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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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.

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.

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.

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.

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.