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Oprah Winfrey’s Amazing Real Estate Across The Country

June 6, 2025
in Entertainment, News
Reading Time: 7 mins read
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There’s a reason why they call Oprah Winfrey the “Queen of All Media.” The Emmy award-winning talk show host successfully launched her own television network, magazine and production company. And we can’t forget Oprah’s Book Club which has helped propel Black authors like Colson Whitehead and Tayari Jones into the spotlight.

All of those boss moves have helped her amass a net worth of over $3 billion and a pretty impressive real estate portfolio worth over $100 million. Although Winfrey keeps her guest lists pretty exclusive, we were able to check out some of the places she’s called home over the years.

Take a peek inside some of Oprah Winfrey’s amazing homes.

Chicago Condos

YouTube/ABC 7 Chicago

While taping “The Oprah Winfrey Show” in Chicago, Winfrey purchased four units inside the iconic Water Tower Place on Chicago’s Magnificent Mile.

A Duplex to Die For

ABC13.com

Winfrey combined the four apartments to make a luxurious 9,000 square-foot duplex, complete with four bedrooms, five full bathrooms and two half baths.

Spa-Like Space

ABC13.com

The condo is full of high-end features, including this spa-like bathroom with a deep soaking tub.

The Promised Land

YouTube.com

In 2001, Oprah Winfrey began setting up the ultimate retreat on over 40 acres of land in Montecito, California. The heart of the property, which she calls “The Promised Land is the main house – a stunning 23,000 square-foot Georgian home that is fit for a media queen.

A Reading Room

YouTube.com

It’s only natural that a book-lover like Winfrey would have a cozy reading room with floor-to-ceiling shelves to hold all of her favorite reads.

Lots of Living Rooms

YouTube.com

The home features several living spaces that allow her guests to relax and enjoy conversation – and the eye-catching artwork.

Dining Room

YouTube.com

The spacious dining room is made for dinner parties for Oprah and her special guests. Oh, to be a fly on the wall to hear the conversations that go down here!

Spilling the Tea

YouTube.com

The home features a tea house, a bright, airy room perfect for enjoying a quiet cup while taking in the garden view.

The Guest House

YouTube.com

Although the main house is spacious, the property also includes a 5,000 square-foot guest house with a pool and plenty of lush greenery.

Even the Horses Have a Nice Home

YouTube.com

With all of those acres, there is plenty of room for horses, which is why Winfrey’s property includes private stables.

Telluride Mansion

YouTube.com

In 2014, Winfrey bought an 8,000 square foot mansion in historic Telluride, Colorado. The secluded woodsy home has five bedrooms and six-and-a-half bathrooms.

A Cozy Cabin

YouTube.com

Once inside the home, you’ll be wowed by all of the stone and wooden accents, which give a cozy cabin vibe.

Mountain Views

When you have a picture-perfect view of the Rocky Mountains like this one, floor-to-ceiling windows are a must.

Made for Relaxing

YouTube.com

Every detail of this home is made for relaxing, including this jacuzzi tub that allows Oprah and her guests to take in the beautiful nature view.

Straight From The Root

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