Oprah flips Montecito estate to Jennifer Aniston for $15M

Deal for “Tuscan farmhouse” part of two adjacent parcels sold for total $17M

From left: Oprah Winfrey and Jennifer Aniston with her Montecito estate
From left: Oprah Winfrey and Jennifer Aniston (Google Maps, Getty)

Oprah Winfrey has peeled off a piece of her Montecito real estate portfolio with the $14.8 million sale of a house to Jennifer Aniston.

The billionaire media mogul sold two properties in the beachside town near Santa Barbara for $17.1 million, including a 4,320-square-foot home to the star of “Friends,” Dirt.com reported.

Winfrey bought the “Tuscan farmhouse” early last year for $10.5 million. The sellers were New York hedge fund manager Fred Shuman and his wife Stephanie, who had assembled the 2.1-acre spread.

Their complex included the Mediterranean-style villa, two small cottages and grounds.

Winfrey appears to have split the former Shuman estate and sold each half to different buyers, both of them friends, according to Dirt.

In mid-August, she sold the two small cottages to Bob Greene, her longtime personal trainer and property manager, for $2.3 million. The next week, she sold the Mediterranean-style manse to Aniston for $14.8 million.

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Built in 1998 and renovated by the Shumans a decade later, the U-shaped villa has four bedrooms, three baths and a powder room. It includes what appears to be a detached guest house or standalone gym, surrounded by an acre of mature oak trees behind a long private driveway.

The two-story home has grassy lawns, well-kept gardens and a motorcourt that can accommodate 15 cars. A decades-old listing mentions the home’s “panoramic ocean and mountain views.”

Forbes has pegged Winfrey’s wealth at $2.5 billion. She owns numerous homes, including a $30+ million compound she bought in 2012 from Diandra Luker, the ex-wife of actor Michael Douglas, next door to Aniston’s new home.

But the main residence for the founder of the OWN network is the 66-acre “Promised Land” property in Montecito, anchored by a 23,000-square-foot neo-Georgian mansion.

Aniston’s main residence may be her mid-century modern home in Bel-Air, built in 1965 by architect A. Quincy Jones which she bought in 2012 for $21 million. It was featured in 2018 by Architectural Digest.

Dana Bartholomew

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