Oprah Winfrey bought a four-acre Montecito Estate from Jeff Bridges for $6.85 million; six years later, she sold it for $17.2 million

In 2019, Oprah Winfrey bought a four-acre Spanish Revival property in Montecito from actor Jeff Bridges for $6.85 million, folding it into her sprawling "Promised Land" estate near Santa Barbara, California. Six years later, in late 2025, she quietly sold that same four-acre parcel for $17.2 million to Maroon 5 frontman Adam Levine and his wife, the supermodel Behati Prinsloo, as reported by Robb Report, more than doubling her original investment while still holding on to the rest of her roughly 66-acre Montecito compound today.Oprah Winfrey's purchase of the Montecito Estate from Jeff BridgesJeff Bridges and his wife, Susan Geston, had owned the century-old ranch since 2014, restoring it after mudslide damage before listing it for sale. They initially sought close to $8 million.Winfrey, whose primary "Promised Land" estate sits next door in Montecito's Hedgerow District, ultimately secured the home for $6.85 million in 2019, slightly less than Bridges's asking price. The purchase extended her existing compound, which she began assembling in 2001 and, per Robb Report, later expanded in 2015 with the neighbouring Seamair Farm, to roughly 70 acres in total.Inside Winfrey's four-acre Spanish property in MontecitoThe single-level main house, built in 1919 by architect James Osborn Craig, spans about 3,500 square feet with two bedrooms and four bathrooms. Formal living and dining rooms are anchored by five fireplaces, with beamed ceilings, hardwood floors, and oversized windows throughout. The primary suite includes dual walk-in closets and an ensuite bathroom with heated teak floors, a soaking tub, and a glass-enclosed shower. French doors open onto a brick patio with a fire pit. The grounds also feature a pool and spa, a guesthouse, a poolhouse, a carriage house, and equestrian stables.Oprah Winfrey sold the Montecito Estate for $17.2 millionWinfrey sold the four-acre parcel off-market in late 2025 for $17.2 million, according to Architectural Digest, which credited local outlet Sightline Santa Barbara as having first reported the deal. The buyers were identified as Maroon 5 singer Adam Levine and his wife, model Behati Prinsloo, according to Robb Report, who purchased the property without it ever being publicly listed for sale.The sale came roughly three years after Winfrey sold a separate Montecito property, the former Shuman estate, to actress Jennifer Aniston for $14.8 million in 2022. Even after parting with the Bridges parcel, Winfrey retains more than 60 acres of her original "Promised Land" estate in the Hedgerow District of Montecito.What the $17.2 million sale means for Oprah's real estate portfolioThe sale netted Winfrey a profit of roughly $10.35 million after six years of ownership, more than doubling the $6.85 million she originally paid Bridges back in 2019. It marks the latest in a series of adjustments to her real estate holdings, which are estimated at around $150 million, spanning her Montecito compound, roughly 1,000 acres in Hawaii, and a ski chalet in Telluride, Colorado.Get the latest Bollywood & Entertainment News, and more. Download the TOI app.Give your child the gift of confidence! Claim your exclusive TOI Masterclass spot today!