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 show has lucratively sold a large estate in two separate transactions totaling roughly $17 million. Siteline Santa Barbara first reported the deals.
Winfrey quietly acquired the property in early 2021, paying $10.5 million. The sellers were New York hedge fund manager Fred Shuman and his wife Stephanie, who assembled the 2.1-acre, multi-parcel spread over many years; the sprawling complex included a Mediterranean-style main house, two small cottages and lush grounds.
Because the property was never publicly offered for sale, details of what happened over the following 18 months are somewhat vague. But Winfrey appears to have split the former Shuman estate into two parts and sold each half to different buyers, both of them her friends. In mid-August, the two small cottages were sold for $2.3 million to Bob Greene, Winfrey’s longtime personal trainer and property manager. The following week, the Mediterranean main house went for nearly $14.8 million to actress Jennifer Aniston.
While there aren’t any photos floating around of the new Aniston villa, decades-old permit documents and other tax data provide some home details. Built in 1998, the so-called “Tuscan farmhouse” was sold the following year to the Shumans, who paid $2.8 million. The couple gave the property a renovation in 2008; today, the somewhat U-shaped structure includes four bedrooms, three full baths and one powder room in more than 4,000 square feet. There’s also some sort of tiny detached guesthouse or standalone gym building on the heavily wooded premises, which span more than an acre.
Aniston will also enjoy grassy lawns, well-kept gardens, terraces for entertaining, numerous mature oak trees and a motorcourt that can easily accommodate fifteen cars. The long driveway is gated, and the house is invisible from the street. A decades-old listing mentions the home’s “panoramic ocean and mountain views,” which were likely a big selling point here.