2005
Following her split from Pitt, 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. Not much is publicly known about the house, which is likely how Aniston preferred it.
2006
Aniston 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.
2011
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, but no less charming. It featured hardwood floors, vaulted ceilings, 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.
That same year, the former Friends star shelled out $7.01 million for two 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. 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.
