Oprah's home looks way different than you think

It may come as no surprise to you that Oprah Winfrey has owned (and still owns) 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, the talk show queen's home and surrounding property look quite a bit different than you're probably imagining. We did some digging and found pictures to give give you a sneak peek into her not-so-humble abode. Winfrey has shown to be quite the private person when it comes to her personal space, so where we couldn't find pictures, we dug up detailed descriptions so you can imagine yourself right there with Ms. Winfrey herself.


It's in a small town

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

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

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

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.

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Things you didn't know about the Obamas' marriage

Has there ever been a cuter couple than Michelle and Barack Obama? The charming couple enamored the world before ever setting foot in the White House, and continues to do so years after the end of Barack's presidency. Together with their daughters, Sasha and Malia, the former first family is still beloved, and their life seems like the stuff of fairy tales.


Things have not always been easy for the Obamas, though. Michelle and Barack have an epic love story that spans decades, but, like any other couple, have faced their fair share of hardships. In many ways, their challenges were even greater because they have been in the public eye for so long. Yet, through it all, they manage to stay happy and in love. What's their secret? To figure that out, we need to take a closer look at their relationship. Here's everything you didn't know about the Obamas' marriage.

Sparks flew from their very first meeting

While they were drawn to each other from the first time they met, Michelle was reluctant to date Barack. She was 25 and he was 27, but as a first year associate at Chicago's Sidley & Austin, a corporate law firm, Michelle was Barack's mentor when the first-year law student worked at the firm in the summer of 1989. "He sounded too good to be true," Michelle told David Mendell, author of Obama: From Promise to Power (via The Washington Post). She initially dismissed him as a "good-looking, smooth-talking guy." The fact that he was her subordinate, and her belief that "the only two black people" at the firm dating would be "tacky," delayed the beginning of their relationship.

Barack told Oprah that he was "struck by how tall and beautiful [Michelle] was," saying that working with her was "the luckiest break of my life." After Michelle turned down multiple requests for a date saying it would be inappropriate, she finally agreed to go out with him after he offered to quit his job for her. Michelle took Barack up on the date, but didn't make him leave his job.

Barack's desire to help the African American community won Michelle over

Even after she began dating Barack, Michelle wasn't sure right away that it would work out. Growing up in a family that lived paycheck to paycheck, Michelle worried that a life with Barack might be unstable. She told the Hyde Park Herald (via The Washington Post) that the future president "was really broke." He had a "cruddy" wardrobe and a rusted out car. "I thought, 'This brother is not interested in ever making a dime,'" she said.


Still, Michelle was drawn to Barack. On a date at a Chicago church, where Barack was meeting with people he had worked with as a community organizer, Michelle saw his passion for helping poor African-Americans. "He talked about the world as it is, and the world as it should be," she said in a speech at the 2008 National Democratic Convention. "And he said that, all too often, we accept the distance between the two, and we settle for the world as it is, even when it doesn't reflect our values and aspirations." Michelle was won over by Barack's idealism, and the rest is history.

Barack didn't want to get married at first, believing it to be a "meaningless institution"

Impossible as it is to imagine, the Obamas' celebrated marriage might not have happened if Michelle had been a little less persistent. At the end of the summer of 1989, Michelle continued to work in Chicago while Barack returned to Harvard to finish law school. According to The Washington Post, Barack was dedicated to the relationship and madly in love with Michelle, but he didn't believe that marriage was necessary, calling it a "meaningless institution."

Michelle kept turning up the pressure, though, wanting a decades-long marriage like her parents who, at the time, had been going strong for 30 years. In 1991, Barack finally surprised Michelle with a ring after she began to talk once again of marriage, telling her "That kind of shuts you up, doesn't it?" It might not have been the most conventional of proposals, but it was an effective one. The two were married the following year, taking their commitment to the next level.

Struggles with infertility put a strain on their marriage

Life wasn't all smooth sailing for Michelle and Barack once they were wed. In a 2018 interview with Good Morning America, Michelle said that she had suffered a miscarriage 20 years earlier. The loss was a heavy emotional blow. "I felt like I failed because I didn't know how common miscarriages were because we don't talk about them," she said. "We sit in our own pain, thinking that somehow we're broken."


Michelle underwent fertility treatments to conceive Malia and Sasha, and the process was another ordeal. Michelle had to inject herself daily for several weeks. Barack, who was serving in the state senate at this point, was "swallow[ed up] by work," Michelle wrote in her memoir, Becoming. This, she said, "left me largely on my own to manipulate my reproductive system into peak efficiency." While the process was grueling, Michelle said that Barack remained "sweet" and "attentive" throughout the entire journey.

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