3. Maui, Hawaii
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.
Instead of condos, she kept the 163 acres mostly untouched, but renovated the property's enormous farmhouse to build an island getaway for herself.
Every detail of the home, from the wraparound veranda to the French doors and hand-embroidered curtains, adds to the incredible atmosphere.
The Maui estate is also the site of Oprah's Farm, where she harvests her own fruits and vegetables.
Despite the giant size, Oprah considers this her "small home," and says it's perfect for entertaining in groups of two or three.
While Oprah's is deeply linked to the city where her career began, she recently sold off all of her property in Chicago.
Along with a $4 million duplex and a $2.8 million co-op, Oprah owned this (relatively) small 2,250 square foot residential property.
She purchased the 1941 brick home, which has four bedrooms and two bathrooms, in 2001, but never actually lived there.
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
If her Chicago home was down-to-earth, then Oprah's ski chalet is a true billionaire property.
Oprah snapped it up in 2015 for $14 million, and while that's a hefty price tag, the location is undeniably great.
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.
But the best feature is down in the basement: a 1,600 bottle wine cellar designed to look like an abandoned mine shaft.
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?
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