Oprah Sells $14 million Montecito estate to Jennifer Aniston

Oprah Winfrey is cashing out of Montecito, selling her large ocean and mountain view estate in two separate transactions for about US$17 million.

According to The Dirt, the talk show host was able to offload both properties to close friends, with Friends star Jennifer Aniston purchasing the main house for nearly US$14.8 million.

While Winfrey’s longtime personal trainer and property manager, Bob Greene picked up the two small cottages for US$2.3 million in mid-August.

Winfrey initially purchased the 2.1-acre estate in early 2021 for US$10.5 million from New York hedge fund manager Fred Shuman and his wife Stephanie.

Built in 1998, the “Tuscan farmhouse” was sold the following year to the Shumans, who paid US$2.8 million. 

The U-shaped structure includes four bedrooms, three full bathrooms and one powder room in more than 371sq m of living space.

There’s also a small, detached guesthouse or standalone gym building on the heavily wooded property, which span more than an acre.

Aniston will also be able to enjoy grassy lawns, well-kept gardens, terraces for entertaining, numerous mature oak trees and a motor court that can easily accommodate 15 cars. 

The long driveway is gated, and the house is invisible from the street. 

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Rowan Crosby

Rowan Crosby is a senior journalist at Elite Agent specialising in finance and real estate.