Inside Oprah's Incredibly Lavish Lifestyle

Oprah Winfrey, who was named by Forbes' as one of the richest self-made women in America, has come a long way since being born poverty-stricken to a single teenage mother in Mississippi. As of June 2019, she had amassed a net worth of over $2 billion. Oprah's film roles, book club, product line, magazine, television network, and Emmy award-winning shows have raked in millions since she first appeared on our television screens as host of "The Oprah Winfrey Show" way back in 1986.

Since striking it rich, Oprah has shared the wealth. She's donated millions of it to multiple charities and has even started a few of her own, according to People. Of course, with her billionaire status, she still has quite a bit of it left over to live a lavish life. "I'm trying to live the life that I talk about, like not letting things define you," she told "CBS This Morning." "But it's hard!" We think it probably would be if we had a billion dollars too. Read on for an inside look at a few of her most extravagant indulgences.

Traveling takes up a lot of time. You have to arrive at the airport hours early, wait in line, and sometimes deal with the worst part: layovers. After years of travel — and an altercation with a fan at a terminal — Oprah Winfrey was tired of it. "I went to the phone and called my lawyer and I said, 'I'm going to do it, I'm going to get the plane,'" she explained to The Hollywood Reporter. "'This is going to be my last time waiting four hours in the Chicago O'Hare Airport.'" And so, in 1991, she waved goodbye to flying commercially and wrote a $25 million check — in full, because Oprah admitted she hates dealing with bills — for her very first private jet.

Ever since, she's been traveling in style. Oprah told Edward Enninful, editor-in-chief of British Vogue, that it was the best luxury she'd ever invested in, and we'd have to agree. "Because it means one minute you're in New York, and then the next minute you say, 'No, Edward, I think I'll fly to London! I'll do the shoot there.'"

Even for all the extravagant homes that Oprah Winfrey owns, she loves to be out enjoying nature, so, naturally, when it came to designing her California home, she needed an equally extravagant garden that she could enjoy. According to Oprah.com, she hired celebrity designer Dan Bifano to put it together and match the interior of her house. He came over and introduced Oprah to a variety of roses from which she could choose, but then came up with a truly original idea. Alongside hybridizer Tom Carruth, the designer came up with a new rose for the billionaire.

It took a total of five years to create one the largest hybrid roses ever made — and Oprah even got to name it. Instead of naming it after herself, she gave it a name to honor 18 African American women whom she admires. In 2008, the red and black Legends Rose was shared with greenhouses everywhere so whoever desires can have a garden like Oprah's. Well, maybe not exactly like Oprah's.

With the 600 rose bushes planted on Oprah Winfrey's California property, the star decided she needed a cutting room. However, as it was being built in 2003, she admitted to O, The Oprah Magazine, "I'm going to want this space for myself." As such, it became a private teahouse — and a truly perfect place to enjoy a cup of tea, soak in the sunshine, and admire the view of her flowers through a large arched doorway.

The only sounds that can be heard while inside it are the swishing of the breeze, the water trickling in her large fountain, and the birds singing outside the windows. Oprah does not allow any electronics or work to enter her tranquil teahouse. "No meetings, ever," she said. In fact, she wouldn't even allow a bathroom to be built in the space. "You don't even want to be here in this small space and hear somebody else flushing the toilet," she explained to interior designer Nate Berkus (via Us Weekly), adding, "You gotta pee, you gotta go outside."

Oprah Winfrey added a vacation home in Telluride, Colorado to her long list of real estate in 2015. The $14-million home is the perfect place to stay while hitting the slopes during ski season — or you could just stay inside and take advantage of the private spa, treetop bonfire pit, and — most importantly — the huge wine cellar. Having perfect wine is important to Oprah. "I like my wine very chilled, so when it goes into the glass you see the humidity on the outside," she dished to Harper's Bazaar. "Wine — if it's too warm — is the only thing I ever send back at a restaurant."

Naturally, Oprah's wine cellar isn't any old wine cellar. It reportedly cost nearly a quarter of a million dollars to build, The Telegraph revealed. Dubbed the "wine mine" by the publication, the 56-foot-long room was designed to resemble an underground mine with an antique cart running on old tracks to view all 1,600 bottles that it can hold. The whole ride takes about 60 seconds and the experience is complete with speakers that play the sounds of creaky wood and leaking water.

Oprah Winfrey always looks so well put together, but she admits it takes an entire team to accomplish the feat. "I normally have, for a magazine cover, 28 people working to help me look good," she once admitted on her talk show. There's someone to constantly straighten her clothes, another to fetch the perfect pair of shoes, a person to make sure not a hair is out of place, and even "somebody who if a collar falls down, that's their job to make sure that the collar stands up," Oprah continued. And it's not just during a photo shoot that Oprah has people helping her look her best.

Famous fashion designers sometimes stop by her living room for a private trunk show before releasing next season's designs to the public. "Brunello Cucinelli came up from Los Angeles, and I chose everything that I wanted from their spring line," Oprah shared with Harper's Bazaar in 2018. What a lavish life Ms. Winfrey has. And yes, we're jealous.

By 2016, Oprah Winfrey owned various homes, but that didn't mean she couldn't add one more. Oprah discovered a unique property in California that featured a beautiful five-bedroom house surrounded by over 20 acres of land, orchards, and a fish pond. Oh, and it happens to be in the same star-filled neighborhood as Ellen DeGeneres and Drew Barrymore's homes. Interestingly, it's also a horse farm, according to E! News.

The historic ranch, complete with covered stables and designated horse riding areas, was one where many champion ponies had been raised and it was the first time in almost 40 years that the farm had been listed for sale, CNN reported. However, E! News revealed that Oprah didn't actually want any of the horses that came along with the estate. "Obviously, she is a very smart buyer and does have an amazing vision for this property," the manager of the sale told CNN. We hope so, but then again: it only cost her $28.85 million.

When Oprah Winfrey uttered the inspiring words "a new day is on the horizon" during a powerful speech at the 2018 Golden Globe Awards, it had people everywhere encouraging her to run for president in 2020. While Oprah was hesitant to take it seriously, people were ready to throw money at the celeb to do it. "I had people — wealthy, billionaires — calling me up and saying, 'I can get you a billion dollars. I can run your campaign,'" she told People. "That many people saying something made me think, 'Am I at least supposed to look at the question?'"

Though her opportunity to run in 2020 has come and gone, it still has us all wondering if we'll be seeing Oprah pulling to be president in a later election year. After all, she has made it her life's mission to help those around her as much as she can, and what better role is there to do so?

However, Oprah told People she'd prayed about and asked for a sign "so clear that not even I can miss it." She continued, saying, "And I haven't gotten that," she admitted to People. Of course, that could change. #Oprah2024, anyone?

Like many of us who love to spoil ourselves, Oprah Winfrey enjoys spending a day at the spa. However, her experience happens to be a bit different than the rest of ours. She likes to hop aboard her private plane to spend the day at a special spa in the Himalayas.

The Ananda spa, located on the scenic side of a mountain in India, is the country's very first destination spa. Between yoga classes with beautiful landscapes to 80 different body and beauty treatments, it's the perfect place to spot some pretty famous people. Everyone from Winfrey to Brad Pitt has been seen there, according to Elle.

On Oprah's Lifeclass tour, she revealed she "was trained by a yogi for the first time" at the spa and was taught her that yoga isn't only about stretching and deep breathing. Rather, Winfrey's yogi helped her to let go of negative thoughts. "Ananda is a gift," she wrote in their guestbook (via Elle). "And a blessing!"