The Mesmerizing Homes Of Oprah Winfrey- Lovely All Around

A-lister homes are hard to track the way they get bored of their real estate and move on so quickly. As for the many homes of Oprah Winfrey, these aren’t easy to keep track of either, but at least she keeps them long enough to get a story out before it becomes yesterday’s news.

Here are 6 homes that Oprah Winfrey keeps in the books, each one as lovely as the next.

Madroneagle – Orcas Island, Washington

This 43-acre estate proudly carries almost 10,000 square feet of home with 3,000 feet of private shoreline, making this one of the more scenic homes of Oprah Winfrey.

orcas island house exterior at dusk

In fact, San Juan County where this is located has more miles of shoreline (375 miles) than any other single county in the United States.

orcas island shoreline
Inside of Oprah Winfrey's home-living area
Windermere Real Estate

With reclaimed timber throughout the home, the house had a warm rustic feeling encompassing the 4-bedroom, 3.5-bath residence with a wine cellar and tasting room down below.

The house also has a workshop and a guest house, along with a mooring buoy nearby. Not surprising as Orcas Island is the largest of the San Juan Islands of the Pacific Northwest with plenty going on in the water.

oprah winfrey house interior living room

Here we’re sure Oprah enjoys the views of orcas, minke whales, harbor seals, bald eagles, and great blue herons.

It’s kind of like an entertainment park, although the admission for this waterfront view hits US$8.75 million. Certainly makes the cost of admission at SeaWorld look like a bargain now.

killer whale breaching at orcas island

These San Juan Islands attract billionaires and celebrities, including Bill Gates, Chris Pratt, and the Nordstrom family. With an average of 247 days of sunshine each year, flip-flops never go out of style for these celebs.

Promised Land Estate – Montecito, California

When it comes to the homes of Oprah Winfrey, this one doesn’t hold back. This tranquil 42-acre property was acquired for US$52 million in 2001, but what a difference a day makes.

Fast forward, we’re looking at a value of US$100 million for this 23,000-square-foot neo-Georgian-style mansion.

Oprah Winfreys montecito mansion from above

We’ve spoken of Stedman Graham, Oprah’s longtime companion confined to the guest house, but with several living rooms, a library, a kitchen, two home theatres, a wine cellar, an office, six bedrooms, and 14 bathrooms it is not a stretch to think he’s now allowed inside.

Homes of Oprah Winfrey orcas island
Windermere Real Estate

Hard to imagine any complaints from the Stedman arena anyway, seeing that the guest house is a whopping 4,000 square feet. Regardless, the buildings on these grounds make this one of the more grandiose homes of Oprah Winfrey.

Since her purchase, this estate now spans about 70 acres. We call that a makeover, celebrity style.

Hawaiian Hideaway – Oprah Winfrey’s Maui Estate

Located on the Hawaiian island of Maui, this lovely farmhouse homestead covers around 23.7 acres of tropical paradise.

Maui house exterior
Photo by Michel Arnaud

Oprah has reportedly bought up a total of US$60 million worth of land and buildings (now expanded to 163 acres of land) in the area making this a bit more than your typical vacation home.

oprah oprah winfreys hawaiian home
Photo by Michel Arnaud

The wrap-around veranda offers spectacular views of the surrounding mountain vistas and ocean and she also runs a bed and breakfast on the site, where she grows fruit, vegetables, and flowers. A well-rounded lifestyle for paradise living!

Contemporary Ski Chalet – Telluride, Colorado

Switching gears from a summertime vacation home to winter weather fun, Oprah bought this 8,700-square-foot property back in 2014 for US$14 million on 60 acres of mountainous terrain.

Many homes of oprah winfrey telluride
Telluride interior
Joshua Johnson Photography

This five-bedroom and 6.5-bathroom chalet come with a huge stone fireplace as the centerpiece surrounded by floor-to-ceiling windows. Needless to say, this dramatic interior doesn’t hold back.

Joshua Johnson Photography

Her wine cellar is more like a wine tunnel, extending 55 feet and holding 1,600 bottles of wine. The wine cellar was designed to simulate the feeling of exploring an old historical mining tunnel, complete with water mists, and sound effects.

oprah winfreys wine cellar
telluride kitchen in many homes of oprah winfrey
Joshua Johnson Photography

Adding a library and to-die-for kitchen with exposed steel beams, custom wood cabinetry, and stone walls makes this a formidable winter getaway. It’s also a techy’s dream.

Along with a tempered glass bridge with an integrated fiber optic lighting system connecting a private office to the master suite, the driveway is also heated to stave off any snowfall. Hey, Oprah is an avid skier, and nothing’s gonna stop her from hitting the slopes.

Telluride is no stranger to the rich and famous, with a typical home value exceeding US$1 million. Other neighbors, past and present have included Tom Cruise, Kevin Costner, and Jessica Beal.

Not too far away from our top Aspen ski lodges where other A-listers are known to frolic – these celebs’ ski lodges hop like college kids bar hop.

Seamair Farm – Montecito, California

Oprah expanded her Montecito holdings by purchasing a 23-acre equestrian estate for US$28.9 million. Somewhat modest as a single-story ranch house, this is nonetheless a mid-century pedigree home designed by famed architect Cliff May.

Seamair farm home
seamair farm estate
Sage Auctions/Lands of America

Inside, there’s the open floor plan that’s typical of mid-century mastery and 4 bedrooms, 5.5 bathrooms, a wine cellar, and four fireplaces.

The estate’s equestrian facilities consist of well-manicured lawns surrounding riding rings, perfectly maintained stables, and a 2-acre avocado grove, which to us makes any price tag on this property worthwhile.

riding arena at oprahs homes
Sage Auctions/Lands of America

Another Montecito Home – Montecito, California

Understanding the unique location of this additional Spanish Revival Montecito home, helps us understand why she acquired this property in 2019.

montecito spanish home
Montecito estate
Coldwell Banker

The former Jeff Bridges home sits right between her other Montecito home and Seamair farm.

Our best guess is she no longer has to hear some grumpy old guy yelling “Get off my lawn” when cutting over from one property to another. Our other best guess is that this ties up the lots quite nicely, completing a fabulous Montecito portfolio.

montecito stables
Coldwell Banker

Purchased for a mere US$6.85 million, there’s some serious prime land value here, coming in at 4 acres.

The home also has the standard luxe items you’d expect in a pricey Santa Barbara adjacent community – stables, tack room, guest house, and pool. Another fine addition to the homes of Oprah Winfrey!


There have been 4 other houses Oprah Winfrey has owned and sold since 2012, which include her primary home in Chicago, and other Chicago area properties in downtown and the Gold Coast neighborhood.

Oprah also bought her long-lost half-sister a home for US$500,000 in Wisconsin, but we’re calling that her sister’s home.

We already know Oprah Winfrey is one of the most generous celebrity givers on the planet, so who really knows who else she’s bought for?

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