Jennifer Aniston has been a Hollywood favorite for decades, and somehow, she keeps getting better with age. From her Rachel Green days on Friends to her Emmy-winning turn as Alex Levy on The Morning Show, the 56-year-old has proven she can do it all—act, produce, endorse, and invest.
Her career alone is enough to make anyone’s head spin: 10 years of Friends (yes, she’s still cashing in on reruns), more than 70 acting credits, hit films like Horrible Bosses and We’re the Millers, and streaming projects that keep her in the spotlight like the upcoming Apple TV adaptation of Jennette McCurdy’s memoir, I’m Glad My Mom Died. And she’s not just starring—she’s producing through her company, Echo Films, which she founded in 2008 with partner Kristin Hahn.
Then there’s the business side of Aniston. She’s previously been the face of brands like Aveeno and SmartWater, and even co-founded her own haircare line, LolaVie. She’s also a philanthropist, supporting everything from Stand Up to Cancer to animal rescues with her Clydeo Fund.
But let’s get to the fun part: her real estate. Over the past 20 years, Aniston has bought, sold, renovated, and curated a handful of homes that are as stylish as her red-carpet looks. There’s the Montecito farmhouse she snagged from Oprah Winfrey, Beverly Hills homes (some shared with exes Brad Pitt and Justin Theroux), plus a couple of New York City condos she’s since parted ways with. Here’s a closer look at the homes Aniston currently owns—and the lore behind them.
West Hollywood
Image Credit: Google Earth Aniston’s first foray into real estate came in 1995, when she scooped up this 2,903-square-foot home in West Hollywood for $742,500, roughly one year after Friends premiered. The two-bedroom, three-bath property in the Hollywood Hills has reportedly become her longtime office space—and, at one point, a star-studded rental. Isla Fisher recently revealed to The Times that she and then-husband Sacha Baron Cohen once leased the home in the mid-2000s.
Los Angeles
Image Credit: RB/Bauer-Griffin/GC Images The actress’s main residence is a midcentury masterpiece by architect A. Quincy Jones, tucked behind high gates on a 3.27-acre estate in Bel-Air. The actress bought the home in 2012 for just under $21 million and later renovated it with designer Stephen Shadley, preserving its modernist pedigree while adding personality with silk rugs and hand-painted wallpaper.
The 8,500-square-foot property—complete with gardens, a pool, and a separate guesthouse—became the setting for her surprise 2015 wedding to Theroux, cleverly disguised as a birthday party for him and attended by about 70 close friends. The couple split in 2018, but Aniston retained the house, which remains her primary residence.
In early 2025, she expanded her footprint, purchasing the neighboring five-bedroom property for $7.25 million. The newly acquired home is currently undergoing extensive renovations. Building plans suggest she’s transforming it into a guesthouse or annex to create a larger, more private compound—a move that comes after a security breach in May, when an intruder rammed through the gates of her main residence.
Montecito
Image Credit: Google Earth Aniston joined Montecito’s star-studded enclave in 2022 with the purchase of a $14.8 million Mediterranean-style mansion from none other than Oprah Winfrey. The Tuscan-inspired farmhouse, built in 1998, spans 4,320 square feet with four bedrooms, three-and-a-half baths, multiple terraces, and a gated driveway flanked by oak trees. Nestled on just over an acre, the home offers landscaped gardens, panoramic ocean and mountain views, and a large motorcourt.
Winfrey retained the two adjacent cottages, selling them separately to her longtime property manager, making the compound’s total sale around $17 million. Aniston’s acquisition places her among Montecito’s growing roster of high-profile residents, including Ariana Grande, Kendall Jenner, and Cameron Diaz. Winfrey, meanwhile, still lives at her larger “Promised Land” compound nearby.
Source: Luxury - robbreport.com
