Oprah Winfrey’s reach truly knows no bounds. As of 2021, the mogul has amassed a net worth of $2.5 billion, according to Forbes, and has built an empire of philanthropy and media production and distribution. Given her many commitments, it makes sense that Winfrey has made homes for herself in numerous cities throughout the United States. Though Montecito, California, has been her main base for more than 20 years, Winfrey has also owned homes in Illinois, Florida, Hawaii, Colorado, and Washington state. She’s also owned, or currently owns, properties in Tennessee and Indiana, though she primarily purchased those residences for family and friends. Here, we’ve rounded up a handful of Winfrey’s real estate holdings, which are an impressive sampling of her eclectic tastes and representation of her various life chapters.
1985
One of Winfrey’s first big real estate ventures was her 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 revealed, but in subsequent years, she snapped up three other units all surrounding the original one, for $1.0625 million, $1.5 million, and $1 million, respectively, according to the Chicago Tribune. Combined, the four units measured 9,625 square feet and featured four bedrooms and five full and two half bathrooms. Winfrey ultimately listed the enormous duplex for $7.75 million in January 2014, and finally sold it for $4.625 million in late 2015.
1994
The Four Seasons Chicago.
Around the same time she was purchasing the last of the four adjacent condos in Water Tower Place, Winfrey also dropped $100,000 on a three-bedroom apartment at the Four Seasons Chicago. The renowned luxury hotel is situated just a few blocks from Lake Michigan and not too far from the Near West Side, where Harpo Studios, Winfrey’s multimedia production company, was located at the time. Winfrey ultimately sold this property for $1.275 million in 2015, the same year she closed the studios for good and relocated to the West Coast.
1995
This year, Winfrey made a much-buzzed-about purchase on exclusive Fisher Island, a 216-acre man-made island situated 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 boasted 20-foot ceilings, and an expansive oceanfront terrace. The unit was located in the high-end Villa Del Mare condominiums, where amenities included a billiards room, a biking trail, multiple swimming pools, and a spa. The residence itself was airy and light-filled, with a wood-burning oven in the kitchen and a spacious main suite with his-and-hers en-suite bathrooms and dressing rooms. Winfrey ended up selling the unit for a then unheard of $6.5 million in 2001 to the former chairman of Campbell’s Soup.
2001
Winfrey began to set down roots for what is now known as the Promised Land, her sprawling home in Montecito, in 2001. The media mogul paid around $50 million for the original 42-acre spread, which included a 23,000-square-foot Georgian-style house, a 6,000-square-foot redwood guesthouse, and an outdoor area perfect for a pool, tennis court, and multiple patios. In the decades following, Winfrey continued to snap up nearby properties to expand her holdings in Montecito; she still calls this sprawling mansion her main home base.
