10 Most Ridiculously Rich Things Oprah Owns (And Yes, They’re Real)
When your name is Oprah Winfrey, shopping means buying the private jet—not boarding it. From sprawling estates to eye-popping art sales, her taste is as elevated as her bank balance. But it’s not just about price tags. Oprah’s purchases reflect a life built on power, influence, and carefully chosen indulgence.
Whether she’s gifting homes to loved ones or flying above the clouds in custom interiors, every item on this list tells a story of success—and serious spending. These aren’t just rich-person buys; they’re billion-dollar lifestyle choices that make even moguls pause. Let’s peek inside the empire, because being a billionaire should look like this.
The Promised Land – $88 Million
Credit: Instagram
Her crown jewel is this 42-acre Montecito estate in California. With six bedrooms, 14 bathrooms, and an artificial lake, it’s more than a home—it’s a self-contained kingdom. Named after a dream Martin Luther King Jr. once spoke of, the property blends grandeur with soul.
Gulfstream G650 Jet – $70 Million
Credit: Instagram
Oprah’s private jet isn’t just luxurious—it’s top-tier even by billionaire standards. This twin-engine aircraft has a personalized interior and offers an intercontinental range with maximum comfort. It’s the sky-high version of flying first, last, and only class.
Antigua Getaway – Estimated $28 Million
Credit: Instagram
Located on the Caribbean island of Antigua, this coastal compound offers sweeping ocean views and all the tropical seclusion anyone could want. Hidden behind walls and swaying palms, it’s built for privacy, leisure, and hosting A-list friends far from paparazzi lenses.
Telluride Ski Lodge – Undisclosed Value
Credit: Instagram
Set in the Colorado Rockies, this 8,700-square-foot alpine retreat includes a faux mining cart that connects to a ski trail, a 1,600-bottle wine cellar, and a suspended forest walkway. Add a sauna and seven-person hot tub, and it’s an après-ski fantasy.
Maui Mountain Estate – Estimated $60 Million
Credit: Instagram
Perched on the slopes of Haleakalā in Kula, Oprah turned a humble gray farmhouse into a chic sanctuary. Initially bought for $5.3 million in 2003, the estate now spans over 1,000 acres. It’s both a personal retreat and a conservation effort.
Klimt Art Sale – $150 Million
Credit: Instagram
In one of the art world’s biggest private deals, Oprah sold Gustav Klimt’s Portrait of Adele Bloch-Bauer II to a Chinese buyer for $150 million in 2016. She had bought the piece for $87.9 million just a decade earlier—proof that her eye is as valuable as her wallet.
Streeterville Condo, Chicago – $5.6 Million
Credit: Instagram
Though she never lived here, this 5,000-square-foot residence had a solarium, butler’s pantry, and formal dining room. She leased it out for $15,000 a month, turning luxury into passive income in the Windy City.
Manhattan Penthouse – $8 Million
Credit: Instagram
On the 36th floor of Place 57 in Midtown, Oprah’s three-bedroom penthouse had all the trappings: a power shower, three walk-in closets, and a 700-foot private terrace. This Manhattan sky-high escape offered views as impressive as the guest list.
Water Tower Place Condo – $4.6 Million
Credit: Instagram
Once her primary Chicago residence, this expansive condo was pieced together from four units. The result? Over 9,600 square feet of spiraling staircases, two kitchens, and lakefront views made it a high-rise palace.
Fisher Island Condo – $1.1 Million
Credit: Instagram
Sold in 2008, this Miami Beach property was a masterclass in tropical luxury. Think glass walls, breezy ocean views, and a layout to make every room feel like a resort suite.
Douglasville Home for Half-Sister – $600,000
Credit: Instagram
After reconnecting with her half-sister Patricia Lofton in 2010, Oprah gifted her this quiet Georgia home. Set on nearly a third of an acre, the house is modest by billionaire standards but rich in significance.
Bombardier Global Express – Estimated $42 Million
Credit: Instagram
Yes, she has another jet. The Bombardier Global Express reportedly includes an onboard shower and ultra-quiet cabin design. It’s a second sanctuary in the sky, proving Oprah doesn’t do “just one” of anything.
Lavish Furniture Auction – Millions Raised
Credit: Instagram
In 2015, Oprah auctioned more than 500 pieces of European art, antiques, and memorabilia, including gilded mirrors, crystal, and fine French furniture. Proceeds went to her leadership academy in South Africa, making this a philanthropic power move.
Telluride Wine Cellar – Included in Estate
Credit: Instagram
Built into her Colorado hideaway, this wine lover’s dream can hold 1,600 bottles. It’s climate-controlled and private—ideal for quiet nights, a post-slope toast with select friends, and a sommelier-worthy selection.
Private Tea House – Included in Montecito Estate
Credit: Instagram
Tucked into her Montecito property, the tea house is a serene escape for meditation and reflection. It’s where Oprah reportedly reads, hosts intimate guests, and decompresses—proof that luxury and tranquility aren’t mutually exclusive.