Oprah Winfrey, the billionaire media mogul, philanthropist, and actress, also happens to be a real estate tycoon.
Over the years, we’ve covered the media queen as she’s bought and sold some of her many properties. But we did some digging, and it turns out, those were just the tip of the iceberg of Winfrey’s holdings.
When it comes to real estate, Winfrey has so many favorite things. The result is a massive property portfolio. Let’s break down the list of homes she’s bought, sold, and currently holds.
‘The Promised Land’
Although she owns homes from coast to coast, Winfrey’s main residence can be found in Montecito, CA, a coastal community near Santa Barbara. It’s nearly two hours (with traffic!) northwest of Hollywood.
To get a sense of just how exclusive Montecito is, the median list price of a home in the tony town is $2.3 million, and it has a couple of dozen homes currently on the market whose asking prices are over $10 million.
In 2001, Winfrey moved into the neighborhood with the $50 million purchase of a place she’s dubbed “The Promised Land.” The enormous Neo-Georgian estate comprises six bedrooms, 14 bathrooms, and 23,000 square feet on 40 acres.
Offering mountain and ocean views, the gorgeous grounds include a pool, stables, landscaped gardens, her bountiful vegetable gardens, as well as a pond.
Winfrey continues to expand her Montecito masterpiece. She snapped up an additional 23.26 acres in 2015 for $28.85 million.
Most recently, she snagged her neighbor Jeff Bridges’ longtime retreat for $6.85 million, bringing her total acreage in the area to nearly 70 acres.
Aloha, Hawaii!
Winfrey’s romance with the island of Maui started back in 2003, when she purchased two properties in the Kula community on the Valley Isle, adding up to 23 acres for $5.3 million. Each of those lots contain multiple buildings.
That purchase appears to have included a boutique bed and breakfast. So it seems she always expected to welcome guests to her tropical paradise. In fact, one of the redone homes on her land was featured in O Magazine.
Since then, the queen has continued snatching up properties in the area, for a total of over $40 million and some 163 acres, according to O Magazine, which featured this video of Winfrey herself tooling around her property on one of two all-terrain vehicles given to her by Ralph Lauren. (She discovered the ATVs on his ranch, she tells the magazine.)
She’s even rumored to have built a secret road to her property, making access to the more populated parts of Maui that much easier.
In addition to her Kula holdings, she purchased over 60 acres in the Hana area back in 2005.
The Winfrey (Windy) City
“The Oprah Winfrey Show” was broadcast from Chicago from 1986 to 2011. And along the way, Winfrey scored a few properties in Illinois. But with the end of her show’s long run in the Windy City, Winfrey appears to have also moved on from her real estate there.
In the 1990s, she bought four condos on the 56th and 57th floors of a luxury high-rise, with the idea of converting them into one duplex. The 9,600-square-foot property sold in 2015 for $4.6 million.
She also shed a three-bedroom apartment over the Four Seasons Hotel that she had bought in 1994 for $100,000. The high-end home sold for $1.275 million in 2015.
She also bid adieu to three units in a historic downtown building known as Acorn Lofts. In 2013, she sold three of the live/work spaces, one for $675,000, another for $507,000, and a third for $875,000. For an idea of what the lofts look like, there’s a unit currently on the market (not connected to Winfrey!) for $1.6 million.
She also sold a modest Colonial in Elmwood Park, IL, for $375,000 in 2018.
Although we also spotted homes she’d picked up in Tennessee, Illinois, and Indiana, most of those houses are believed to be occupied by members of her family .
Mountain getaway
Oprah also has a cold-weather hideaway. She purchased 66 acres in coveted Mountain Village, CO, in 2014, for $10,850,000.
She apparently had a custom home constructed on the property, which sits above the ski town of Telluride. But while it was being built, she reportedly bought a “temporary” home away from home to monitor the construction: a high-tech mansion in Telluride for $13.7 million.
The contemporary construction offers complete privacy and direct trail access. The grounds include a treetop observation tower, a funicular, and a glass and steel bridge over the great room.
Georgia on her mind
Some long-ago purchases in this Southern state have since been sold by the 65-year-old. In Atlanta, Winfrey sold a 4,806-square-foot, 39th-floor penthouse for $1.8 million in 2008. Reports were not clear on whether she ever made use of the place for herself. She made a small profit on the property, which she bought in 2003 for $1,515,000.
She also had a 6,000-square-foot house in Douglasville, GA, on 1.6 acres, which she had bought in 2005 for $825,000. That suburban five-bedroom home was gifted to a lucky somebody in 2011.
Island living
Back in the late 1990’s, Oprah had a fling with Florida life. She decamped to ultra-exclusive Fisher Island as a winter escape and snapped up multiple condos on the private island paradise, which is known as having one of the highest per capita incomes in the country.
However, she’s since let go of her Florida homes, which were all sold in the early 2000’s. Many of them were smaller one-to-four bedroom apartments, and appeared to be for her entourage and friends.
Her 6,170-square-foot penthouse sold in 2001 for $6.5 million. At the time, the sale price was considered “unheard of.” That seems quaint now—the same penthouse recently changed hands again for $13.5 million.
Of course, after those sales, Oprah began buying up homes in Hawaii, a place that obviously held more appeal for the A-Lister.
And the island life beckons closer to the mainland, too. The real estate maven reportedly picked up a 43-acre estate on Orcas’ Island, part of the San Juan Islands in Washington state, last May. Oprah’s new digs, for which she paid $8.2 million, include a four-bedroom, five-bathroom compound, plus a guesthouse.
