- Oprah sold her Orcas Island estate in 2021 for $14 mil.
- Oprah offloaded one of her Montecito estates to actress, Jennifer Aniston, for $14.75 in 2022.
- Oprah sold an additional ranch-style estate in Montecito in 2023 for $14.23.
- Oprah’s net worth currently sits at a whopping $2.5 billion as of 2023.
The Queen of TV. The giver of gifts. The icon the entire world has been influenced by. Oprah! Though her childhood was laced with poverty and abuse, Lady O has beaten the odds and become one of the most famous, influential, and wealthiest women in the universe. Oprah has homes from coast to coast and her real estate portfolio is always growing. There isn’t just one Oprah house. Oprah Winfrey house portfolio is only expanding!
Where Does Oprah Live?
So, how many houses does Oprah own? Again, there isn’t just one Oprah Winfrey house. In fact, the major superstar has houses all over the United States, at least 8 of them.
Where does Oprah have homes? She has multiple houses located in Montecito, California, and another in Maui, Hawaii for when she wishes to escape the fast-paced Californian lifestyle. Her main home, however, is one of the two Montecito mansions where she spends the majority of her time. See more on Oprah house below!
Oprah House Montecito, CA (Current)
Where does Oprah live now? Exactly where does Oprah live in Montecito, you ask?
Oprah resides in a 20,424 square foot mansion that sits on a 40-acre estate in Montecito, CA. Known as the Promised Land, the mansion is secluded in the hills and despite its vast size, it is practically impossible to get very close to.
The Promised Land has 6-bedrooms, 14-bathrooms, a gourmet kitchen (obviously), 10 fireplaces (for the cold California months….?), two home theatres (one inside and one outside of course), a large guesthouse with a private pool, a wine cellar, and tennis courts. The property is also home to lots of gardens as well as avocado and fruit orchards.
And why is it named The Promised Land? During a recorded tour of her main house, Oprah filled us in on the name by saying “The Promised Land, because Dr. King said he would not get to the promised land but one day we might. And so that’s why I called it that… because I think it’s a fulfillment of the promise that Dr. King spoke of.” Wise words from the media mogul herself.
How much is Oprah Winfrey house worth? Oprah paid a whopping $50 million for the place in 2001. Oprah’s house is now worth over $100 million thanks to the insane renovations, landscaping, and of course the celebrity factor.
What does Oprah Winfrey house look like? Her main house in Montecito is nothing short of a mansion. It has a Neo-Georgian architecture design. It has a long narrow drive with red brick on either side leading up to the main entrance and is completely surrounded by beautiful trees and other lush green landscape. It overlooks stunning views of both the ocean and mountains.
When she bid farewell to her 25-year streak on The Oprah Winfrey Show, Oprah got to The Promised Land to settle in and realized she had created a museum feel instead of a home.
To fix it, she redesigned the entire home to be more livable and held a “yard sale” where the public could come bid on items to support her girls school in Africa.
How big is Oprah Winfrey’s house? Oprah Winfrey’s house sits on over 40-acres of land. The house is over 20,000 square feet!
Fun Fact! Oprah’s Emmy Award Winning show Super Soul Sunday on the Oprah Winfrey Network was filmed under the massive oak trees located on this very property.
Check out more Oprah House Photos here!
Oprah Properties in Montecito (Current)
In early 2016, Oprah dropped $28.85 million on a neighboring property known as Seamair Farm Estate. The expansion boasts four bedrooms, five bathrooms, an outdoor pool, tennis court, home cinema, and a lake. The Farm Estate home even has all the equipment and stables fit for an equestrian center.
All that didn’t matter to Oprah, though. As far as we can tell, Oprah’s goal was to expand her fortress. We here at Velvet Ropes took a trip up to the property and scored these exclusive photos… She’s demolished everything!
As of 2023, the lot remains vacant and no further details on her plans for the property are known.
In October 2019, Oprah expanded again when she bought actor Jeff Bridges’ estate, which, you guessed it, neighbors her 2016 addition. She paid Bridges $6.85 million for the four-acre property.
Here’s a map to help break it all down:
Oprah Houses Montecito (Former)
Oprah offloaded two of her Montecito properties in 2021 and 2023. Her first sale was a neighboring property of her mega mansion. The ranch-style home was purchased by Winfrey in 2007 for $7 million and boasts 3,376 square feet of living space as well as 4 bedrooms and 5.6 acres of land.
According to Dirt, the home was purchased by Hollywood film producer and director, Rawson Marshall Thurber for $14.23 million in March, 2023.
In 2022, Oprah sold another of her Montecito estates to actress, Jennifer Aniston, for $14.75 million! Winfrey had only owned the property since Jan, 2021 but apparently decided the Tuscan-style farmhouse wasn’t a keeper.
Oprah had initially paid only $10.48 million for the home, meaning that she made a decent profit off the house sale – pocket change for someone as uber wealthy as this lady!
The home was built in the late 1990s and boasts 4 beds as well as 4,320 square feet of interior luxury living space.
Where Does Oprah Live in Santa Barbara?
Many people mistake Montecito for Santa Barbara. Oprah’s house is not in Santa Barbara, but it is very close! Montecito is, shall we say, the uber-rich section of the Santa Barbara area.
Oprah Winfrey House Orcas Island, WA (Former)
In May, 2018, Velvet Ropes broke the story that Oprah had purchased a sprawling waterfront estate on Washington State’s Orcas Island for $8.28 million. Named The Madroneagle Estate, this super secluded compound has 4-bedrooms, 3-full bathrooms, 2-half bathrooms, and boasts 7,303 square feet of luxurious living space.
In addition to the main house, there is also a 4-bedroom, 3-bathroom guest house on the property. The home features lots of artisan touches as well as natural lighting and gorgeous views of the ocean. We have an entire blog post about this home, and all the details that we uncovered, here: Oprah House Orcas Island.
Surprisingly, after only 3 years of ownership, Oprah parted ways with this gorgeous property for $14 million in 2021. She still owns several commercial businesses in the area though!
And head over here for literally hundreds of photos of Oprah House Orcas Island!
Oprah Winfrey House Telluride, CO (Current)
Oprah spent all her years filming The Oprah Winfrey Show residing in Chicago. Having sold her Chicago Water Tower Place Complex in 2015 for $4.625 million, she then went on to purchase a $14 million ski chalet just a few months later.
Covering almost 9,000 square feet, the chalet is located in the mountain village of Telluride, Colorado and provides Oprah with a snowy getaway as a break from her always-on-the-go lifestyle. Ahhhhh, the life. The super high-tech home boasts 5-bedrooms, 6.5 bathrooms, and a chef’s kitchen.
Noteworthy features include a game room equipped with a pool table and wet bar, an indoor hot tub that can fit up to 7 people at once, and guest house. Lots of large windows look out onto the gorgeous gardens and trees surrounding the property. There’s even a glass bridge off of the living room that leads to Oprah’s master suite!
As well as her Colorado home, Oprah also owns 2 mansions in Montecito, California, another in Maui, Hawaii, one in Alpine, New Jersey, an estate in Florida, and several others in areas including Chicago and Nashville. Who knew one person needed so many homes?!
Check out more Oprah House, Telluride Photos here!
Oprah Winfrey House Maui, Hawaii (Current)
Where does Oprah live on Maui? Oprah’s house Maui, which she reaches by her private jet, of course, covers an incredible 163 acres. Her beautiful Maui mansion is set in the idyllic Hana area.
Oprah’s Hawaii home is a 21st-century Farmhouse and has more of a personal touch than her other homes, says her decorator. When Oprah first purchased the Hawaii house it had a small porch, a kitchen that needed a large amount of work, and low ceilings that made the home feel cramped.
The new and improved abode features multiple french doors that open onto the porch and balcony, providing numerous opportunities to step outside and enjoy a gorgeous view of the ocean and surrounding property.
After what was meant to be a small project turned into a full-blown renovation, the Maui home incorporates loads of personal and real touches that truly represent Oprah’s personality. With large mansions dotted around the rest of the U.S, the ranch in Maui gives Oprah a smaller, more relaxed and cozy place to reside. But don’t be fooled – it’s still a mansion by all accounts.
In addition to her property in Maui, Oprah also picked up an addition 870 acres of land in Maui in the Kula region in 2023, not far from her already massive property there. The mogul paid $6.6 million for the additional acreage and now owns a whopping 1,000 acres of land in Maui!
What Are Oprah’s Hobbies?
So, what does Oprah Winfrey like to do? Well aside from her career as a media genius and TV personality, Oprah also enjoys spending time doing philanthropy work, she loves to read, and she really loves spending time with her dogs. Oprah is also an avid gardener. Her celebrity friends are now accustomed to receiving random baskets of fresh produce right from her garden.
What Car Does Oprah Drive?
Oprah is the proud owner of a Volkswagen Beetle worth just over $25,000. But let’s get real…she has many others! Aside from her fleet of Cadillac Escalades fit with drivers who are at her every whim, Oprah recently bought a new Tesla.
Oh, and Tyler Perry gave her a pimped out Bentley a few years ago.
In addition to her ground transport, what would Oprah be without a private jet?! Her Global Express XRS has a spacious all-leather interior and can fit between 8 to 14 passengers. How do we get signed up?!
How Much Does Oprah Make?
In 2016 Oprah’s media empire raked in an unbelievable annual income of $315 million. Woah. As of 2023, it’s estimated the entertainment mogul now makes an annual income of $190 million.
How Much Is Oprah Worth?
Ok, prepare yourself for this one. No like really, you may need to take a seat if you’re not already. As of 2023, Oprah Winfrey’s net worth was a humongous $2.5 BILLION. O.M.G. Yeah, that’s Billion. With a B.
Between her lucrative days on her talk show, her brand ambassadorship for Weight Watchers, her acting roles, and her very own network, The Oprah Winfrey Network (OWN), which has skyrocketed in popularity, Oprah’s net worth is on the rise. Let’s just say, Oprah ain’t strugglin’.