Oprah has revealed her Favorite Things list for 2025—and we’re already browsing. In addition to edible luxuries like Meghan Markle’s fruit spreads from her new holiday collection, the lineup includes chic home goods such as mini Coco & Dash rechargeable lamps and MacKenzie-Childs toasters.
Now, 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, Winfrey has accumulated $150 million worth of proprieties, from a mountain retreat in Telluride to a chic Maui hideaway. Below, a look inside her 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 stays at her primary residence in Montecito, California. The 42-acre estate includes a tennis court, movie theater, sprawling pool area, terraced gardens, and a 6,000-square-foot guest house.
Seamair Farm, Montecito, CA
In 2015, Winfrey began the expansion of her Montecito estate, known as "The Promised Land." She purchased Seamair Farm, an equestrian ranch nestled just beside her main property for $28.8 million, CNN reported. In addition to its horse tracks, stables, and grazing fields, the 29-acre farm also has 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 70 acres.
Ski House, Telluride, CO
Oprah first purchased property in the ski town of 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 bought a $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, including the built-in ski-in, ski-out trail, state-of-the-art movie theater, and 56-foot-long underground wine cellar.
Farmhouse and Land in Maui, HI
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 roughly 24 acres, and costing about $5.3 million, the Daily Mail reported. (She would go on to spend a reported $40 million to increase her Hawaii portfolio to 163 acres in the next two decades.) 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.
In 2023, Winfrey added 870 acres to her Maui holdings in four separate acquisitions, per KITV. Winfrey paid $6.6 million for the agricultural parcels, which she purchased from the Ulupalakua Ranch. The sale brought her total land portfolio in the Aloha State to over 1,000 acres.
Geoffrey Montes is an associate editor at ELLE Decor with a serious love for all things real estate and design. Before that, he worked at Architectural Digest, Galerie, and Preservation magazines, covering everything from jaw-dropping listings to world-famous architects and design events like Salone del Mobile and Homo Faber.
