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Oprah's extensive and continuously evolving real-estate portfolio has garnered heightened attention throughout her life and career, with many prominent industry outlets branding her a "tycoon" regarding her investments which as of 2022, are estimated to total approximately $127 million.
As her talk show was beginning, Oprah first purchased a condominium in Chicago's [[Water Tower Place]] in 1985, before purchasing the condos adjoining and directly below it in 1992, 1993, and 1994, respectively. In 1988, she purchased an 164-acre property including main and guest residences, orchard, and stables in [[Rolling Prairie, Indiana]] as her weekend refuge. In 1992, she purchased an 80-acre compound in [[Telluride, Colorado]], which she would go on to sell in approximately late 2000. In 1994, she also purchased an apartment at the [[Four Seasons Hotel Chicago]]. Between 1996 and 2000 she purchased a total of five condos in different development areas of [[Fisher Island, Florida]]. In 2000, through her Chicago-based LLC Overground Railroad, Oprah purchased her friend [[Gayle King]] an estate in [[Greenwich, Connecticut]]. In 2001, Oprah sold all five of her Fisher Island condos and purchased what would become her "main home base" she has also called "The Promised Land" (where she currently lives as of 2022), a (then) 42-acre (17 ha) estate with ocean and mountain views in [[Montecito, California]].<ref>{{Cite web|url=https://www.chicagotribune.com/news/ct-xpm-2001-04-29-0104290208-story.html|title=Oprah buying 40-acre estate in California|date=April 29, 2001|website=[[Chicago Tribune]]|language=en-US|access-date=November 6, 2022|archive-date=November 6, 2022|archive-url=https://web.archive.org/web/20221106211925/https://www.chicagotribune.com/news/ct-xpm-2001-04-29-0104290208-story.html|url-status=live}}</ref><ref>{{Cite web|url=https://www.realtor.com/news/celebrity-real-estate/oprah-winfrey-impressive-real-estate-portfolio/|title=She Gets a House! And He Gets a House! Oprah Winfrey's Impressive Real Estate Portfolio|date=November 14, 2019|website=[[Realtor.com]]|language=en-US|access-date=November 6, 2022|archive-date=April 16, 2022|archive-url=https://web.archive.org/web/20220416145304/https://www.realtor.com/news/celebrity-real-estate/oprah-winfrey-impressive-real-estate-portfolio/|url-status=live}}</ref>
Additionally that year, she also purchased homes in both [[Elmwood Park, Illinois]] and [[Merrillville, Indiana]] for other family members and friends. Similarly, in 2002, she purchased her father's home in [[Franklin, Tennessee]] and a lakefront condo in [[Milwaukee]], [[Wisconsin]]. In 2003 she listed her compound in Rolling Prairie, Indiana, and sold it in 2004.<ref>{{Cite web|url=https://www.chicagotribune.com/news/ct-xpm-2003-09-14-0309140307-story.html|title=Muhammad Ali, Oprah selling nearby estates|date=September 14, 2003|website=[[Chicago Tribune]]|language=en-US|access-date=November 6, 2022|archive-date=November 6, 2022|archive-url=https://web.archive.org/web/20221106183230/https://www.chicagotribune.com/news/ct-xpm-2003-09-14-0309140307-story.html|url-status=live}}</ref><ref>{{Cite web|url=https://www.upi.com/Entertainment_News/2004/12/16/Oprahs-Indiana-farm-sold-to-developer/39701103246152/|title=Oprah's Indiana farm sold to developer|date=December 16, 2004|website=[[UPI]]|language=en-US|access-date=November 6, 2022|archive-date=March 25, 2016|archive-url=https://web.archive.org/web/20160325220311/http://www.upi.com/Entertainment_News/2004/12/16/Oprahs-Indiana-farm-sold-to-developer/39701103246152|url-status=live}}</ref> From 2003 to 2005, Oprah acquired several properties totaling 163 acres in [[Kula, Hawaii|Kula]] and [[Hana, Hawaii|Hana]], [[Hawaii]] as well as a penthouse apartment in [[Atlanta]], [[Georgia (U.S. state)|Georgia]]. In 2005, she purchased a home in [[Douglasville, Georgia]] which was gifted in 2011 to a family member.
In 2006, Oprah purchased a co-op apartment along [[Lake Shore Drive]] in downtown Chicago, reportedly with plans to permanently move there from her prior adjoined-condo unit in Water Tower Place for the duration of her show but for reasons unknown, the property sat entirely unused until she sold it in 2012.<ref>{{Cite web|url=https://www.chicagotribune.com/real-estate/elite-street/ct-oprah-winfrey-condo-elite-street-1121-biz-20151120-story.html|title=Oprah Winfrey sells Water Tower condo for $4.6 million|date=November 20, 2015|website=[[Chicago Tribune]]|language=en-US|access-date=November 6, 2022|archive-date=November 6, 2022|archive-url=https://web.archive.org/web/20221106145616/https://www.chicagotribune.com/real-estate/elite-street/ct-oprah-winfrey-condo-elite-street-1121-biz-20151120-story.html|url-status=live}}</ref> In 2008, she sold her penthouse apartment in Atlanta. That year, she also listed Gayle King's estate and purchased her (through her second LLC Sophie's Penthouse) a penthouse apartment in midtown [[Manhattan]], [[New York City]] which would later be sold in 2012.
In early 2014, she listed her combined-unit Chicago duplex on the market. Later that year, Oprah came back to [[Telluride, Colorado]] to purchase a 60-acre lot with plans to build on the property. A lawsuit filed against her that year by a retired nuclear physicist living in the area regarding trail access rights was dismissed later that year with the judge citing little case law to support his case, among other issues. The extent of the agreement between all the parties and jurisdictions regarding her subsequent development on the property remains undisclosed.<ref>{{Cite web|url=https://www.telluridenews.com/news/article_19ee2863-83f7-5bad-b0e1-7b08e72b203f.html|title=MV trails case dismissed|date=December 1, 2014|website=[[Telluride Daily Planet]]|language=en-US|access-date=November 6, 2022|archive-date=November 6, 2022|archive-url=https://web.archive.org/web/20221106150355/https://www.telluridenews.com/news/article_19ee2863-83f7-5bad-b0e1-7b08e72b203f.html|url-status=live}}</ref>
In 2015, Oprah purchased another property in Telluride, and later that year, expanded her Montecito compound with another 23-acre estate and yet another 44-acre dedicated crop and equestrian preserve. That year she also sold both of her downtown Chicago homes.
In 2018, Oprah obtained two adjoining parcels of land totaling 23 acres including the Madroneagle compound on [[Orcas Island]], [[Washington (state)|Washington]] and sold her last home property in the Chicago area from Elmwood Park.<ref>{{Cite web|url=https://www.chicagotribune.com/real-estate/elite-street/ct-re-elite-street-oprah-elmwood-park-20181018-story.html|title=Oprah sells final piece of Chicago-area real estate: 4-bedroom Elmwood Park home|date=October 19, 2018|website=[[Chicago Tribune]]|language=en-US|access-date=November 6, 2022|archive-date=November 6, 2022|archive-url=https://web.archive.org/web/20221106183233/https://www.chicagotribune.com/real-estate/elite-street/ct-re-elite-street-oprah-elmwood-park-20181018-story.html|url-status=live}}</ref> In late 2019, Oprah yet again expanded her Montecito home-base compound, this time to 70 contiguous acres, with the purchase of a four-acre complex from actor [[Jeff Bridges]]. In 2021, she sold her Orcas Island compound as she said she was too busy to use it and purchased another compound in Montecito further away from her home-base compound, flipping the latter in 2022 with split properties, one of which was sold to her property manager and longtime personal trainer Bob Greene, and the other to actress [[Jennifer Aniston]].<ref>{{Cite web|url=https://www.architecturaldigest.com/story/oprah-winfrey-real-estate-portfolio|title=Oprah Winfrey's Homes: A Look Inside Her Extensive Real Estate Portfolio|date=October 1, 2021|website=[[Architectural Digest]]|language=en-US|access-date=November 6, 2022|archive-date=November 6, 2022|archive-url=https://web.archive.org/web/20221106145612/https://www.architecturaldigest.com/story/oprah-winfrey-real-estate-portfolio|url-status=live}}</ref><ref>{{Cite web|url=https://www.sheknows.com/living/slideshow/9672/look-inside-oprah-homes/23/|title=A Look Inside 6 of Oprah Winfrey's Homes — Yes, 6|date=November 6, 2019|website=[[SHE Media|She Knows]]|language=en-US|access-date=November 6, 2022|archive-date=November 6, 2022|archive-url=https://web.archive.org/web/20221106145614/https://www.sheknows.com/living/slideshow/9672/look-inside-oprah-homes/23/
===Romantic history===
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