Oprah Winfrey’s Homes: An Overview of Her Extensive Real Estate Portfolio


Oprah Winfrey’s reach really knows no bounds. In 2021, the mogul amassed a net worth of $ 2.5 billion, according to Forbes, and built an empire of philanthropy and media production and distribution. Considering her many engagements, it makes sense that Winfrey would have settled in many cities across the United States. Although Montecito, California has been its main base for over 20 years, Winfrey has also owned homes in Illinois, Florida, Hawaii, Colorado, and Washington state. She also owns, or currently owns, properties in Tennessee and Indiana, although she has primarily purchased these residences for her family and friends. Here, we’ve rounded up a handful of Winfrey’s real estate, which is an impressive sample of his eclectic tastes and portrayal of his various chapters in life.


One of Winfrey’s first big real estate ventures was his purchase of a condo in Chicago’s prominent Water Tower Place, located along the city’s Magnificent Mile. The original purchase price was never publicly disclosed, but over the following years it purchased three more units, all surrounding the original unit, for $ 1.0625 million, 1.5 million dollars and $ 1 million, respectively, depending on the Chicago Tribune. Together, the four units measured 9,625 square feet and had four bedrooms and five full bathrooms and two powder rooms. Winfrey finally listed the massive duplex for $ 7.75 million in January 2014, and ultimately sold it for $ 4.625 million in late 2015.


The four seasons of Chicago.

Photo: Christian Horan Photography

Around the same time she was buying the last of four adjacent condos at Water Tower Place, Winfrey also gave up $ 100,000 for a three-bedroom apartment at the Four Seasons Chicago. The famous luxury hotel is located a few blocks from Lake Michigan and not far from the Near West Side, home to Harpo Studios, Winfrey’s multimedia production company at the time. Winfrey eventually sold this property for $ 1.275 million in 2015, the same year she closed the studios permanently and moved to the West Coast.


This year, Winfrey made a popular purchase on the exclusive Fisher Island, a 216-acre man-made island just off the coast of Miami. She paid an undisclosed amount for a four-bedroom, six-bathroom penthouse condo, which measured 6,170 square feet and had 20-foot ceilings and an expansive oceanfront deck. The unit was located in the upscale Villa Del Mare condominiums, where amenities included a billiard room, bike path, multiple pools, and a spa. The residence itself was airy and bright, with a wood-burning oven in the kitchen and a spacious master suite with bathrooms and walk-in closets for him and her. Winfrey ended up selling the unit for a then unseen amount of $ 6.5 million in 2001 to the former president of Campbell’s Soup.


Winfrey began to take root for what is now known as the Promised Land, his sprawling home in Montecito, in 2001. The media mogul paid around $ 50 million for the original 42-acre expanse, which comprised an area of ​​23,000 square feet. Georgian style house, 6,000 square foot redwood guesthouse and outdoor space perfect for a swimming pool, tennis court and several patios. Over the following decades, Winfrey continued to take over neighboring properties to expand his holdings in Montecito; she still calls this sprawling mansion her main home base.

That same year, Winfrey also bought a much more modest four-bedroom Colonial-style home in the suburb of Elmwood Park, just outside of Chicago, for $ 298,000. The TV personality invested money in updating the roof and gutter system, garage door, and heating and air conditioning system, but left the 2,250 square foot home as is. . It eventually sold for $ 375,000 in 2018, leaving her with no more properties in Chicago.


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