Real estate is a high-stakes game. In Montecito, famous home flippers like Ellen DeGeneres and Adam Levine have made second fortunes by purchasing and selling some of the area’s most opulent properties. Oprah Winfrey is the most recent A-lister to cash out, with papers showing that she sold a substantial residence in two separate deals totaling around $17 million. The agreements were initially reported by Siteline Santa Barbara.

Winfrey discreetly paid $10.5 million for the property in early 2021. Fred Shuman, who ran a hedge fund in New York, and his wife, Stephanie, were the sellers. They had spent years putting together the 2.1-acre compound, which had a Mediterranean-style main house, two small cottages, and lush gardens.

Because the home was never officially listed for sale, the facts of what transpired over the next 18 months are hazy. However, Winfrey appears to have divided the former Shuman estate into two halves and sold each half to separate buyers, both of whom were friends of hers. The two modest cottages were sold for $2.3 million to Bob Greene, Winfrey’s longtime personal trainer and property manager, in mid-August. The next week, actress Jennifer Aniston paid about $14.8 million for the main house, which is in the Mediterranean style.

While there are no images of the new Aniston home floating around, decades-old permit paperwork and other tax data reveal some home specifics. The Shumans spent $2.8 million for the so-called “Tuscan farmhouse,” which was built in 1998. The couple renovated the property in 2008, and it now features four bedrooms, three full baths, and one powder room in more than 4,000 square feet. On the highly forested grounds of more than an acre, there’s also some type of modestly isolated guesthouse or solitary gym facility.

Aniston will also like the green lawns, well-kept gardens, entertainment terraces, magnificent oak trees, and a motor court that can comfortably accommodate fifteen automobiles. The lengthy driveway is gated, and the home is hidden from view from the road. A listing from decades ago cites the home’s “panoramic beach and mountain vistas,” which were probably a strong selling feature here.

Winfrey still owns several other properties, including the far larger estate just next door to Aniston’s new house—a $30+ million property she surreptitiously bought back in 2012 from Diandra Luker, actor Michael Douglas’ ex-wife. The main house on the OWN network, though, is still her 66-acre “Promised Land” estate (below), which is somewhere in Montecito and has a 20,000-square-foot palace in the middle.

Aniston’s primary abode will most likely remain the opulent Los Angeles mansion she purchased in 2012 for $21 million. The “Friends” star has completely refurbished the midcentury modern home created in 1965 by famed architect A. Quincy Jones, which is located on a hilltop in beautiful Bel Air. The house was shot by Architectural Digest in 2018.