Oprah Winfrey Just Sold Part of Her Vast Montecito Estate for $17.2 Million

For many years, Oprah Winfrey’s home base has been her Promised Land estate, a roughly 66-acre compound in the coveted Hedgerow District of Montecito. Now word has it the media titan has quietly sold off a piece of her multi-structure property, specifically a historic Spanish Revival ranch on four acres she picked up from Oscar-winning actor Jeff Bridges in 2019 for $6.85 million, the same price he originally paid five years earlier. Siteline Santa Barbara first reported the off-market transfer, which was inked for about $17.2 million.

Next door to her Seamair Farm outpost designed by architect Cliff May, the Bridges ranch was first listed for sale in late 2013 for $8.5 million. Winfrey waited almost six months to buy the place, after the price tag had been slashed to $7.5 million, and then ultimately wound up paying even less.

Restored and renovated through the years, the bucolic spread dates to 1919 and was originally designed by esteemed local architect James Osborne Craig. The main stucco and terracotta-roof house has two bedrooms and four baths in roughly 3,500 square feet across a single level with rich hardwood floors, soaring exposed-beam ceilings, leaded windows, and five curved fireplaces.

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Highlights, per the most recent listing, include formal living and dining rooms, plus a spacious family room that connects to an eat-in kitchen outfitted with quartz countertops, a green ceramic-tiled backsplash, and high-end appliances. A spacious fireside primary suite comes with a bay-windowed sitting area, dual walk-in closets, and a sleek bath sporting heated teak floors, a pedestal soaking tub, and a marble and glass shower.

French doors throughout open to the bucolic grounds, which host grassy lawns surrounding gardens, an expansive red brick courtyard centered on a boulder-encased fire pit, and a pool with a spillover spa, along with multiple guesthouses, a barn, and horse stables.

Winfrey, who became the first Black woman to appear on Forbes’ billionaire list in 2003, maintains a roughly $150 million real estate portfolio stretching from California to Hawaii and beyond. In 2021, she sold another Montecito property to Jennifer Aniston for $14 million, but she still owns dozens of homes, including several in the Montecito area alone. The Mississippi native also has a chalet-style ski retreat in the Telluride town of Colorado and controls some 1,000 acres of land on the Hawaii island of Maui.

The buyer’s identity remains under wraps, but rumors are swirling that Ellen DeGeneres and Portia de Rossi might be looking to dip their deep-pocketed toes back in the U.S. real estate waters after selling off most of their holdings and decamping to England last year. Who knows? Stranger things have happened.