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Take A Look Inside Oprah's 5 Most Luxurious Homes

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O Magazine

3. Maui, Hawaii

O Magazine
O Magazine

Oprah's property manager and former personal trainer Bob Greene convinced her to buy the property next to his in Maui, to keep it from being turned into condos.

O Magazine
O Magazine

Instead of condos, she kept the 163 acres mostly untouched, but renovated the property's enormous farmhouse to build an island getaway for herself.

O Magazine

Every detail of the home, from the wraparound veranda to the French doors and hand-embroidered curtains, adds to the incredible atmosphere.

O Magazine

The Maui estate is also the site of Oprah's Farm, where she harvests her own fruits and vegetables.

O Magazine

Despite the giant size, Oprah considers this her "small home," and says it's perfect for entertaining in groups of two or three.

4. Chicago

Trulia

While Oprah's is deeply linked to the city where her career began, she recently sold off all of her property in Chicago.

Trulia

Along with a $4 million duplex and a $2.8 million co-op, Oprah owned this (relatively) small 2,250 square foot residential property.

Trulia
Trulia
Trulia

She purchased the 1941 brick home, which has four bedrooms and two bathrooms, in 2001, but never actually lived there.

Trulia

It went on the market earlier this year for a very reasonable $393,875, so if you're in the market for a family home in Chicago, this could be a steal.

5. Telluride, Colorado

Joshua Johnson Photography

If her Chicago home was down-to-earth, then Oprah's ski chalet is a true billionaire property.

Joshua Johnson Photography

Oprah snapped it up in 2015 for $14 million, and while that's a hefty price tag, the location is undeniably great.

Joshua Johnson Photography

Before you even step inside the 8,700 square foot mountain mansion, you'll notice the heated driveways and a three-car garage.

But there's also a sauna, indoor hot tub, chef's kitchen, six decks, a theater, a guest house, and a fire pit that's suspended in the treetops.

Joshua Johnson Photography
Joshua Johnson Photography
Joshua Johnson Photography
Joshua Johnson Photography
Joshua Johnson Photography
Joshua Johnson Photography

But the best feature is down in the basement: a 1,600 bottle wine cellar designed to look like an abandoned mine shaft.

Joshua Johnson Photography

Four people can sit inside a fake mine cart and ride to a nearby ski trail without ever stepping outside. How's that for added value?

Share this list and tell us which home was your favorite!

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