Oprah Winfrey's Many Multimillion-Dollar Homes, From Chicago to Maui and Everywhere in Between

Media mogul is worth an estimated $3.1 billion, so it's no wonder her real estate portfolio is the stuff dreams are made of!

By Rebecca Macatee Aug 22, 2016 7:00 PMTags

In order to live your best life, you've got to love the place you call home—or in Oprah Winfrey's case, the multimillion dollar homes you own all over the country. 

It should come as no surprise to anyone that the media mogul's real estate portfolio is the stuff of dreams. According to Forbes, she's got a net worth of around 3.1 billion (yes, with a B), so dropping $28 million on a horse farm barely even puts a dent in Queen O's wallet. 

Earlier this year, Oprah purchased the Seamair Farm Estate, a 23-acre horse farm in Montecito. The "once in a lifetime property" hadn't been on the market in over 30 years, so Oprah was lucky to purchase the lavish property at auction. 

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This particular home features four bedrooms, five bathrooms, a swimming pool, plenty of space to garden and a filled fish pond. Although the property is equipped with everything a modern equestrian could need, E! News learned that Oprah didn't want the horses and they were not included in her purchase of the home and its land.


This, of course, isn't the first home in the area owned by O. According to Curbed, she purchased a 23,000-square-foot home also in Montecito for a reported $50 million back in 2004. The home was lavish and lovely, for sure, but it wasn't Oprah, so in 2013, she gave it a make-under and let O magazine readers in on the process.

"I knew my house was impressive," she wrote. "I mean, just about every guest I ever invited for dinner told me so as they perched on the edge of the opulent sofa, trying not to get fingerprints on anything. I owned a stately home and I poured my heart and soul into making it perfect."

Perfect wasn't right, though, so Oprah enlisted the help of designer Rose Tarlow, who told the media mogul, "This house has nothing to do with you." From there, Oprah changed the decor of the home to one that was more "true to myself," explaining in O, "All I can tell you is that I'm evolving, my taste is, too, and someday soon this room will represent the person I've become."

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When Oprah wants to relax but wants a change of pace from California, she can take a private jet on over to her sprawling estate in Maui! 

According to Forbes, Oprah owns a whopping 163 acres of property in the idyllic Hana area. Nestled neatly upon this pricy piece of land is the renovated, 21st-century farmhouse Oprah featured in O magazine a few years back. She worked with a decorator named Ellie, who said the media mogul liked the Hawaiian home's "small scale."

"She already has a large home in Santa Barbara—this seems to go back to something real and personal," Ellie told O magazine. "It's a great house for her and two or three friends."

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Oprah has another vacation home back in the continental U.S. in Telluride, Colo. According to the Wall Street Journal, she purchased a fully furnished, five-bedroom home in 2015 for an estimated $14 million. The 8700-square-foot mountain mansion features an extravagant wine cellar, six decks and—brace yourself—a treetop fire pit. (Told you Oprah was living her best life!)

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A good portion of O's pre-OWN financial success came from her work based in Chicago. The Windy City was home to The Oprah Winfrey Show from 1986 to 2011. She first purchased a unit in Water Tower Palace back in 1985, according to the Chicago Tribune. By 1992, she purchased an adjoining unit for just over $1 million and then another adjoining unit for $1.5 million the next year. According to the Chicago Tribune, Oprah "rounded out her purchases in 1994" when she paid $1 million for another adjoining unit.

It wasn't until 2015 that Oprah sold her 9,625-square foot Chicago home for a reported $4.625 million.

Not bad, huh? Keep in mind, too, these are just the homes Oprah's purchased in her own name. There's no telling what else this land-loving superstar owns under pseudonyms and private trusts! It's enough to inspire us all to get to work on our own empires!

—Reporting by Bobby Caruso, Sara Kitnick & Holly Passalaqua

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