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.

When you think "billionaire," you normally don't think of "farm" — and neither did Oprah Winfrey when she purchased her Hawaiian home. "I knew it had been farmland in the past, but I didn't seriously imagine continuing that tradition," she explained on her website. However, after considering Hawaii has about 90 percent of its food imported, Oprah decided it was in her best interest to grow fresh food for her and her community right from her vacation home.

It was after speaking with fitness expert Bob Greene, who had helped her lose weight, that she realized growing her own foods was the way to grow — er, we mean, go. Greene explained that a majority of our food lacks essential nutrients because of the pesticides used. Growing her own food was a way to control that, so Oprah began to build her farm in the biggest way possible — on the side of a dormant volcano 4,000 feet above sea level. Her property grows over 100 different kinds of fruits, veggies, and herbs. "We're already producing 145 pounds of food each week," Oprah revealed in 2013.

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.'"

A property manager and friend of Oprah Winfrey's was scared someone would buy a piece of Hawaiian property with a stunning ocean view and fill it up with condos. This encouraged Oprah to buy all 163 acres and built herself a cozy house. "It feels like a nice blanket," Oprah once said of the estate. "A lovely and soft cashmere one." Sounds expensive.

Oprah deemed this one of her many vacation homes and hired designers to make it the customized, quaint home of her dreams. "She already has a large home in Santa Barbara — this seems to go back to something real and personal," Oprah's decorator, Ellie Cullman, told O, The Oprah Magazine. "It's a great house for her and two or three friends." That's exactly what Oprah prepared for when she purchased the property, it seems.

Upon spotting an electric scooter she liked, she bought five of them. "I needed it in every color so when people come to visit me in Hawaii, we will have the bikes," she told "CBS This Morning." Um we're still waiting for our invitation!

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.

In 2013, Oprah Winfrey decided it was time to downsize. "I knew my house was impressive," she revealed on Oprah.com. "I mean, just about every guest I ever invited for dinner told me so as they perched on the edge of the opulent sofa trying not to get fingerprints on anything." It was then that she realized that she needed to make her home feel more cozy and less cultured.

However, downsizing means something completely different to a billionaire like Oprah. All the things Oprah decided to get rid of were enough to fill three large tents. She auctioned off items that ranged from furniture to dolls to electric scooters. "It is my idea of a yard sale," she told "CBS This Morning."

Her yard sale ended up pulling in over $600,000, according to "CBS This Morning," but Oprah didn't keep any of it. Naturally, she didn't need the funds, but she knew others who did. All of the money went directly to The Oprah Winfrey Leadership Academy for Girls that she built in South Africa.

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."

Like any other billionaire in the world, Oprah Winfrey has a private chef, but unfortunately, "he doesn't work every day," Oprah wrote on Facebook, so when it's time for her to have a meal, she sometimes finds herself craving a specific restaurant. However, that restaurant may just be on the other side of the country. Yet and still, what Oprah wants, Oprah gets. One of her "Favorite Things" happens to be crab cakes. One day for lunch, she divulged to Harper's Bazaar, Oprah and her partner Stedman Graham "had fabulous crab cakes flown in from Pappas in Baltimore."

Lunch happens to be Oprah's favorite meal of the day, and she likes to share with others. "If Stedman isn't here," she explained to the publication, "I will invite others over — all the people I'm interested in talking to or meeting. I had Jennifer Lawrence up for lunch, Chrissy Metz, Princess Ameerah of Saudi Arabia." No big deal.

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.

It's no secret that Oprah Winfrey has expensive taste — and her artwork is definitely no exception. In 2015, the star auctioned off "500 lots of English, French, and continental furniture, decorative arts, paintings, prints, drawings" and more, according to Artnet. Then in 2016, Oprah sold a single painting to a collector for a whopping $150 million. Per Bloomberg, it was one of the largest private art transactions of 2016. The painting, titled "Portrait of Adele Bloch-Bauer," was created in 1912 by artist Gustav Klimt. Oprah purchased it back in 2006 for "only" $87.9 million. Two years beforehand, she reportedly even let the Museum of Modern Art display it for visitors. By the time she sold it, the painting's value had increased by a whopping 71 percent.

The first painting in Klimt's collection, which Oprah did not own, was sold for $135 million in 2006, which at that point was the most amount of money ever exchanged in art history. Oprah made $15 million more off of hers since it's such a classic portrait — or maybe it didn't hurt that Oprah was the one selling it.

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.

Ever since 1996, Oprah Winfrey has been recommending her favorite books for the world to read as a part of her official book club. It only makes sense, then, that this book lover and billionaire would have a large library located in her main California home. Its shelves hold over 1,500 books, which can be enjoyed while curled up on a nearby floral armchair.

Oprah's book collection includes special leather-bound copies of her official book club picks as well as rare first editions of classic novels curated by her personal book dealer Kinsey Marable. "We decided to do a run of first-edition Pulitzers when we first met," he divulged to O, The Oprah Magazine. Needless to say, those books are worth a pretty penny. Oprah even has a 12-volume collection of novels with golden portraits of their authors adorned on the spines. Everything the woman touches seems to turn to gold.

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.

Considering Oprah Winfrey is universally admired and, well, fabulous, anyone would want Oprah to be the godmother to their child — or boat. In 2019, Oprah was officially appointed the godmother of Holland America's Nieuw Statendam. Yes, a cruise ship.

The tradition of becoming a ship's godparent actually dates back to ancient times as a way of bringing safety to the ship and is considered an honor, according to The Telegraph. Oprah is only the second person to be named a godparent of one of Holland America's cruise ships. The first was Desmond Tutu, former Archbishop of Cape Town, South Africa.

Nieuw Statendam is 975 feet long and can hold over 2,500 guests, all of whom can enjoy meditation in the mornings, a special reading room, and some of Oprah's other "Favorite Things" as they sail around the world. The trip is "all inspired by O, The Oprah Magazine's dedication to living your best life," the cruise line revealed. It truly sounds like Oprah is living hers.

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?

Oprah Winfrey's favorite hobby has always been hopping into her bathtub. "I major in bathtubs," she told Vogue in 2017. "I spend my time looking for the best possible bathtub a woman can buy." So it only makes sense that her home once held the most amazing one anyone has ever imagined. "It was carved to the shape of my body," she told The Late Late Show with James Corden. Creating her most prized possession began by having a model made of her body, which was used to create the perfect tub made of onyx marble for her. "Bathing is my hobby," she said. "I take it seriously." We can certainly see that!

Unfortunately, when it came to later remodeling her bathroom, her custom-made tub was something Winfrey parted with. It didn't fit the new room anymore, and it was an emotional moment for her. Though she could easily buy herself a new bathtub, she noted on her website that the tub "represented wealth" that she'd "truly made it." She explained, "It made me feel special. Lots of people have nice houses, but not many have a hand-carved-out-of-one-piece-of-onyx tub." Knowing Oprah and how important bath time is to her, she's likely replaced her tub with something special.

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!"