From Mansions To The DNC: Oprah's Influence Extends Beyond Real Estate

Oprah Winfrey captivated the audience at the Democratic National Convention in Chicago last week with a powerful speech.

Dressed in all purple, the billionaire media icon surprised the Chicago crowd and brought them to their feet. The 70-year-old self-described "registered independent" opened her inspiring address by honoring her deep connection to the Windy City, where she spent years hosting the iconic "Oprah Winfrey Show."

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"Who says you can't go home again?" Winfrey asked the cheering crowd.

The 70-year-old producer of "The Color Purple" said she's lived and traveled nationwide.

"I've lived in Mississippi, Tennessee, Wisconsin, Maryland, Indiana, Florida, Hawaii, Colorado, California and sweet home Chicago, Illinois," she told the audience.

According to Realtor.com, Winfrey continues to own real estate across the United States, including in California, Colorado, Illinois and Hawaii.

Realtor.com took a look at Winfrey's real estate holdings. Here's what it found:

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Montecito, California

Winfrey's primary residence is in the coastal community of Montecito, California, where she counts Prince Harry and Meghan Markle, Gwyneth Paltrow, Ellen DeGeneres and Portia Rossi among her neighbors.

In 2001, Winfrey moved to the Central California area and purchased an estate she named The Promised Land for $50 million. The 40-acre neo-Georgian property features a 23,000-square-foot mansion with six bedrooms and 14 bathrooms. The estate offers stunning mountain and ocean views along with beautifully landscaped gardens, a pool, stables, vegetable gardens and a pond.

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Winfrey has continued expanding her Montecito retreat over the years, acquiring a neighboring 23.26-acre equestrian estate for $28.85 million in 2015 and purchasing Jeff Bridges' property for $6.85 million in 2019.

In 2021, she bought a 2-acre estate for $10.8 million and later divided it into two parcels. In 2023, she sold the main farmhouse to "Friends" star Jennifer Aniston for $14.8 million and the remaining two cottages to her friend and personal trainer Bob Green for $2.3 million.

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Maui, Hawaii

Winfrey also has deep connections to Maui, Hawaii, where she owns about 1,000 acres.

Her love affair with Valley Isle began in 2003, when she bought two properties in the Kula area totaling 23 acres with multiple buildings for $5.3 million.

Over the years, Winfrey continued acquiring land in the area, reportedly spending more than $40 million to amass about 163 acres of prime Hawaiian real estate. In March 2023, local news outlet KITV reported that she purchased 870 acres of agricultural land in Kula for around $6.6 million.

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Telluride, Colorado

When the media mogul wants a change from the sea and sun, she can retreat to her mountain getaway perched above the ski town of Telluride, Colorado. Winfrey purchased 66 acres in Mountain Village for $10.85 million in 2014.

While awaiting construction, she acquired a "temporary" home: a high-tech mansion in Telluride for $13.7 million.

The modern estate offers total privacy with direct trail access. Its features include a treetop observation tower, a funicular and a striking glass-and-steel bridge spanning the great room.

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Orcas Island, Washington

In 2021, Winfrey secured a significant profit from a Pacific Northwest property she had purchased years earlier.

In 2018, the billionaire acquired a 40-plus-acre waterfront estate on Orcas Island, Washington – part of the San Juan Islands – for $8.3 million. The secluded four-bedroom compound, Madroneagle, consists of two adjacent parcels Winfrey reportedly purchased in separate transactions.

Winfrey sold the estate for $14 million in an off-market deal in 2021.

Winfrey also owned property in Georgia, Chicago, and Florida, but she appears to have sold those. She purchased homes in Tennessee, Illinois, and Indiana, which are thought to be occupied by her family members.

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