Oprah’s home looks way different than you think

It may come as no surprise to you that Oprah Winfrey has owned some pretty epic properties. From her former dual Chicago condos — one with 4,607 square feet of space and the other 9,625 — to her gorgeous Hawaiian farmhouse, few homes compare to Winfrey’s. Her most extraordinary property, however, is her Montecito, California estate.

At 23,000 square feet, the Neo-Georgian mansion is not only gargantuan but also undeniably beautiful, as one would expect. However, Winfrey’s home and surrounding property look quite a bit different than you’re probably imagining.

It’s in a small town.

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Winfrey’s house is not small by any stretch of the imagination but, it is located in the relatively small town of Montecito, California. Part of Santa Barbara, Montecito features long stretches of coastline, great restaurants, and boutique shops. Oh, and a spectacular handful of celebrities including Jeff Bridges, Julia Louis-Dreyfus, Rob Lowe, Ellen Degeneres, and, of course, Winfrey. 

Degeneres even termed the town “the greatest community.” That’s pretty exciting. Though, if you decide to visit, Santa Barbara’s tourism site advises, “don’t make a fuss if you see a famous face.” Imagine coming face-to-face with the Oprah Winfrey and not making a scene. Surely easier said than done.

It’s symbolic of freedom

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Winfrey may have the pleasure of living in a great community, but privacy is no doubt still important to the media mogul. Her huge private property is just the place to unwind and relax in silence. It is also quite symbolic to Winfrey. According to an interview with Vogue, Winfrey’s Montecito estate is set on 65 landscaped acres of land that she calls the Promised Land. Why the biblical name?

She had been looking to buy a Southern plantation when she stumbled upon the property in California. Although about as far from the southeast as you can get, the home had the plantation look and feel. “I was calling it Tara II,” Winfrey explained the property’s original name to Vogue. Tara was the name of the O’Hara Planatation in Gone With the Wind. Her mind was changed one day when walking the property with her fitness guru and friend, Bob Greene. He explained to Winfrey that Scarlett O’Hara’s plantation paled in comparison and, because of that, Winfrey should come up with a better and more-fitting name. 

He told her, “The fact that you are an African-American woman from Mississippi and you get to have this … it’s deep.” Just then, the ideal name came to him. He exclaimed, “It’s a promise! It’s the Promised Land!” And so, the Promised Land estate was born. 

“I feel that every day,” she told Vogue, “… just absolute joyful contentment.”

It’s home to the Apostles

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Keeping with the biblical theme, Winfrey also made room on her property to house the 12 apostles. If you’re scratching your head wondering how that’s possible, the 12 apostles in Winfrey’s Promised Land are actually a grove of trees — 12 giant mature oaks — that Winfrey symbolically named “the Apostles,” according to Vogue. 

Fittingly, Winfrey also named the path leading to to the trees “Hallelujah Lane.” The branches of the mega “Apostles” intertwine above and beside the path forming a “gorgeous, spooky tangle.” Winfrey even has her favorite oak — Mark, Matthew, John? — and shared a photo of it on her personal Instagram, encouraging fans to post pictures of their favorite trees as well.

Although Winfrey’s home is rich with spiritual metaphors, that’s far from its only features.

There’s a New York Times room

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The Bible is not the only sacred text in Winfrey’s household, it seems. Vogue detailed the open-air stone teahouse Winfrey had built on the property to serve as a quiet space to read The New York Times and drink tea. Now that is living the dream.

“I wanted it to be intimate and to feel like a hug,” she told Nate Berkus in a sneak peek for Us Weekly. What you won’t find is a bathroom in Winfrey’s embrace-like structure. “You don’t want to even be here in this small space and hear somebody else flushing the toilet,” she told Berkus. She clarified by saying she can turn on fountains surrounding the teahouse if one wants the sound of running water but the two concurred the sound of a toilet flushing was not exactly peaceful.

According to Oprah magazine, Winfrey first planned the building to be a cutting room for flowers, but decided as it was being built that she wanted a space for herself. After it was built, Ellie Cullman, Winfrey’s interior designer, added green wicker furnishings. She may only visit her teahouse several times a year, but just knowing it exists makes her happy. “It’s my dream, having a place like this,” she said. When people question why she needs more space, she tells them, “I need it to restore myself.” Amen.

Her DIY Garden

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In 2017, Forbes named Winfrey the wealthiest female entertainer in the United States and, according to Time, she’s also one of the richest female entrepreneurs in the country. Her home is a direct indicator of her fortune and while Oprah could afford to pay others to upkeep her property, there are certain things she likes to do herself.

According to Oprah magazine, Winfrey’s tearoom faces a stunning view of Montecito and her own English garden. In it reside many different kinds of perennials and annuals. Winfrey explained that the diversity in the garden is what she loves most of all. Also a part of her English garden is a full acre of rose bushes designed by Dan Bifano, an expert rosarian — yes, that’s a thing. Despite having a specialist on the scene, Winfrey clarified, “I had my hands down in the dirt, helping plant these [roses].”

Winfrey never had a garden growing up. “All I had was the hydrangea bush that was in front of my grandmother’s porch,” she said and noted that she decided to pay homage to her grandmother with thousands of white hydrangeas planted along Hallelujah Lane. 

Winfrey even has her own vegetable garden — one she harvests herself. “I can get excited over little things,” she explained. “Just the bounty of it, the fact that this just came out of the ground.”

The dining room makeunder

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Despite the lavishness of her outdoor space, the interior of Winfrey’s home is really quite modest — especially given its size. Her dining room is no exception. 

In 2013, Winfrey decided to redecorate her Montecito home. She explained in Oprah magazine, “This [dining room] is a very grand space, but I don’t want to live in a grand space anymore. I want dinners to reflect my heart and spirit. I want people to feel free to ask for seconds!” 

Even though Winfrey felt the dining room was stuffy back in 2013, it was still understated compared with what you might expect. It featured a table with just enough room for ten guests, a sideboard, a pale pink floral area rug, and a few gold accents and fixtures.

Winfrey’s updates, as shown in one of her instagram videos, gives the room a more modern feel. Still, she continues to keep things simple and it seems she definitely does have a space to host dinners that reflect her “heart and spirit.” Whether anyone feels comfortable enough to ask Winfrey for seconds, however, may be an entirely different story.

There’s nothing kitsch about her kitchen

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Before Winfrey decided to makeover her Montecito home in 2013, her kitchen featured a fireplace. Talk about opulence. By the time she started renovating, she realized it wasn’t very useful. “When you have friends over, everybody tends to end up in the kitchen,” she noted for Oprah magazine, “I like being there, so I’m getting rid of the fireplace and the pizza oven to gain some space. Everything else is staying put.”

As the third largest shareholder in Weight Watchers and the iconic spokeswoman of the brand, it makes sense she’d want to make better use of her kitchen space. In fact, in one of her Weight Watchers ads she’s shown cooking not in some random set kitchen, but her actual kitchen in Montecito. And, why not? Her kitchen is gorgeous, after all. Winfrey also routinely shares Instagram photos and video of herself from within her kitchen, even one featuring top chefs cooking for her “Queen Sugar” party.

Her living room is for, well, living

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Winfrey’s living room pre-2013 was bright and really quite pretty. However, it just didn’t feel like “her.” Oprah magazine explained the tale in an Instagram post showing before and after photos of the room. 

Back in 2010, designer Rose Tarlow visited Winfrey’s home and, upon seeing her living room, said, “I’ve never seen such a disconnect. The house has nothing to do with you. It’s like you created what you think a person of means should have.” Ouch, that’s some tough love. Eventually, Winfrey stopped taking offense to Tarlow’s comment and started to plan her living room renovation. 

In order to help guide Winfrey, Tarlow asked, “What physical thing would you least like to live without?” Winfrey’s answer? Books — lots and lots of books. So, that’s exactly what she added to the space. Winfrey is certainly much happier with her living room sans silk slipcovers. “My living room now feels like a womb with a view to the ocean. It’s cozy, it’s styled comfortable, it’s me,” she said. 

That nearly $29 million addition, though

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Near the close of 2015, Winfrey purchased a 23.26 acre estate adjacent to her Promised Land home for $28.85 million, Variety reported. Once known as Seamair Farm, a fully functional horse ranch, it borders just about the entire side of Winfrey’s original property. The ranch had three caretaker or staff residences on site, as well as a barn, stable, several riding rings, and a two-acre avocado orchard. Additionally, the property features two private water wells, which would no doubt be useful during California’s prolonged droughts. 

No word on what Winfrey decided to name her new property, if anything at all. Heaven? Garden of Eden? Promised Land II? We’ll have to wait and see.

Mostly mudslide-proof

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California can’t seem to catch a break, first with devastating wildfires and then mudslides. Montecito was hit especially hard by the latter. 

In a FaceTime interview with Ellen Degeneres on The Ellen Show, Winfrey elaborated on the damage, including waking up just before four in the morning to her dogs barking. When she peered out of her bedroom window, she saw a mountain that looked to be on fire. Later, she discovered there had been a gas fire that caused an explosion. All the while, Winfrey wasn’t even aware of the damaging mudslides that were rapidly occurring. It wasn’t until the next day that she realized the extent of the destruction.

Winfrey and her neighbors’ homes were in a voluntary evacuation zone, but many still experienced significant damage. “All of my neighbors homes are gutted,” she told Ellen, “The neighbors out back, their houses are gone — just gone.” Luckily, Winfrey’s home was miraculously okay. “My house is up on a knoll,” she told Degeneres, “I felt really safe because the house is on a hill. I felt the house was safe.” 

In an earlier Instagram post, Winfrey reassured her followers that her property was fine, sans some minor mud damage, and highlighted how her situation does not compare to that of her neighbors. Like a good neighbor, Winfrey was there. Despite not having gas or running water, she stayed put to support the Montecito community.

How Oprah went from wearing potato sacks to the top of the world

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It’s hard not to be inspired by Oprah Winfrey and her journey. This is a woman who has been through it all. As a child she lived with multiple family members who could not afford to buy her new clothes. At 9 years old she began being molested by uncles and cousins. Her mother kicked her out of the house at 14 years old, the same time that she learned she was pregnant.

Yet she rose to the very top of fame and fortune. Oprah’s name is now synonymous with success and giving. She has built an incredible legacy, and the path she took to get there is fascinating.

She always had hope

Oprah is the ultimate rags to riches story. When I see her houses and clothes now, it is so inspiring to think of where she came from. Orpah Gail Winfrey (no, that isn’t a typo) was born on January 29, 1954. Her aunt wanted her named for Orpah in the biblical book of Ruth, so that’s how it’s spelled on her birth certificate. But people weren’t sure how to pronounce it, so her name became Oprah. Oprah’s young mother was unwed and poor, so she sent Oprah to live with her grandmother until she was 6 years old.

Even though Oprah was surrounded by love as a young child, they didn’t have much else. Her grandmother worked as a maid and told Oprah that she would also grow up to be a maid. According to a profile by The Observer (via The Guardian), during this time she wore clothes made from potato sacks, which resulted in people cruelly calling her “Sack Girl.” But even as a young child, Oprah knew she was meant for much greater things.

She overcame her abusive childhood

Once Oprah’s young mother felt ready to take her back, Oprah moved out of her grandmother’s house and in with her mother. When Oprah returned to live with her mother, life took a dark turn. She was still living in poverty, but now she couldn’t even feel safe in her own home. Starting at age 9, Oprah was sexually abused by family members and eventually became pregnant at age 14. It was at that time that she first considered suicide.

“I hit rock-bottom,” Winfrey told The Hollywood Reporter. “I became pregnant and hid the pregnancy. I’d intended to kill myself actually. I thought there’s no way other than killing myself. I was just planning on how to do it. If I’d had the Internet, I might not be alive because now you can just Google how to do it.”

During her pregnancy, her mother actually decided to kick her out of the house. She was supposed to go to a detention center for girls, but fortunately they were full and could not accept her. It was at this time that she was sent to live with her father, who helped her turn things around.

Losing a child changed her life

So here she was pregnant at 14 and moving to a new state to live with a new parent. Fortunately, Oprah’s father provided a safe and loving home for her. Oprah hid her pregnancy before she ended up giving birth to a son who later passed away from complications of being born prematurely. Experiencing all this at age 14 would have broken most people, but Oprah’s father told her that this was going to be her “second chance” at life. She could now move forward and leave her painful past behind her.

“I was, in many ways, saved by that, and I made a decision that I was going to turn it around,” she told The Hollywood Reporter. Oprah did turn it around and left her painful past behind her.

She did beauty pageants

It’s hard to believe that the suicidal and pregnant 14 year-old was able to turn her life around, but she did. Oprah started trusting herself and her own instincts and followed her passions to the public eye. “I haven’t planned one thing — ever. I have just been led by a strong instinct, and I have made choices based on what was right for me at the time,” she told Makers.

Oprah started participating in beauty pageants and she went on to win the title of Miss Black Tennessee in 1972 when she was 17. Once Oprah got the taste of the limelight, there was no turning back.

She became a news anchor at age 19

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