Real estate is risky business. Ellen DeGeneres and Adam Levine have made fortunes by reselling the most luxurious properties in Montecito. Oprah Winfrey, a media magnate, recently sold a large estate in two transactions for $17 mιllιon. Siteline Santa Barbara initially reported the transactions.


Winfrey secretly paid $10.5 mιllιon for the home at the beginning of 2021. The 2.1-acre, multi-parcel complex, with a main mansion designed in the Mediterranean style, two tiny cottages, and lovely grounds, was constructed over several years by New York hedge fund manager Fred Shuman and his wife Stephanie.

The 18 months after the property was never publicly listed remain unclear. Winfrey appears to have divided the former Shuman estate and sold each half to her pals. Bob Greene, Winfrey’s longtime trainer and property manager, bought the two modest villas for $2.3 mιllιon in mid-August. Jennifer Aniston bought the Mediterranean main house for $14.8 mιllιon the following week.

The new Aniston villa has no images, but decades-old permit paperwork and tax data reveal its specifics. The Shumans bought the “Tuscan farmhouse” for $2.8 mιllιon in 1999. In 2008, the couple renovated the U-shaped house, which now has four bedrooms, three full baths, and one powder room in almost 4,000 square feet. The thickly wooded, over-acre property has a small isolated guesthouse or gym.

Aniston will also have green lawns, well-kept gardens, terraces for parties, large oak trees, and a motorcourt that can fit fifteen cars. The long gated driveway hides the house from the street. The home’s “panoramic ocean and mountain views” presumably sold it decades ago.

In 2012, Winfrey purchased the $30+ mιllιon ranch next door to Jennifer Aniston’s new property from Michael Douglas’ ex-wife, Diandra Luker. The OWN network’s founder resides on her 66-acre, 20,000-square-foot “Promised Land” property in Montecito.

Aniston will presumably keep her $21 mιllιon Los Angeles home. The “Friends” star renovated the midcentury modern Bel Air mansion designed by A. Quincy Jones in 1965. In 2018, Architectural Digest photographed the residence.