfb38-ccd2-42b5-972b-f922ea21b57a" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeStockMember_5f740341-2c97-4ec9-bd48-453283870de7" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EmployeeStockMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_05c989b8-5ac0-4b85-bcd9-7836710b6217" xlink:to="loc_us-gaap_EmployeeStockMember_5f740341-2c97-4ec9-bd48-453283870de7" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VestingAxis_00952e1e-c4c7-44c8-8507-3aab5941f5fe" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_VestingAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable_153e5693-19b8-4c95-b73e-0ff03d50b779" xlink:to="loc_us-gaap_VestingAxis_00952e1e-c4c7-44c8-8507-3aab5941f5fe" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VestingDomain_00952e1e-c4c7-44c8-8507-3aab5941f5fe_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_VestingDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_VestingAxis_00952e1e-c4c7-44c8-8507-3aab5941f5fe" xlink:to="loc_us-gaap_VestingDomain_00952e1e-c4c7-44c8-8507-3aab5941f5fe_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VestingDomain_da84e562-b630-475e-8d2d-d37f4f573097" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_VestingDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_VestingAxis_00952e1e-c4c7-44c8-8507-3aab5941f5fe" xlink:to="loc_us-gaap_VestingDomain_da84e562-b630-475e-8d2d-d37f4f573097" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_FirstYearMember_d316026c-efb9-456c-9790-1147b1c9ab08" xlink:href="ostk-20230630.xsd#ostk_FirstYearMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_VestingDomain_da84e562-b630-475e-8d2d-d37f4f573097" xlink:to="loc_ostk_FirstYearMember_d316026c-efb9-456c-9790-1147b1c9ab08" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_SecondYearMember_3e3ae7e3-8a77-4d26-91cc-aae5b75d7d74" xlink:href="ostk-20230630.xsd#ostk_SecondYearMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_VestingDomain_da84e562-b630-475e-8d2d-d37f4f573097" xlink:to="loc_ostk_SecondYearMember_3e3ae7e3-8a77-4d26-91cc-aae5b75d7d74" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_ThirdYearMember_77d37d1d-a0b9-452d-b697-405663f39431" xlink:href="ostk-20230630.xsd#ostk_ThirdYearMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_VestingDomain_da84e562-b630-475e-8d2d-d37f4f573097" xlink:to="loc_ostk_ThirdYearMember_77d37d1d-a0b9-452d-b697-405663f39431" xlink:type="arc" order="2"/>
  </link:definitionLink>
  <link:roleRef roleURI="http://www.overstock.com/role/STOCKBASEDAWARDSRestrictedStockActivityDetails" xlink:type="simple" xlink:href="ostk-20230630.xsd#STOCKBASEDAWARDSRestrictedStockActivityDetails"/>
  <link:definitionLink xlink:role="http://www.overstock.com/role/STOCKBASEDAWARDSRestrictedStockActivityDetails" xlink:type="extended" id="ie59e8e0d7a884321a19378e471a6e2db_STOCKBASEDAWARDSRestrictedStockActivityDetails">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems_4cbd67dc-825e-4011-b954-c16f2c8d52c0" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward_4581095f-e4d7-41ef-b5ad-d55580933e84" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems_4cbd67dc-825e-4011-b954-c16f2c8d52c0" xlink:to="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward_4581095f-e4d7-41ef-b5ad-d55580933e84" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber_44b4958a-8149-4bbd-8bd8-37fc7bd01382" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward_4581095f-e4d7-41ef-b5ad-d55580933e84" xlink:to="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber_44b4958a-8149-4bbd-8bd8-37fc7bd01382" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod_fe221028-2148-4979-8e2b-52300aebd1b2" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward_4581095f-e4d7-41ef-b5ad-d55580933e84" xlink:to="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod_fe221028-2148-4979-8e2b-52300aebd1b2" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod_78f7f142-ad65-4562-8c54-9c0b07d017df" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward_4581095f-e4d7-41ef-b5ad-d55580933e84" xlink:to="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod_78f7f142-ad65-4562-8c54-9c0b07d017df" xlink:type="arc" order="3"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod_77130f15-259c-4f62-91c9-0f9b8dc666d7" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward_4581095f-e4d7-41ef-b5ad-d55580933e84" xlink:to="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod_77130f15-259c-4f62-91c9-0f9b8dc666d7" xlink:type="arc" order="4"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber_091b46c9-f3cc-4189-935f-6991a28052f1" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward_705eeb30-9f0e-4b88-bc81-c0e4ddec03a4" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems_4cbd67dc-825e-4011-b954-c16f2c8d52c0" xlink:to="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward_705eeb30-9f0e-4b88-bc81-c0e4ddec03a4" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue_8c6d8cbf-8b6d-4637-b99e-bd9b5e5af19a" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward_705eeb30-9f0e-4b88-bc81-c0e4ddec03a4" xlink:to="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue_8c6d8cbf-8b6d-4637-b99e-bd9b5e5af19a" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodWeightedAverageGrantDateFairValue_f9522445-704b-498a-9f43-4e4e1ee51454" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodWeightedAverageGrantDateFairValue"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward_705eeb30-9f0e-4b88-bc81-c0e4ddec03a4" xlink:to="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodWeightedAverageGrantDateFairValue_f9522445-704b-498a-9f43-4e4e1ee51454" xlink:type="arc" order="2"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue_bf8ca57c-60d1-435e-9159-cc2b462a9415" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward_705eeb30-9f0e-4b88-bc81-c0e4ddec03a4" xlink:to="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue_bf8ca57c-60d1-435e-9159-cc2b462a9415" xlink:type="arc" order="3"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue_b42ee2fe-f997-4297-b8be-79e88f34ccd6" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward_705eeb30-9f0e-4b88-bc81-c0e4ddec03a4" xlink:to="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue_b42ee2fe-f997-4297-b8be-79e88f34ccd6" xlink:type="arc" order="4"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue_c4d9d0c3-b16e-4bcb-98ca-03dbd8c4a21c" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable_ff07b785-0ce1-49b0-ab1c-f6b4e405fa4d" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/all" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems_4cbd67dc-825e-4011-b954-c16f2c8d52c0" xlink:to="loc_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable_ff07b785-0ce1-49b0-ab1c-f6b4e405fa4d" xlink:type="arc" order="1" xbrldt:closed="true" xbrldt:contextElement="segment"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AwardTypeAxis_2e6e2b73-1137-43e0-a9cc-e5ab5a2eddd5" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AwardTypeAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable_ff07b785-0ce1-49b0-ab1c-f6b4e405fa4d" xlink:to="loc_us-gaap_AwardTypeAxis_2e6e2b73-1137-43e0-a9cc-e5ab5a2eddd5" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_2e6e2b73-1137-43e0-a9cc-e5ab5a2eddd5_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_AwardTypeAxis_2e6e2b73-1137-43e0-a9cc-e5ab5a2eddd5" xlink:to="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_2e6e2b73-1137-43e0-a9cc-e5ab5a2eddd5_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_38e607f2-2fde-48e6-898b-f43a8e15e6c3" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_AwardTypeAxis_2e6e2b73-1137-43e0-a9cc-e5ab5a2eddd5" xlink:to="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_38e607f2-2fde-48e6-898b-f43a8e15e6c3" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestrictedStockMember_a1aeca8a-02ec-4a54-9fa4-ffea41fd892a" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_RestrictedStockMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_38e607f2-2fde-48e6-898b-f43a8e15e6c3" xlink:to="loc_us-gaap_RestrictedStockMember_a1aeca8a-02ec-4a54-9fa4-ffea41fd892a" xlink:type="arc" order="0"/>
  </link:definitionLink>
  <link:roleRef roleURI="http://www.overstock.com/role/REVENUEANDCONTRACTLIABILITYNarrativeDetails" xlink:type="simple" xlink:href="ostk-20230630.xsd#REVENUEANDCONTRACTLIABILITYNarrativeDetails"/>
  <link:definitionLink xlink:role="http://www.overstock.com/role/REVENUEANDCONTRACTLIABILITYNarrativeDetails" xlink:type="extended" id="i17f17a0bd8a34d82bb1c934582dba981_REVENUEANDCONTRACTLIABILITYNarrativeDetails">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisaggregationOfRevenueLineItems_ba80fc72-3539-4843-8374-688d1f084bc2" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DisaggregationOfRevenueLineItems"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredRevenueCurrent_2f489e06-ec31-46e0-88f1-4451db926233" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DeferredRevenueCurrent"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_DisaggregationOfRevenueLineItems_ba80fc72-3539-4843-8374-688d1f084bc2" xlink:to="loc_us-gaap_DeferredRevenueCurrent_2f489e06-ec31-46e0-88f1-4451db926233" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_GiftCardAndClubORewardsBreakage_b59d92a3-9d2c-4a7d-abc7-7b04ab0d9b45" xlink:href="ostk-20230630.xsd#ostk_GiftCardAndClubORewardsBreakage"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_DisaggregationOfRevenueLineItems_ba80fc72-3539-4843-8374-688d1f084bc2" xlink:to="loc_ostk_GiftCardAndClubORewardsBreakage_b59d92a3-9d2c-4a7d-abc7-7b04ab0d9b45" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisaggregationOfRevenueTable_8d08cb8b-900d-4ea3-9506-fff69edfcd19" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DisaggregationOfRevenueTable"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/all" xlink:from="loc_us-gaap_DisaggregationOfRevenueLineItems_ba80fc72-3539-4843-8374-688d1f084bc2" xlink:to="loc_us-gaap_DisaggregationOfRevenueTable_8d08cb8b-900d-4ea3-9506-fff69edfcd19" xlink:type="arc" order="1" xbrldt:closed="true" xbrldt:contextElement="segment"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredRevenueArrangementTypeAxis_f5039a71-e84d-4056-9016-ef6167d7bf72" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DeferredRevenueArrangementTypeAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_DisaggregationOfRevenueTable_8d08cb8b-900d-4ea3-9506-fff69edfcd19" xlink:to="loc_us-gaap_DeferredRevenueArrangementTypeAxis_f5039a71-e84d-4056-9016-ef6167d7bf72" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredRevenueArrangementTypeDomain_f5039a71-e84d-4056-9016-ef6167d7bf72_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DeferredRevenueArrangementTypeDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_DeferredRevenueArrangementTypeAxis_f5039a71-e84d-4056-9016-ef6167d7bf72" xlink:to="loc_us-gaap_DeferredRevenueArrangementTypeDomain_f5039a71-e84d-4056-9016-ef6167d7bf72_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredRevenueArrangementTypeDomain_bc6af6c4-6798-4cba-989a-be41f60da640" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DeferredRevenueArrangementTypeDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_DeferredRevenueArrangementTypeAxis_f5039a71-e84d-4056-9016-ef6167d7bf72" xlink:to="loc_us-gaap_DeferredRevenueArrangementTypeDomain_bc6af6c4-6798-4cba-989a-be41f60da640" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_ostk_ClubORewardPointsMember_1cfa7878-1fe5-4d42-820c-2adab3972bd8" xlink:href="ostk-20230630.xsd#ostk_ClubORewardPointsMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_DeferredRevenueArrangementTypeDomain_bc6af6c4-6798-4cba-989a-be41f60da640" xlink:to="loc_ostk_ClubORewardPointsMember_1cfa7878-1fe5-4d42-820c-2adab3972bd8" xlink:type="arc" order="0"/>
  </link:definitionLink>
  <link:roleRef roleURI="http://www.overstock.com/role/NETINCOMELOSSPERSHAREAntidilutiveSecuritiesDetails" xlink:type="simple" xlink:href="ostk-20230630.xsd#NETINCOMELOSSPERSHAREAntidilutiveSecuritiesDetails"/>
  <link:definitionLink xlink:role="http://www.overstock.com/role/NETINCOMELOSSPERSHAREAntidilutiveSecuritiesDetails" xlink:type="extended" id="i53f04927d8bf4f588d708035b18eb54e_NETINCOMELOSSPERSHAREAntidilutiveSecuritiesDetails">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems_c0d634f7-748c-4995-804a-0cf15032d0bb" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount_4a245a53-3cd6-4b88-a219-e3eb0c6cbd17" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems_c0d634f7-748c-4995-804a-0cf15032d0bb" xlink:to="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount_4a245a53-3cd6-4b88-a219-e3eb0c6cbd17" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable_5204e00d-7087-4e82-9a10-e198d3254410" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/all" xlink:from="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems_c0d634f7-748c-4995-804a-0cf15032d0bb" xlink:to="loc_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable_5204e00d-7087-4e82-9a10-e198d3254410" xlink:type="arc" order="1" xbrldt:closed="true" xbrldt:contextElement="segment"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis_df36100e-1f3a-42e1-8e15-79ac922ffd54" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/hypercube-dimension" xlink:from="loc_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable_5204e00d-7087-4e82-9a10-e198d3254410" xlink:to="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis_df36100e-1f3a-42e1-8e15-79ac922ffd54" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AntidilutiveSecuritiesNameDomain_df36100e-1f3a-42e1-8e15-79ac922ffd54_default" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AntidilutiveSecuritiesNameDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-default" xlink:from="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis_df36100e-1f3a-42e1-8e15-79ac922ffd54" xlink:to="loc_us-gaap_AntidilutiveSecuritiesNameDomain_df36100e-1f3a-42e1-8e15-79ac922ffd54_default" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AntidilutiveSecuritiesNameDomain_ea35d0aa-2644-4ae9-9588-456e01b75c1f" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AntidilutiveSecuritiesNameDomain"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/dimension-domain" xlink:from="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis_df36100e-1f3a-42e1-8e15-79ac922ffd54" xlink:to="loc_us-gaap_AntidilutiveSecuritiesNameDomain_ea35d0aa-2644-4ae9-9588-456e01b75c1f" xlink:type="arc" order="1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockCompensationPlanMember_5eee57ca-18e7-41e0-bd44-1651d6e41558" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_StockCompensationPlanMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_AntidilutiveSecuritiesNameDomain_ea35d0aa-2644-4ae9-9588-456e01b75c1f" xlink:to="loc_us-gaap_StockCompensationPlanMember_5eee57ca-18e7-41e0-bd44-1651d6e41558" xlink:type="arc" order="0"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeStockMember_19a6fc77-6789-4e5d-bd68-4d1bf9187cd9" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EmployeeStockMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_AntidilutiveSecuritiesNameDomain_ea35d0aa-2644-4ae9-9588-456e01b75c1f" xlink:to="loc_us-gaap_EmployeeStockMember_19a6fc77-6789-4e5d-bd68-4d1bf9187cd9" xlink:type="arc" order="1"/>
  </link:definitionLink>
  <link:roleRef roleURI="http://xbrl.sec.gov/ecd/AwardTypeOnly" xlink:type="simple" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#AwardTypeOnly"/>
  <link:definitionLink xlink:role="http://xbrl.sec.gov/ecd/AwardTypeOnly" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestrictedStockMember" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_RestrictedStockMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:to="loc_us-gaap_RestrictedStockMember" xlink:type="arc" order="4"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeStockMember" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EmployeeStockMember"/>
    <link:definitionArc xlink:arcrole="http://xbrl.org/int/dim/arcrole/domain-member" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:to="loc_us-gaap_EmployeeStockMember" xlink:type="arc" order="5"/>
  </link:definitionLink>
</link:linkbase>
