Inside Her Massive Real Estate Portfolio

Inside Her Massive Real Estate Portfolio

Oprah Winfrey has built an enviable empire. With an estimated net worth of $3.5 billion (yes, billion!), the beloved businesswoman has created a network of endeavors tied to philanthropy, media production and distribution (she recently produced the movie The Color Purple), and so much more. Considering how well-traveled Winfrey is, with personal and business connections all over the country, it’s no surprise the former talk show host has put down roots in multiple locations. For the past two decades, Montecito, California, has remained her main hub. But the multi-hyphenate has also owned homes in nearly every region of the United States, with properties in Illinois, Florida, Hawaii, Colorado, and Washington state. We’ve gathered the highlights of her vast real estate portfolio below.

1985: Winfrey Buys a Chicago Condo

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A year before Winfrey’s iconic talk show, The Oprah Winfrey Show, first aired nationally in 1986, the media mogul made one of her first big real estate moves by purchasing a condo in Chicago’s Water Tower Place for an undisclosed amount. Located along the Magnificent Mile, the city’s bustling commercial district, the condo was the first of many she’d own in the building. According to the Chicago Tribune, she bought three other units surrounding the original one: a roughly $1.06 million unit in 1992; a $1.5 million unit in 1993; and a $1 million unit in 1994. She combined the four units into one massive duplex that totaled 9,625 square feet and consisted of four bedrooms, five full bathrooms, and two half bathrooms. In January 2014, Winfrey listed the duplex for $7.75 million. It sold for nearly $4.63 million in 2015.

1995: Winfrey Secures a Home on an Exclusive Florida Island

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Winfrey stepped up her real estate game in 1995 when she purchased a penthouse condo on the exclusive Fisher Island for an undisclosed amount. Located off the coast of Miami, the 216-acre, man-made island is home to many celebrities. Winfrey’s abode boasted four bedrooms and six bathrooms across 6,170 square feet. Not to mention, it featured 20-foot ceilings and an oceanfront terrace. Plus, the building came with every coveted amenity you can imagine. Winfrey sold the unit for $6.5 million in 2001 to the former chairman of Campbell’s Soup, according to Mansion Global.

2001: Winfrey Sets Her Sights on California and Snaps Up a Chicago Property

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In 2001, Winfrey officially invested in the city that would become her longtime home: Montecito, California. She purchased a sprawling estate in the celebrity-dense location for around $50 million. At the time, the sale was one of the highest for a private home in the state and the country, according to the Los Angeles Times. The original 42-acre property—known as the Promised Land— included a 23,000-square-foot Georgian-style house, a 6,000-square-foot guesthouse, a pool, and a tennis court. The estate still acts as Winfrey’s main residence today. She has since bought and sold surrounding properties, resulting in around 66 acres with additional structures on site.

Winfrey also bought a surprisingly modest four-bedroom, Colonial-style home in Chicago’s Elmwood Park suburb for just $298,000. She renovated the 1941 property, updating the not-so-glamorous features like the roof, gutters, and garage door along with the home’s heating and cooling system. She reportedly never lived there. The more than 2,000-square-foot home sold for $375,000 in 2018. With that sale, she had no remaining real estate in Chicago.

2002-2003: Winfrey Makes Major Property Investments in Hawaii

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Winfrey began acquiring land in Maui, Hawaii, in 2002. According to the Chicago Tribune, she purchased three properties totaling more than 117 acres for $17 million that year. The following year, she snapped up another three properties for approximately 49 acres with a price tag of more than $8 million combined. At the time, some of her properties had buildings on them while others didn’t. One such building is a ranch that Winfrey transformed into an inviting, island farmhouse with the help of decorator Ellie Cullman. While the project started as a small renovation, it quickly turned into a major project. Architect Jeff Wooley helped alter the floor plan, raise the primary bedroom ceiling, install French doors, and add a wraparound porch. The interiors were refreshed with a bright, breezy color palette and countryside-inspired fabrics and motifs. “I love, love, love my house,” Winfrey said of the Maui getaway in 2006. “It’s a gem, so sweet and exquisite. Such a real, normal house. It feels like a nice blanket. A lovely and soft cashmere one.”

Today, Winfrey owns roughly 1,000 acres on the island. Her most recent purchase was in 2023 when she bought a whopping 870 acres for nearly $6.6 million in Kula, which is located in the Upcountry region of Maui.

2014: Winfrey Purchases Land to Build a Colorado Mansion

Winfrey set out to build a mountain hideaway when she purchased nearly 60 acres of land in the town of Mountain Village that borders the Telluride Ski Ranches area for $10.85 million. Unfortunately, she ran into a legal issue when a retired nuclear physicist sued her for trail access rights. “I don’t care if Oprah is a neighbor, but if she is going to cut off access to trails, I don’t find that acceptable,” the physicist told The Denver Post. While the lawsuit was eventually dropped, there haven’t been any reports on whether she followed through with building a home on the land.

2015: Winfrey Buys a Colorado Home and Expands Her California Estate

The media mogul expanded her Colorado real estate portfolio the following year by purchasing an impressive $14 million Telluride home. The high-tech home boasts five bedrooms, six and a half bathrooms, and tons of impressive features—including a 56-foot-long wine cave, private cable railroad to the ski slopes, and a heated driveway (to name a few!). She reportedly bought the 8,700-square-foot residence to use as a base while overseeing the construction of a new home on the land she acquired in 2014.

In 2015, Winfrey also embarked on the first expansion of her Promised Land estate in California by purchasing a horse farm called Seamair Farm for nearly $29 million. The 23-acre estate consists of a main house designed by architect Cliff May that’s complete with a big backyard, pool, and patio. The property is designed to house horses, so it has a large circular paddock, multiple stables, and training areas. Not to mention, the sprawling estate boasts two private wells, a fish pond, fruit orchards, and green lawns.

2018: Winfrey Bets on a Waterfront Estate in the Pacific Northwest

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Windermere Orcas Island

Winfrey values a good vacation home (and we can’t blame her!). She expanded her collection of dreamy getaways in 2018 when she dropped nearly $8.3 million on a 43-acre estate on Orcas Island, which is part of Washington state’s San Juan Islands. Known as Madroneagle, the waterfront property comprised a main four-bedroom, five-bathroom house spanning 7,303 square feet at the time. The rustic sanctuary featured reclaimed woodwork, floors with radiant heat, a stone fireplace, and a kitchen with a built-in pizza oven. Other enviable amenities included a sauna, Asian garden, and wine cellar. There’s also a nearly 3,000-square-foot guesthouse on site. Winfrey eventually sold the estate for $14 million in 2021, citing that she was too busy to spend time there.

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Windermere Orcas Island

2019: Winfrey Makes Another Big Home Acquisition in California

Practically the queen of Montecito, Winfrey increased her California real estate holdings by purchasing a four-acre property for $6.85 million from actor Jeff Bridges in late 2019. The Spanish Revival-style compound put her total acquisitions in the area at 70 continuous acres valued at $86 million at the time. The three-bedroom, two-and-a-half-bathroom home was remodeled by Bridges and his wife Susan Geston after mudslides in 2017. The interiors maintained the 1919 home’s original character while featuring modern amenities. The property also included gardens, orchards, a pool house, a guest house, and horse facilities.

2021: Winfrey Quietly Invests in Another California Residence

A couple of years later, Winfrey quietly bought a Tuscan-style farmhouse in Montecito for $10.5 million. The estate’s main home consisted of four bedrooms and three and a half bathrooms. It also included two cottages and gardens across just over two acres. Winfrey didn’t hang onto the property for long. In 2022, she sold the main home to Jennifer Aniston for $14.8 million. According to the New York Post, Winfrey sold the other part with two cottages on it to her personal trainer and property manager, Bob Greene, for $2.3 million.

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