A Peek Inside Oprah Winfrey's Real Estate Portfolio
Now that we’ve all (hopefully) caught up on Oprah's Favorite Things, it's time to look at another curated list from the multi-hyphenate media mogul: her real estate portfolio. Since becoming America's top-rated talkshow host in the late 1980s, Oprah Winfrey has accumulated $150 million worth of proprieties, from a mountain retreat in Telluride to a chic Maui hideaway. Below, a look inside Oprah's impressive homes.
Primary Residence, Montecito, CA
It's hard to imagine that Oprah spends a lot of time at home, but when she does, she spends her time at her primary residence in Montecito, California. This staggering home sits amongst a long list of other A-listers' abodes, including Gwyneth Paltrow, Jennifer Aniston, and Ellen DeGeneres, to name a few. The 42-acre estate includes a tennis court, movie theatre, sprawling pool area, terraced gardens, and a 6000-square-foot guest house.
Seamair Farm, Montecito, CA
One property on the sunny West Coast clearly wasn't enough. In 2015, Winfrey began the expansion of her Montecito estate, known as "The Promised Land." She purchased Seamair Farm, an equestrian ranch nested just beside her main property for a whopping $28.8 million, CNN reported. In addition to its horse tracks, stables, and grazing fields, the 29-acre farm also holds fruit orchards, a swimming pool, and fish ponds, making it a true outdoor oasis.
Spanish Revival–Style Home, Montecito, CA
In her latest addition to her Montecito estate, Winfrey purchased a home in 2019 from actor Jeff Bridges and wife Susan Geston for nearly $7 million, according to the L.A. Times. The Spanish Revival–style compound holds everything you could ask for, including a pool and pool house, expansive gardens, gym and chef's kitchen. This four-acre complex brings her combined Montecito property to a whopping 70 acres.
Ski House, Telluride, CO
Oprah first purchased property in the affluent, buzzy ski town Telluride, Colorado in 1994, when she bought a cabin with a view of the San Juan mountains. Then, in 2014, she purchased nearly 60 acres of land in the town of Mountain Village that borders the Telluride Ski Ranches area for $10.85 million. A year later in 2015, she purchased a high-tech $14 million Telluride home from tech entrepreneur Bob Wall, Curbed reported. Tucked in the lush mountainside, this five bed and six-and-a-half bath is equipped with many luxe features, but our honorable mentions include the built-in ski-in, ski-out trail, state-of-the-art movie theatre, and 56-foot-long underground wine cellar.
Farmhouse in Maui, HI
Oprah Winfrey holds the keys to quite an impressive piece of land in the paradise of the pacific. In 2003, she purchased two properties in Maui, totaling 163 acres, and setting her back about $5.3 million dollars, the Daily Mail reported. With the help of architectural designer Jeff Wooley and friend and decorator Ellie Cullman, she spent years renovating and perfecting every inch of the property. This included changing the structure of the house, moving staircases, and raising ceilings. Our favorite addition? The wrap-around porch perfect for taking in those beautiful Hawaiian sunsets.
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