Jennifer Aniston’s houses over the years have almost all been situated on the West Coast, despite the fact that the actor became an icon with her role as one of New York’s most endearing fashionistas on Friends. (Fun fact: The show celebrated its 30th anniversary this year on September 22.) The native Angeleno likely prefers the spaciousness of Hollywood living, which no doubt allows her to really exercise her design talents.

“I love putting homes together and creating spaces,” she told The Wall Street Journal last fall. “I can walk into a house and see what it needs. And it’s a fun process. Some people dread it. It can break up relationships. I thrive during that process.” Based on her numerous properties over the years, the Morning Show star’s aesthetic appears to be stylish and zen, and she has a great eye for architecture as well. Over the years, she’s picked up residences designed by star midcentury architects like Harold “Hal” Levitt and A. Quincy Jones. Most recently, she’s sought some space and distance from the fray with the acquisition of a retreat in the celebrity-loved beach town of Montecito, California. Aniston purchased the Mediterranean-style abode in 2022 from talk show legend Oprah Winfrey, who still owns property in the area. Other famous neighbors include Prince Harry and Meghan Markle, Gwyneth Paltrow, Ellen Degeneres, and more.

“If I wasn’t an actress, I’d want to be a designer,” Aniston told AD during a 2018 tour of her A.Quincy Jones–designed abode. “I love the process. There’s something about picking out fabrics and finishes that feeds my soul.” Here, we’ve rounded up the places the actor has called home over the past two decades, each with its own distinct history, aesthetic, and story.

Beverly Hills home with Brad Pitt

In 2001, a year after Aniston tied the knot with Brad Pitt, the couple shelled out $13.1 million for a 12,000-square-foot French Normandy–style Beverly Hills home. The mansion was originally built in 1934 and was designed by renowned Southern California architect Edwin Wallace Neff. (The impressive bespoke residence has long been a part of Hollywood history; Neff built it for fellow Hollywood couple Frederic March and Florence Eldridge.) Aniston and Pitt expanded and renovated the property to include a private screening room, heated marble floors in the kitchen, and (perhaps most famously) a pub room with wood floors from a 200-year-old French château. They also added a multimillion-dollar tennis court and a guest house. Aesthetically, the interior was both modern and warm, utilizing clean lines and stacked stones for an organic, inviting feel. The pair spent a total of three years renovating the space and ultimately sold it for $28 million in 2006 following their 2005 divorce. In 2019, it landed back on the market for a whopping $56 million.

Malibu beach house rental

Following her split from Pitt in 2005, Aniston reportedly rented a 1,531-square-foot beach house in Malibu for two years. The home, which belonged to Oracle cofounder Larry Ellison, featured three bedrooms and three bathrooms, and it was situated right along the coast. In a 2006 interview with Vanity Fair, Aniston shared that she gave the rental a quick makeover to imbue it with her signature cozy aesthetic. In retrospect, she said, every piece of furniture in the mansion she and Pitt had shared “was either a museum piece or just uncomfortable. I wasn’t so much into modern.” The rental, therefore, could be a place she made entirely her own. Not much is publicly known about the house, which is likely how Aniston preferred it.

Balinese-inspired Beverly Hills retreat

When the actor toured what would become her next residence, it was love at first sight. Aniston said she knew her Harold W. Levitt–designed Beverly Hills mansion was meant to be hers the moment she saw it. “I never doubted the house would be mine one day,” she told AD in 2010. She paid $13.5 million for the hillside residence in 2006, and then spent the next few years working with designer Stephen Shadley to transform it into a Balinese-inspired retreat, complete with koi ponds, Brazilian cumaru eaves, and heated travertine floors on the lanai. Aniston nicknamed the home “Ohana,” which means extended family in Hawaiian, and enjoyed hosting and entertaining in the “glamorous, old-fashioned Hollywood” retreat. She finally parted ways with the 10,000-square-foot, single-story home in 2011 after listing it for $42 million; it eventually sold for $38 million.

Beverly Hills rental

One month after Aniston sold “Ohana,” she and then beau Justin Theroux rented a 1,761-square-foot home just north of Sunset Boulevard in Beverly Hills. The two-bedroom, two-bathroom residence was considerably more modest than Aniston’s other properties, yet no less charming. It featured hardwood floors, vaulted ceilings, multiple fireplaces, and a state-of-the-art kitchen with white marble countertops. Perhaps the most enviable feature of the $3 million home, however, was its views thanks to its hilltop perch. The couple reportedly paid $20,000 a month for the rental.

West Village condos

That same year, in 2011, the former Friends star shelled out $7.01 million for two prewar condos in New York City’s West Village, one of which was a penthouse with original hardwood floors and a 900-square-foot wraparound terrace, the other of which was a one-bedroom unit one floor down. She initially intended to combine the two homes into one mega-unit that would measure over 2,000 square feet, but ultimately paparazzi issues led her to put them back on the market a few months later. Aniston sold them at a loss for $6.5 million in 2012.

Bel Air mansion

When the East Coast relocation fell through, Aniston didn’t miss a beat, snapping up a $20.97 million A. Quincy Jones–designed Bel Air mansion later that same year. She once again partnered up with Stephen Shadley (with some help from Kathleen and Tommy Clements and Jane Hallworth) to reimagine the midcentury house to be less minimal and more comfortable and inviting. At the time, the 1965 property had just been renovated by architect Frederick Fisher, and its new look was a bit too cool and minimal for her taste. “Aesthetically, it was the furthest thing from what I wanted, but I immediately had the sense that it could work,” she told AD. “It’s hard to describe, but I felt a connection.” She and Theroux spent two years renovating the 8,500-square-foot property to make it more inviting, adding hand-painted wallpaper, silk rugs, and Abstract Expressionist paintings.

“I’m all about cozy. Sexy is important, but comfort is essential,” the Along Came Polly star told AD of her design philosophy for the house. “Every corner you turn, you have an experience. Everywhere you look, you get a vista. We worked very hard to get that flow right.” Aniston and Theroux lived in the home together after their marriage in 2015. They called it quits in 2018, but Aniston still owns the residence today.

Montecito ranch

The Morning Show star seemed to go a while without any real estate purchases, but in 2022, she paid $14.8 million for a four-bedroom, three-and-a-half bathroom Mediterranean-style farmhouse in Montecito, the beach enclave about two hours north of Los Angeles. Montecito has become a celebrity hot spot in recent years, attracting the likes of Ariana Grande, Katy Perry and Orlando Bloom, Prince Harry and Meghan Markle, Gwyneth Paltrow, and more big names—and the star power even extends into Aniston’s new residence. The seller of the home was none other than Oprah Winfrey. (The talk show icon still maintains a large ranch called Promised Land in the area, so she isn’t leaving the idyllic enclave.)