The success of Jennifer Aniston's illustrious acting career is reflected in her body of work; but it's also evident in the homes she's bought and sold over the past few decades. Born in Los Angeles, Jennifer Aniston was raised mostly in New York City. But since the Friends star skyrocketed to fame on the 1994 hit TV series, she's resided in various California properties. Those include a Beverly Hills mansion she once shared with her now ex Brad Pitt, a midcentury modern home she always knew she'd own, and a Montecito farmhouse that she bought from Oprah Winfrey in 2022. Despite this stable of California real estate, Aniston did attempt to relocate back to the East Coast circa 2011 (more on that below!). She definitely has the real estate bug; in a 2018 interview, she said that if she wasn't an actress, she'd be an interior designer, explaining, "I love the process. There's something about picking out fabrics and finishes that feeds my soul." We're right there with you, Jen.
Ahead, dive into everything we know about The Morning Show star's real estate moves—including the design styles she's gravitated toward over the years. We've even noted a few places she's rented for further insight into her preferred style.
The One Where It All Began
When Aniston started filming Friends, which premiered in 1994, she was living in a home perched atop Los Angeles's Laurel Canyon. While we don't have her exact move-in and out dates, we do know that the home recently hit the market for $2.6 million. The property boasts a primary residence, an A-frame guest house, a pool house, and an office-slash-studio. See inside each of the spaces here.
2001: Aniston and Brad Pitt Buy a Beverly Hills Home
Step back into the early aughts for a moment. It's the summer of 2000. Aniston and Brad Pitt recently wed in Malibu, where their $1 million nuptial events involved a caviar wall and a star-studded guest list. The following year, the pair kicked off their married life by securing a $13.1 million home in California's Beverly Hills. Spread across 12,000 square feet, the French Normandy-style home was originally built in 1934. The former couple spent three years renovating it, adding heated marble flooring in the kitchen, a screening room, and a pub-style bar area, according to Architectural Digest. Plus, they built a multimillion-dollar tennis court and a guest house on the property. You can see photos of the home—from its checkerboard kitchen flooring to its alfresco dining area—here.
After their divorce in 2005, Aniston and Pitt sold the home for $28 million in 2006. Most recently, it hit the market for a cool $56 million in 2019. It sold for $32.5 million in 2020.
2005: Aniston Rents a Malibu Beach House
Following her split with Pitt, Aniston reportedly rented a Malibu bungalow. When she first moved in, the home was "dark and depressing" but a "quickie makeover" helped turn it into a cozy hideaway that was more representative of her taste at the time compared to the home she shared with Pitt, Aniston told Vanity Fair. "Brad and I used to joke that every piece of furniture was either a museum piece or just uncomfortable," Aniston told the outlet of their shared abode. "He definitely had his sense of style, and I definitely have my sense of style, and sometimes they clashed. I wasn't so much into modern."
2006: Aniston Secures Her Beverly Hills Dream Home
"I never doubted the house would be mine one day," Aniston told AD of the first home she bought after parting ways with Pitt. The home in question? A property built by renowned midcentury modern architect Harold "Hal" Levitt circa 1970. Initially, Aniston fell in love with the 10,000-square-foot home's 14-foot-tall front doors. After she purchased it for $13.5 million in 2006, she teamed up with designer Stephen Shadley to give the home an extensive renovation, which took nearly two and a half years. The result: a Balinese-inspired, indoor-outdoor retreat. Think koi ponds (one of which the living room opened up to!), Brazilian cumaru (hardwood) eaves, and a lanai with heated travertine floors. She nicknamed the property "Ohana," which Lilo & Stitch fans know means extended family in Hawaiian. Aniston listed the home for $42 million in 2011. A couple of months later, the home sold for between $37 million and $38 million.
2011: Aniston Rents With Justin Theroux, Briefly Invests in New York City, Then Moves to Bel Air
While Aniston was dating actor Justin Theroux in 2011, the pair rented out a two-bedroom, two-bathroom home in California's Beverly Hills. Valued at $3 million, the 1,761-square-foot home came furnished. While modest compared to the other homes Aniston lived in, the residence had charming features including vaulted ceilings, hardwood floors, and multiple fireplaces. You can browse photos here.
The same year, Aniston bought two condos in New York City's West Village for just over $7 million. She intended to combine the two units—a one-bedroom penthouse with a wrap-around terrace on the 18th floor and a one-bedroom unit on the 17th floor—to create a more than 2,000-square-foot duplex in the pre-war building. While she was eager to return to the city, she cited troubles with paparazzi as a factor in her decision to ultimately sell the condos. She sold them at a loss for $6.5 million in 2012.
If you thought that was a lot of real estate moves in a short time span, think again. In 2011, Aniston also swiftly picked up a nearly $21 million Bel Air estate. She told AD that the 1965 property was "the furthest thing from what [she] wanted" when it came to the design. Aniston and Theroux spent two years renovating the 8,500-square-foot property with the help of designer Stephen Shadley, along with other creatives, to take the midcentury house from minimal to inviting. Highlights of the remodel include hand-painted wallpaper, silk rugs, and Abstract Expressionist paintings. Outside, they reimagined the small gardens, terraces, and the pool. Aniston and Theroux, who married in 2015, lived in the home together. They announced their split in 2018, and Aniston still still owns the residence today.
2022: Aniston Buys a Montecito Farmhouse From Oprah Winfrey
After seemingly taking a break from buying and selling real estate, Aniston purchased a California farmhouse from Oprah Winfrey for $14.8 million. The four-bedroom, three-and-a-half-bathroom home is located in Montecito, where many stars have settled in recent years including Prince Harry and Meghan Markle, their children, and chickens. The residence sits on just over one acre and was only one part of Winfrey’s estate. According to the New York Post, Winfrey sold the other part with two cottages on it to her personal trainer and property manager, Bob Greene, for $2.3 million.
