All The Homes That Oprah Owns

Oprah Winfrey may be quite the billionaire media mogul, but she wasn't always that way. According to Forbes, the entrepreneur and favorite television personality is worth a whopping $2.5 billion these days. However, her climb to the top was anything but easy — it was completely riddled with hardship. Oprah was born to a single teen mom, and she was sexually abused by family members, said Parade. However, Oprah quickly left home and focused on building herself a life and career. She began working in media at a mere 17 years old and slowly worked her way up, until she finally became the host of the iconic "Oprah Winfrey Show" in 1986.

Once Oprah's show began running — which continued to do so for 25 seasons — she set her sights on many other businesses that contributed to the wealth she enjoys today. She launched her own cable network, OWN, and still owns 25% of its stock. She's a brand ambassador for Weight Watchers, and owns 10% of that company, too. Plus, she's produced films like "The Color Purple" and "Selma." So, needless to say, we can't be surprised that this underdog is the queen of the screen these days. Which also translates into cash. Throughout the years, Oprah has reinvested lots of her earnings into real estate, which has led her to own homes across the country. Here are the residences she has called her own.

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Oprah is quite the real estate mogul and has tons of properties throughout the United States. However, her number one trumps all of the rest. What she has named Promised Land — a 70-acre estate in Montecito, California — is worth a stunning $100 million. However, according to LoveProperty, Oprah got quite the steal on her 23,000 square foot home. She paid $52 million for it — and it wasn't even on the market. Actually, she attended an event here more than two decades ago and loved it so much that she immediately gave the owners an offer they couldn't refuse.

The property is truly a palace fit for a TV queen. It has lush acreage filled with romantic touches like roses and fountains, six bedrooms, two separate private theaters, a gourmet kitchen, a massive walk-in closet, and a library. It's all outfitted in an opulent Georgian style with lots of neutral, sunny tones. Outside, the place gets even better. Throughout those 70 acres, Oprah enjoys fruit orchards, a tennis court, ponds filled with fish, a pool, and a home for visitors which, at 4,000 square feet, is bigger than most peoples' regular homes. You don't have to do much to see Oprah's paradise, either. She frequently posts photos of herself in the Promised Land cooking, relaxing, and hanging out with friends. We can definitely see why — there aren't too many reasons one would need to leave this stunner.

Not all celebrities are clamoring for a Caribbean island. Instead, Oprah splurged on an island home with much greener scenery. She bought a mansion on Orcas Island, which is off the coast of Washington and is filled with tons of parks, water views, and evergreens. According to Dirt, in 2018, Oprah picked up what's known as the Madroneagle Estate for nearly $8.5 million, taking its 43 acres and 3,000 square feet of water frontage along with it. The estate dates back 15 years and includes four bedrooms throughout its colossal 7,300 square feet, but this rustic escape has many more features than just bedrooms.

Just like Oprah's main house in Montecito, the Madroneagle Estate also has a huge library for enjoying her book collection. The airy kitchen, brightened by windows on the ceiling, includes a pizza oven (since we're guessing there's no Domino's around the corner here.) Downstairs, there's a whole lineup of fun home features, such as an area for storing and tasting wine and a home office where Oprah can get some work done while away from the studio. And with the other features onsite, she sure doesn't need to rush home to California. The property also includes a woodworking studio, private fitness center, yoga studio, sauna, pond, beach access, an Asian garden ... and the list seriously goes on. Even the home for visitors has its own name — the Gallery House, a four-bedroom respite.

Orcas Island isn't the only rustic paradise Oprah likes to head to. The Wall Street Journal reported that the media mogul also picked up an 8,700 square foot home in Telluride, Colorado, for a cool $14 million in 2015. And like her other homes, this place has more than its fair share of celebrity-worthy amenities (via Curbed). The room for storing wine was designed to look like a mining tunnel, in a nod to Telluride's mining past. ("To hell you ride" — get it?) Part of that design includes water mist and mining sounds — as if its tunnel-like appearance isn't enough. Plus, a private funicular from the home that can bring up to four people to a nearby ski run is also modeled to appear as a mining car. To take in the surrounding mountain views, the abode also has six patios, one of which is in a tree and has its own firepit. 

But don't worry, the actual living space of this home is pretty amazing, too. There's a private fitness center, an entertainment room with its own bar and pool table (for after your guests tire of skiing, of course), a gourmet kitchen, a home spa, and an entirely see-through glass bridge for primary suite occupants to get to the rest of the house. Oprah sure does know how to sniff out those wild home features.

For the 25 years that Oprah hosted the "Oprah Winfrey Show," she called the Windy City home. And she had lots of real estate there to prove it. One such residence that she enjoyed during her time in Chicago was a condo that cost nearly $8 million and had the square footage to back it up. The place was more like a mansion than a condo, thanks to its nearly 10,000 square feet. Per Forbes, Oprah listed the four-bedroom space, which was once four separate units, for sale in 2014. However, there's more to this price tag than meets the eye. Just the homeowner's association fee is $9,000 per month.

Just a year before Oprah's show first hit the air, she bought what would become the basis of her fabulous, customized duplex. She spent another $3.5 million on three other units throughout the years to create the enormous space. But the condo itself wasn't the only part of this property to hit the market. A few months later, in a sort of celebrity-esque estate sale, Oprah auctioned off tons of items in the apartment, including artwork and furniture, much of it antique, according to Page Six. And Oprah, ever the philanthropist, didn't take the money and run. Instead, she donated all proceeds to The Oprah Winfrey Leadership Academy Foundation, which funds girls' education in South Africa.

This lover of real estate is not afraid of renovation, which was made clear when she purchased a fixer-upper in Hawaii and turned it into a paradise. Oprah.com said that when Oprah picked up the property — located in a secluded spot by the beach — it had a dated kitchen, a primary suite lacking light, and a floorplan that didn't flow well from the interior to the exterior as many Hawaiian homes do. To start, everything but the walls was essentially gutted. Then, a wraparound porch was installed, high-end fixtures and details were appointed, ceilings were heightened, and even parts of the home as massive as the staircase were entirely relocated.

Oprah's interior decorator and architectural designer made the place into an entirely new home — one that's reminiscent of a country estate rather than a tropical compound. Oprah's team decorated with lots of classic, 19th-century antiques to fill the space, like folk art of American farmers, a lamp shaped like a rooster, and a weather vane designed to look like a horse. Oprah said that this aesthetic makes her feel most at home — even in Hawaii — since she was raised in that type of environment. She was born in Mississippi and later lived in Kansas, Tennessee, and Wisconsin.

Chicago wasn't the only place where Oprah once had a five-star condo. Per Dirt, Oprah dropped just $660,000 on a 1,800-square-foot condo in Florida in 1996. Twelve years later, she saw quite an increase in value when she listed it for a little more than $2 million. However, this is no ordinary Sunshine State getaway. Oprah's two-bedroom Florida condo was on the ever-exclusive Fisher Island, a 216-acre haven for the rich and famous that's only accessible by sea or air. And although it's secluded, it has plenty of amenities for its A-list residents to enjoy. This includes places to play polo and tennis, eight restaurants, high-end boutiques, and a five-star resort.

Oprah's apartment had stunning ocean views and an airy, sunny ambiance. Still, it lacked a lot of the customization and upscale finishes that Oprah seems to enjoy at her other homes. So we're guessing she knew she wouldn't be spending a ton of time here. In typical Florida style, it included furnishings in neutral colors, palm-themed fans, and appliances that the typical American has in their apartment — no top-of-the-line fixtures here. It even had some odd touches — for example, one entire kitchen wall was coated in mirrors.

Oprah's $8 million condo wasn't the star's only Illinois residence. She also owned a surprisingly modest Colonial-style abode in Elmwood Park, a suburb of Chicago. According to CBS News, Oprah picked up the 2,200 square foot home a little over two decades ago for just $300,000. The house was so mysterious that its neighbors had no idea that Oprah's name was on the deed, although other residents, presumably renters, moved out before Oprah listed the home for sale in 2016.

That year, she put the four-bedroom house up for sale for $400,000. With classic elements like a brick façade, wood-burning fireplaces, and hardwood floors, we're sure a family scooped up this home in no time. However, Oprah herself never rested her head here, nor did she ever reveal why she bought the house in the first place.

Even though Oprah's Promised Land estate is astounding, it's not the only home in Montecito that she wanted to call her own. In late 2019, she also picked up a Spanish Revival-style property sold by actor Jeff Bridges, star of hits like "The Big Lebowski" and "True Grit." The Los Angeles Times reported that although Oprah got quite the deal on the place — she paid a little under $7 million for the home and four acres of land — Bridges did not. The price was exactly the same as when he bought it half a decade earlier.

It's also much more than a home — and a century-old home at that. The property that now belongs to Oprah includes lots of lush land, including gardens, several types of trees, and orchards. Plus, it's a paradise for an equestrian, since there are horse stables and a carriage house. There are two other houses here, too — a home for visitors and a pool house. Some of the home's standout features include exposed wood beams, colossal windows to see the property beyond, and high-end touches like French doors. Lots of fireplaces also warm up the space, as do heated floors and a great indoor-outdoor flow perfect for California living.

Oprah's mining-theme home in Telluride wasn't her only plan for the Colorado hotspot. Per The Wall Street Journal, she dropped another $11 million on 60 acres of vacant space in Telluride in 2014. And it wasn't even for sale at the time. Oprah simply saw the space — and its crazy views of the mountains beyond — so she made the owner an offer they couldn't refuse, reported Haute Residence. As the biggest property in the area (which is also zoned for both a house and home for visitors,) we're guessing that Oprah planned to build another dream ski home here. It was, after all, right next to the popular Galloping Goose ski trail in the Telluride Ski Resort in Mountain Village. The village is a town located 9,500 up in the air that even includes its own gondola.

But the neighbors had other plans. A man living nearby launched a lawsuit against Oprah, claiming that the home would inhibit his rights to access the trails, said The Denver Post. He ended up dropping the suit, but it doesn't seem to have mattered much. It doesn't appear that Oprah ever built a home on the land.

It seems that Oprah has her fair share of mysterious properties. (But why wouldn't you if you're worth $2.5 billion?) Per Berg Properties, she also owned a 4,800 square foot penthouse apartment in Atlanta, Georgia, that she paid more than $1.5 million for when she bought it in 2003. Then, she offloaded the five-bedroom residence in Park Place on Peachtree for $1.8 million five years later. We imagine the eight-room apartment wasn't easy to part with — this 40-floor building is the 27^th tallest in the entire city and is located in the luxe neighborhood of Buckhead, according to All Atlanta Condos.

Here, the units range up to three bedrooms, so we're guessing that Oprah combined two units to create her custom home. While the above photo isn't of her exact condo, it gives you a peek inside a unit at a similar price point. While living here at 2660 Peachtree Road, she enjoyed tons of outdoor space thanks to the unit's wraparound patios, the ability to walk to shops and restaurants, and the most modern appliances available. Surprisingly, though, it doesn't seem like other celebrities were clamoring to live here, as we don't know of any other A-listers who bought a home in the building except for one former senator. We're sure Oprah enjoyed the privacy.

Of course, Oprah had her own residence in millionaire-capital New York City. Per Daily Mail, she shelled out more than $7 million for a penthouse known for its towering windows and its 700-foot patio with unmatched views of Washington Bridge and Central Park beyond. Located on the 36^th floor of the Place 57 tower, the home also features 2,500 square feet of living space, wood floors, a dramatic arched ceiling, and the most modern kitchen on the market. It was all designed thanks to the combined efforts of three separate designers who strived to make it one of the most beautiful of its time due to its walls of glass, opulent garden, and lobby outfitted in lots of crystal details, said Place 57's website.

It had other luxe features, too, like three separate walk-in closets — perfect for this television star's presumably huge wardrobe — a hot tub, and two fireplaces to warm up the whole space on chilly New York City nights. Plus, it's right around the corner from the famous shopping of Madison Avenue. However, in 2012, Oprah decided to call it quits on the then-six-year-old apartment, which had prices that, at the time, started at an amazing $1.47 million. She listed hers for $7.9 million, which at first shocked fans — Oprah originally bought this pad in secret under the name of her BFF, Gayle King.