The high-stakes game of real estate Monopoly continues in Montecito, where celebrity home flippers like Ellen DeGeneres and Adam Levine have earned second fortunes via buying and selling some of the area’s most extravagant estates. The latest A-lister to cash out is media titan Oprah Winfrey, who records and has lucratively sold a large estate in two separate transactions totaling roughly $17 million. Siteline Santa Barbara first reported the deals.
As part of the $10.5 million deal, Winfrey quietly bought the property in early 2021. The sellers were New York hedge fund manager Fred Shuman and his wife Stephanie, who built the sprawling complex over many years; it featured a Mediterranean-style main house, two small cottages and lush grounds.
The details of what transpired over the next 18 months are somewhat vague since the property was never publicly offered for sale. The former Shuman estate was divided into two parts, and Winfrey appears to have sold each half to different buyers, both of whom were friends. Bob Greene, Winfrey’s longtime personal trainer and property manager, bought the two small cottages for “.3 million in mid-August. Jennifer Aniston bought the Mediterranean main house for nearly .8 million the following week.
While there are no photos floating around of the new Aniston villa, decades-old permit documents and other tax data provide some home details. The Shumans acquired the so-called “Tuscan farmhouse” in 1998 for $2.8 million. The couple renovated the property in 2008; today, it includes four bedrooms, three full baths and one powder room in more than 4,000 square feet. In addition to the heavily wooded premises, which span over an acre, there is some sort of detached guesthouse or standalone gym.
Among the amenities Aniston offers are grassy lawns, gardens that are well-maintained, terraces for entertaining, mature oak trees, and a motorcourt that can accommodate fifteen cars. A decades-old listing mentions the home’s “panoramic ocean and mountain views,” likely one of the home’s biggest selling points. The long driveway is gated, and the house is invisible from the street.
Winfrey still owns a number of other homes, including the much larger estate right next door to Aniston’s new house – a $30 million compound she quietly acquired in 2012 from Diandra Luker, an ex-wife of actor Michael Douglas. Even so, the OWN network founder’s main residence remains her 66-acre “Promised Land” estate in Montecito, which features a 20,000-square-foot mansion anchored by a 66-acre plot of land.
