While winning an Emmy and a Golden Globe Award for her performance on the hit TV series Friends might be among Jennifer Aniston’s proudest moments, the fruits (and fortunes) of her illustrious acting career can be measured in many ways. There’s the estimated $90 million she made over that show’s 10-year run; there are the 70-plus acting credits she currently has to her name; and, perhaps the most tangible, there is the impressive real estate portfolio she has amassed over the years.
In the past two decades, the A-lister has bought and sold (and rented) a handful of properties—from the Beverly Hills mansion she shared with her ex, Brad Pitt, to the pair of condos she invested in amid a stint in New York circa 2011, to the Montecito, California, farmhouse she bought from Oprah Winfrey in 2022 and currently lives in. Each residence of the serial renovator is proof that her interest in design extends far beyond fashion and generation-defining hair. Ahead, we take a closer look at every home Aniston has owned—plus a few she has rented. Clearly, she’s moved beyond coffee-shop waitress life—and we’re here for it.
1990S: LOS ANGELES HOUSE, CALIFORNIA
Early in her Friends years, Aniston was renting a home overlooking Los Angeles’s Laurel Canyon. Built in 1936, the four-structure compound—known as the Crown Jewel—features two bedrooms, two baths, a pool house, and an A-frame guesthouse complete with its own kitchenette. The hilltop home has played host to myriad prominent Tinseltown figures over the years, including the Academy Award–winning cinematographer Néstor Almendros, actor-producer Beach Dickerson, and Hollywood hustler Scotty Bowers. Who’s to say this house’s wisdom didn’t give Aniston added inspiration in her iconic portrayal of the funny, spoiled Rachel Green?
While Aniston’s exact move-in and -out dates remain unknown, she resided there during much of the production of Friends, which premiered in 1994. While the star-studded property has since changed hands several times, it was recently listed last fall for an eye-watering $2.6 million, according to Robb Report.
2001: BEVERLY HILLS HOUSE, CALIFORNIA
While Aniston’s real estate beginnings weren’t all that humble, she certainly leveled up after she tied the knot with Brad Pitt. In 2001, a year after their nuptials, the couple put down $12.5 million for a 12,000-square-foot Beverly Hills mansion. The Normandy-style estate was built in 1934 and originally designed by renowned Southern California architect Edwin Wallace Neff. Aniston and Pitt spent three years renovating it, adding heated marble flooring in the kitchen, a screening room, a pub-style bar area (with wood floors from a 200-year-old French château), and a multimillion-dollar tennis court and guesthouse.
A year after their divorce in 2005, the couple sold the home for $28 million. In 2019, it landed back on the the market for $56 million; in 2020, it sold for $32.5 million.
2006: MALIBU BEACH HOUSE, CALIFORNIA
Following her split with Pitt, Aniston reportedly rented this Malibu bungalow circa 2006, which was more up her alley, style-wise. “Brad and I used to joke that every piece of furniture was either a museum piece or just uncomfortable,” Aniston told Vanity Fair of their former 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.”
When Aniston moved in, she told the outlet that the beach house was “dark and depressing” but a “quickie makeover” helped transform it into a space she felt right at home in. The oceanfront home stands as a quaint (for such an A-lister) testament to her love of the California coast.
2006: BEVERLY HILLS HOUSE, CALIFORNIA
Everybody needs a divorce present, no? Introducing the first home Aniston bought after splitting up with Pitt, a property built by renowned midcentury modern architect Harold “Hal” Levitt circa 1970 that was going for $13.5 million. From the moment Aniston saw the house, she knew it was hers, though it took seven months for the former owner to agree to sell it.
Aniston tapped designer Stephen Shadley to give the 10,000-square-foot home an extensive two-and-a-half-year renovation. The end result was a Balinese-inspired aesthetic, complete with koi ponds (in, yes, the living room), a lanai with heated travertine floors, and Brazilian cumaru (hardwood) eaves. She called the house Ohana, a reference to the Hawaiian ideal of extended family. In 2011, Aniston listed the home for $42 million and sold it a couple of months later for about $35 million, Curbed reported.
2011: WEST VILLAGE CONDOS, NEW YORK CITY
Is it the end of Aniston’s West Coast era? In 2011, while dating the actor Justin Theroux, she doled out $7.01 million for two condos in a prewar building on the opposite side of the country, in Manhattan’s West Village. The aim was to combine the two units—a one-bedroom apartment on the 17th floor and a one-bedroom penthouse with a wraparound terrace on the 18th floor—to create a 2,000-square-foot duplex. But alas, she sold both units at a loss in 2012 for $6.5 million, citing privacy issues due to the paparazzi. The apartment changed hands several times, including Andy Cohen who bought the penthouse in 2022, according to Brown Harris Stevens listing agent Frans Preidel.
2011: BEL AIR HOUSE, CALIFORNIA
Of course, Aniston wasn’t about to sit idly by after her East Coast relocation fell through. Within the year, she snagged a nearly $21 million Bel Air estate designed by Quincy Jones. She once again brought on Stephen Shadley, along with other creatives, to give the midcentury house an inviting refresh. The remodel included hand-painted wallpaper, silk rugs, and Abstract Expressionist paintings. In the courtyard, small gardens and terraces overlooked a chic pool. Aniston and Theroux lived in the home together, marrying in 2015 before announcing their split in 2018. But Aniston kept the house.
2022: MONTECITO HOUSE, CALIFORNIA
After a decade-long stretch of no real estate purchases, The Morning Show star bought a $14.8 million Montecito home from media titan Oprah Winfrey, joining A-list neighbors—like Ellen DeGeneres, Ariana Grande, Katy Perry, and Orlando Bloom, to name a few—in this fast-evolving celebrity hotspot about two hours northwest of Los Angeles. The four-bedroom, three-and-a-half bathroom Tuscan-style farmhouse was built in 1998 and has been heavily renovated over the years.