Oprah Earned Wild Praise at the DNC—but Her Multimillion-Dollar Property Portfolio Is Even More Jaw-Dropping

Is there anything Oprah Winfrey can’t do?

On Wednesday night, the billionaire media mogul blew the roof off the Democratic National Convention with a barn burner of a speech.

Clad head-to-toe in purple, the 70-year-old brought the Chicago crowd to their feet with her surprise appearance at the convention.

The self-proclaimed “registered independent” began her rousing address by paying homage to her close ties with the Windy City, having spent years filming her long-running “Oprah Winfrey Show” in the area.

“Who says you can’t go home again?” Winfrey, who is estimated to be worth around $3 billion, according to Forbes, asked the roaring crowd.

The producer of  “The Color Purple” explained in her speech that she’s lived and traveled all over the country.

“I’ve lived in Mississippi, in Tennessee, in Wisconsin, Maryland, Indiana, Florida, Hawaii, Colorado, California, and sweet home Chicago, Illinois,” she told the crowd.

“I have actually traveled this country from the redwood forest—love those redwoods—to the Gulf Stream waters.”

To this day, Winfrey maintains properties across the U.S., including in California, Colorado, Illinois, and Hawaii, having built up an awe-inspiring collection of homes during her many years in the spotlight.

Montecito, CA

Winfrey’s main stateside residence appears to be in the coastal enclave of Montecito, CA, where her neighbors include Prince Harry and Meghan Markle, Gwyneth Paltrow, and Ellen DeGeneres and Portia de Rossi.

In 2001, Winfrey moved to the Central California area with the $50 million purchase of a place she’s dubbed “The Promised Land.” The enormous neo-Georgian estate on 40 acres comprises six bedrooms and 14 bathrooms in 23,000 square feet of living space.

Offering mountain and ocean views, the gorgeous grounds include a pool, stables, landscaped gardens, vegetable gardens, as well as a pond.

Winfrey continues to expand her Montecito masterpiece. She snapped up a neighboring equestrian estate on 23.26 acres in 2015 for $28.85 million.

She also snagged Jeff Bridges’ longtime retreat in Montecito for $6.85 million in late 2019, bringing her total holdings in the area to nearly 70 acres.

In 2021, the savvy investor reportedly picked up a 2-acre estate for $10.8 million and split it in two. She turned around and sold the main farmhouse with mountain and ocean views on an acre to “Friends” star Jennifer Aniston in 2023 for $14.8 million.

Two smaller cottages were sold to her friend and personal trainer Bob Greene for $2.3 million.

Maui, HI

Winfrey also has strong ties to Maui, where she now owns about 1,000 acres.

Her love of the Valley Isle started in 2003, when she purchased two properties in the Kula community, adding up to 23 acres and multiple buildings for $5.3 million. She’s been a part-time resident ever since.

That purchase appears to have included a boutique bed-and-breakfast, perhaps for house guests. One of the quaint homes on the property was featured in O magazine.

Over the following decades, she picked up properties in the area, reportedly spending over $40 million on some 163 acres of prime Hawaiian land.

She didn’t stop there. In March 2023, local news outlet KITV reported that Winfrey had picked up 870 “agriculturally-zoned” acres in Kula for about $6.6 million.

She’s said to have built a secret road to her property, making access to the more populated parts of Maui that much easier (for her).

During the fires that swept through the island in July 2019, local residents called for her to provide her gate code to help with evacuations.

She posted in July 2019, “Access to the road was given to county officials immediately. This was many hours ago. Hoping for the safety of all,” she wrote on X.

Winfrey has also been involved with aiding victims of the 2023 Maui wildfires, donating $10 million and providing assistance at shelter hubs.

In addition to her Kula holdings, she purchased over 60 acres in the Hana area in 2005.

She’s been seen tooling around her property on an ATV.

Telluride, CO

If the media maven tires of sea and sun, there’s always a mountain escape available.

Winfrey purchased 66 acres in coveted Mountain Village, CO, in 2014, for $10,850,000.

She apparently had plans to build a custom home on the property, which sits above the ski town of Telluride.

But while it was being built, she reportedly bought a “temporary” home: 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.

Orcas Island, WA

In 2021, Winfrey pocketed a hefty profit from a purchase she had made years earlier in the Pacific Northwest.

In 2018, the billionaire bought a 40-plus-acre waterfront estate on Orcas Island, WA—part of the San Juan Islands—for $8,275,000.

The secluded four-bedroom compound, nicknamed the “Madroneagle,” comprises two adjoining parcels, which Winfrey reportedly bought in separate transactions. The listing had initially come on the market in 2016 for $12 million, so she scored a serious discount.

The sensational space spans a large, south-facing beach on East Sound and comes with 3,000 feet of waterfront.

In 2021, the property was sold for $14 million in a reported off-market deal. Not a bad return on investment.

Georgia

In 2008, Winfrey let go of a 4,806-square-foot, 39th-floor Atlanta penthouse for $1.8 million. 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.

Chicago, IL

Goodbye, Chicago! “The Oprah Winfrey Show” broadcast from Chicago from 1986 to 2011. And along the way, Winfrey scored a few properties in Illinois. Winfrey appears to have moved on from her real estate there after the show ended.

In the 1990s, she bought four condos on the 56th and 57th floors of a luxury high-rise. She later sold the combined 9,600-square-foot property 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 unit was sold for $1,275,000 in 2015.

She unloaded three units in a historic downtown building known as Acorn Lofts: In 2013, she sold one of the live-work spaces for $675,000, another for $507,000, and the third for $875,000.

She also sold a modest Colonial in Elmwood Park, IL, for $375,000 in 2018.

Florida

In the late 1990s, Winfrey tried out Florida life. She spent time at 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 2000s. 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 was sold in 2001 for $6.5 million. At the time, the sale price was considered “unheard of.” These days, that’s the median home price on the exclusive island escape.

Spreading the love

Winfrey likes to spread the real estate love: 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.