Not only is Oprah Winfrey a media mogul, but she is also a real estate mogul, who is making moves in the Montecito, California market. In 2021, the 68-year-old TV personality bought a 2.1-acre estate with a stunning “Tuscan farmhouse” and two small cottages on the property for $10.5 million. She then split up the homes and sold them to two very famous faces. Jennifer Aniston landed the Mediterranean-style main home for almost $14.8 million, and Winfrey’s trainer Bob Greene snatched up the cottages for $2.3 million. That means the OWN network founder enjoyed a $6.6 million profit.
Aniston will enjoy an acre of land at her new estate with the 4,000-square-foot residence boasting four bedrooms, three full bathrooms, and one half-bath, according to Dirt. The Morning Show star also has a detached guesthouse for company or to turn into an onsite fitness studio. The ultra-private area means that she can relax knowing the prying eyes of the paparazzi are far away. The home isn’t even visible from the street and of course, the estate is gated.
The real reason to move to Montecito is for the “panoramic ocean and mountain views,” giving Aniston the best of both worlds. Her new home has plenty of room to run around and offers lush landscaping with plenty of shade from the mature trees planted on the grounds. If she wants to have a few Friends over, Monica, Chandler, and Ross can park in her motor court which holds up to 15 cars.
If Aniston gets lonely, she can walk next door to visit Winfrey’s $30 million compound, which shockingly isn’t her main residence. She lives full-time on a 66-acre mega-estate with a 20,000-square-foot mansion in a nearby Montecito neighborhood which is aptly named, “Promised Land.” Ah, the lives of the uber-rich really do hit differently.
Before you go, click here to see which celebrities own the most homes around the world.