32 Times Celebrities Sold Homes to Each Other

The “six degrees of separation” theory seems to ring especially true in Hollywood, but celebrity homes are connection points just as often as movies, musical collaborations, or even romantic relationships. The rich and famous have the means to buy and sell opulent homes on a regular basis, meaning that some of the most lavish, coveted residences in the Los Angeles area rack up an impressive lineage of celebrity owners after a while.

Here, we’ve compiled the latest unexpected connections to emerge from the Tinseltown real estate records. Enjoy your trip down the celebrity-homes rabbit hole! 

Justin Bieber to Khloe Kardashian to YouTube star Dhar Mann

Fans of Keeping Up With the Kardashians are well-acquainted with Khloe Kardashian’s former Calabasas home, a sprawling Tuscan-style villa featuring a cavernous walk-in closet made of two former guest rooms. What fans might not realize, however, is that the 9,320-square-foot house also has quite the celebrity pedigree. It originally belonged to Eddie Murphy’s ex-wife, Nicole, who sold it to Justin Bieber for $6.5 million in April 2012. Kardashian purchased the mansion from Bieber for $7.2 million in 2014. The Good American founder then spent a substantial amount of money customizing the place (it was featured on the cover of Architectural Digest in March 2016, alongside her sister Kourtney’s sprawling estate) before selling it to YouTube star Dhar Mann for $15.5 million toward the end of 2020.

Selena Gomez to French Montana

Selena Gomez decided to kiss Calabasas goodbye in late 2015, listing her Mediterranean-style mansion for $4.495 million. A few months later, rapper French Montana snagged the five-bedroom home for $3.3 million. He made significant upgrades to the place, adding a $400,000 recording studio and painting over Gomez’s purple and turquoise walls with more neutral tones. The “Ain’t Worried About Nothin” rapper recently sold the home for $5 million.

NBA Star Paul George to French Montana

French Montana seemingly has a thing for homes with celeb pedigree. Toward the end of 2020, the rapper put down $8.4 million for a 15,873-square-foot mansion belonging to NBA star Paul George. The oversized seven-bedroom, nine-bathroom home boasts a number of stellar spaces, including a great room with floor-to-ceiling windows and a main bedroom suite with its own spa-like en suite bathroom. Perhaps one of the more unusual features, however, is the tree growing in the middle of the great room, stretching up toward the vaulted ceiling and skylight. Out back there is a basketball court, a playground for kids, and a pool.

Alexander Skarsgård to Rooney Mara to Kelly Osbourne

Rooney Mara’s gorgeous Los Feliz pad had a celebrity pedigree when she bought it, and the lineage continued when she left. In 2015, Mara bought the 2,340-square-foot midcentury-style home from Alexander Skarsgård for $2.9 million. Two years later she listed the two-bedroom, two-bathroom residence, and Kelly Osbourne ultimately bought it in June 2018 for $3.575 million.

Robbie Williams to DJ Khaled

Robbie Williams can rest easy knowing that his over-the-top Beverly Hills mansion was sold to a worthy heir—DJ Khaled. The British singer relinquished the practically regal 7-bedroom, 11-bathroom mega-mansion to the prolific producer for $9.9 million in early 2017. Amenities in Khaled’s pad include a massive home gym, an expansive kitchen with a butler’s pantry, and an outdoor kitchen, pool, and spa, perfect for throwing fantastic backyard parties. 

Charlie Sheen to Kendall Jenner

Charlie Sheen bought his sprawling Beverly Hills home for his ex-wife Brooke Mueller in 2012. But five years later a lot had changed, including his fondness for the residence. Sheen sold the property to Kendall Jenner for $8.55 million in late 2017. The model opted to revamp the home in a more minimalist style, swapping out Sheen and Mueller’s grandiose decor for a cleaner, more modern look.

Adam Levine to John Mayer

In March of 2018, Maroon 5 frontman Adam Levine sold a Beverly Hills mansion to singer-songwriter John Mayer. The former Voice coach and his wife, model Behati Prinsloo, originally purchased it in the fall of 2012 for $4.83 million and listed it for a substantial bump: $17.5 million. When they failed to attract a buyer, they lowered the asking price to $15.9 million, but it’s unclear what Mayer ultimately paid for the 7,100-square-foot, five-bedroom, seven-bathroom dwelling.

Ben Affleck and Jennifer Garner to Levine

After more than a year of trying to sell their massive Pacific Palisades family compound, exes Ben Affleck and Jennifer Garner finally found a buyer in none other than Levine. In January 2019 the singer shelled out $32 million for the property, which includes a ranch-style main residence and two other structures (one houses an office, an art studio, a gym, and a screening room; the other is a two-bedroom, three-bathroom guesthouse) and by September 2021, Levine and Behati landed their home on the cover of AD. Other big names who have lived in the home (originally built by architect Cliff May in the late 1930s) include Gregory Peck and producer Brian Grazer.

Levine to Ellen DeGeneres

And finally, Levine sold a five-bedroom Tudor-style Beverly Hills home to a star with a notorious penchant for real estate, Ellen DeGeneres, in May of 2019 for $45 million. (The talk show host has bought and sold no fewer than 20 properties in the last two decades, including one she sold to Ryan Seacrest in 2012.) Previous owners before Levine included Will & Grace cocreator Max Mutchnick and tennis champ Pete Sampras. DeGeneres sold the dwelling in April of 2021.

DeGeneres to Ariana Grande

In early 2020, DeGeneres and her wife Portia de Rossi purchased a unique Tudor-style home in Montecito, California, only to flip it back onto the market shortly afterward. Pop star Ariana Grande then saw the opportunity to expand her real estate portfolio, paying the power couple $6.75 million for the 5,500-square-foot property in June of that year. Known as the Porter House, Grande’s new home consists of two separate barns that were originally built in Surrey, England, and then had to be dismantled and reconstructed in California. Inside, lofted wood-beam ceilings and exposed brick fireplaces maintain the former barns’ rustic aesthetic. In the spring of 2021, Grande held her wedding to realtor Dalton Gomez at the home.

DeGeneres to Scooter Braun

Ellen DeGeneres and Scooter Braun both close so many real estate deals, it was only a matter of time before they’d end up swapping contracts. In March 2022, Ellen DeGeneres and Portia de Rossi paid $21 million for a lavish Montecito estate that was inspired by Alhambra Palace and just six months later they sold it off to Braun for $36 million. The 2.4-acre estate already had a bevy of amenities at the time of the couple’s purchase, so it's unclear what exactly merited that $15 million price bump. 

John Travolta to Scooter Braun

Speaking of degrees of separation, John Travolta is two jumps away from a large chunk of Hollywood after selling his 9,100-square-foot Spanish-style mansion to talent manager Scooter Braun for $18 million in January 2020. The Pulp Fiction actor and his late wife, Kelly Preston, had owned the home since 1997 before passing it on to Braun, who represents a number of popular artists, including Bieber, Grande, Demi Lovato, David Guetta, J Balvin, Hilary Duff, and many more. When Travolta and Preston purchased the place, it had six bedrooms and nine and a half bathrooms. By the time Braun scooped it up, they had upgraded the house to have 10 bedrooms, 10 bathrooms, a guardhouse, and two garages. 

Moby to Leonardo DiCaprio to Miguel

In April 2018 a stately English-traditional-style dwelling in Los Feliz passed from one socially conscious celebrity to another when musician and animal rights activist Moby sold his home to Oscar-winning actor and environmental activist Leonardo DiCaprio for $4.91 million. In the time that Moby owned the place, he substantially renovated the kitchen and other parts of the 4,644-square-foot house, but reports at the time of the sale noted that the Once Upon a Time…in Hollywood star was unlikely to enjoy the upgrades himself because he bought the place for a family member. In August of 2021, DiCaprio put the pad back on the market, subsequently selling it to singer Miguel Jontel Pimentel for $4.9 million in February of 2022. 

Jesse Tyler Ferguson to DiCaprio

Clearly DiCaprio has a sharp eye for all things design, so it is no surprise that Jesse Tyler Ferguson and Justin Mikita’s stylish Los Feliz home caught his attention. The Revenant star snapped up the 1928 Spanish Colonial–style property for $7.1 million in May 2021. This was a substantial leap from the $4.6 million the couple paid for it back in 2013. (Though, to be fair, Ferguson and Mikita had put in a significant share of time and effort into reimagining the space with the help of Will & Grace set designer Peter Gurski.) Prior to Ferguson and Mikita, several other famous names called the four-bedroom pad home, among them Gwen Stefani and Robert Pattinson.

Jeff Bridges to Oprah Winfrey

What are neighbors for? When Oprah Winfrey decided she wanted to expand her holdings in Montecito in late 2019, she looked no further than Jeff Bridges’s nearby Spanish Revival–style compound, which was up for sale. The Bad Times at the El Royale actor and his wife, Susan Geston, first listed the ranch earlier that year for $8 million, but the media mogul ultimately paid slightly less, with a final closing price of $6.85 million. The complex spans four acres, and it will likely be absorbed into Oprah’s so-called Promised Land ranch, which already measures a whopping 70 contiguous acres.

Winfrey to Aniston

As previously mentioned, Oprah’s primary Montecito property is 70-acres large, so when she bought an additional two-acre property in the town back in 2021, it wasn’t clear what exactly the media mogul would be using it for. Two years later and she’s already sold off the property in two separate deals. The property’s two small cottages went to Oprah’s personal trainer and property manager Bob Greene, while Jennifer Aniston walked away with the big kahuna: a 4,000-square-foot “Tuscan farmhouse.” The deal was off market, so little is known about the property’s interiors, but if celebrity trends are any indication, you can’t go wrong with buying in Montecito. 

DJ Steve Angello to Calvin Harris to Charli XCX

Calvin Harris ensured the musical lineage of his sleek Hollywood Hills home in the fall of 2020 when he sold it to “Boom Clap” singer Charli XCX for $5.1 million, just about three years after he purchased it from fellow DJ Steve Angello for around $7 million. The four-bedroom, six-bathroom home is perfect for entertaining, with an 18-foot-high wood-beam ceiling in the main living room, which also boasts floor-to-ceiling walls of glass overlooking the city lights below. A bar/lounge area with banquette seating similarly features an entire wall of windows overlooking a wraparound deck, and an attached guesthouse offers the perfect respite with one of the two bedrooms converted into a recording studio.

Liam Payne to Halsey

In early 2021, Halsey set about getting things ready for the July birth of their first child, Ender Ridley Aydin, with the purchase of a sprawling five-acre compound in Calabasas. The singer paid former One Direction member Liam Payne just over $10.16 million for the stunning estate, which comprises a 9,700-square-foot main house, a recording studio, a teahouse, a guesthouse, and a small working vineyard. Koi ponds and waterfalls dot the property. The main house itself boasts numerous luxuries, including a two-story library, a wine cellar, and a home theater. Payne previously claimed that the home was “haunted,” but added, “if you don’t believe in it, I don’t think it can get to you.”

Amar’e Stoudemire to Rick Ross

Rick Ross broke records with the purchase of former NBA All-Star Amar’e Stoudemire’s Miami home. The rapper paid $3.5 million—all cash—for the South Florida mansion in early 2021 and closed on the massive deal in just four days. Ross’s new place features a 7,361-square-foot main house, a 1,314-square-foot guesthouse, and a 9-car garage. The athlete had owned the home for about a decade, having paid $3.7 million for it in 2011.

The Weeknd to Madonna

The Weeknd’s Hidden Hills home found a new musical owner in April of 2021. The singer sold his 13,391-square-foot mansion, which he bought brand new in 2017, to none other than the Queen of Pop herself. Madonna reportedly paid $19.3 million for the modern farmhouse, which features seven bedrooms and nine bathrooms, as well as a wine room, a home theater, a bar area, and a five-car garage. A separate guesthouse comprises two bedrooms and two bathrooms, while an infinity pool, a full basketball court, and an outdoor living room and firepit round out the property’s many offerings. The only downside to the sale was that The Weeknd sold it at a slight loss; he paid just under $20 million for the place back in 2017.

YouTube star Safiya Nygaard to Uzo Aduba

YouTube star Safiya Nygaard’s former Studio City, Los Angeles, home is a perfect blend of East Coast charm and West Coast chill with its blue exterior and crisp white trim set against a stark contrast of palm-tree-lined steps leading up to the front door. Nygaard, perhaps best known for her YouTube video “Why I Left BuzzFeed,” sold the six-bedroom, five-and-a-half-bathroom pad to Emmy winner Uzo Aduba in May 2021 for a cool $3.1 million. Standout features include a home movie theater, a wine cellar, and a two-car garage that occupies the entirety of the lowest of three floors.

Nicole Richie to Adele

Ahead of the release of her long-anticipated new single, “Easy On Me,” Adele purchased a $10 million Beverly Hills house from none other than her next-door neighbor, Nicole Richie. The four-bedroom, four-bathroom home features a subdued, gray exterior with a custom-built chicken coop and edible garden out back. (Richie told Architectural Digest in 2017 that she purposely had the coop built in the image of her own house because she “wanted one color palette throughout.”) Adele and Richie had been neighbors since 2016 when the singer bought her first Beverly Hills mansion for $9.5 million. Richie and her husband Joel Madden originally purchased their former home for $6.7 million in 2015.

Sylvester Stallone to Adele

One of the highest price tags on this list at $58 million, the final price for the home that Adele bought from Sylvester Stallone was still $52 million less than the Rocky star was first asking. About a year on the market led to that major drop in price for the Beverly Hills 8-bedroom, 12-bathroom that sits on 3.5 acres of land. Among the estate’s many jaw-dropping amenities are a two-story guesthouse, a cigar room, and a primary suite complete with two bathtubs, a sauna, a steam room, and its own terrace.

DJ Alesso to Lena Waithe

In September 2021 Lena Waithe decided to upgrade her living situation with the purchase of a $6.4 million modern mansion that previously belonged to another arbiter of cool: Swedish DJ and record producer Alesso. The home, situated in Studio City, measures 6,587 square feet and features six bedrooms and eight bathrooms, along with all the trappings of a contemporary Hollywood palace, namely a main suite that converts into a private screening room, a pool with its own outdoor lounge area, and an infrared sauna.

Frank Zappa to Lady Gaga to Lizzy Jagger

Legendary musician Frank Zappa reportedly bought his Hollywood Hills home for just $75,000 in the ’70s, holding onto it for roughly two decades before his passing in 1993. When his family decided to list it another 20-plus years later, it went to Lady Gaga, who paid roughly $5.3 million for the pad. In a relatively limited stay compared to the Zappas’s decades of ownership, Gaga sold the home to Mick Jagger’s daughter Lizzy Jagger five years later. Few details are available about the seven-bedroom, six-bathroom home and Gaga’s potential renovations, as it was never listed for sale publicly, though we can assume she walked away with at least some profit from Jagger’s $6.5 million.

Kevin McKidd to Daveed Diggs and Emmy Raver-Lampman

Daveed Diggs and Emmy Raver-Lampman’s love for the San Fernando Valley was on full display during our tour of their colorful Sherman Oaks pad, and clearly the Broadway performers wanted to sprawl out in the area. In April of 2022 it was reported that the couple bought a Studio City home from Grey’s Anatomy actor Kevin McKidd for $5 million. McKidd himself paid $4.6 million for the all-black-and-white home a few years before.   

Taylor Lautner to Kaley Cuoco

Another San Fernando Valley spot, Taylor Lautner’s contemporary Agoura Hills home sold to Kaley Cuoco for $250,000 above asking price. Cuoco’s previous home in Hidden Hills leaned farmhouse, but Lautner’s former home is a clean-lined contemporary vision. Its lot is nearly nine acres, meaning there’s plenty of room for outdoor entertaining, including a 45-foot-long infinity edge pool and a bocce ball court, plus a covered lounge area, a barbecue station, and two firepits for a slightly chiller night in. 

Cameron Diaz to Grande

When Cameron Diaz bought this Hollywood Hills property in 2004, she already owned the home right next door, so it was assumed she was looking to expand that home. Though city documents confirm that plans were made to demolish the structure in 2009, she clearly never got around to it. No matter, though: Diaz was able to justify that purchase by 2022 when she sold the home to Ariana Grande for $4.9 million. Quite the jump from the $1.8 million she paid in 2004—plus she gets a pop-star neighbor out of the deal. 

Ashley Benson to Lauren Graham

The LA neighborhood of Los Feliz may be a bit less sleek than further-west enclaves like the Pacific Palisades and Brentwood, but it’s just as star-studded. Gilmore Girls actor Lauren Graham had already owned property in the neighborhood’s gated community Laughlin Park for nearly 20 years when she bought another spot there from Pretty Little Liars star Ashley Benson in 2022. Graham paid $2.7 million for the Spanish-style structure that measures 2,007 square feet across three floors and offers views of the Griffith Park Observatory from its balconies. 

Kate Upton and Justin Verlander to Timothée Chalamet 

Model Kate Upton and baseball player Justin Verlander were only the most recent celebrity owners of this Beverly Hills home when they sold it to actor Timothée Chalamet. Kenny G, Hollywood producer Jon Peters, and tennis player Pete Sampras all previously lived in the four-bedroom, five-bathroom East Coast–traditional–style home. Chalamet paid Kate Upton $11 million for the spot last year, a remarkably steep increase from the $5.3 million the couple paid in 2016.  

Conan O’Brien to Kourtney Kardashian and Travis Barker

Kourtney Kardashian and Travis Barker have made headlines for living separately post-marriage, but if Conan O’Brien’s deal with the couple in late 2022 is any indication, that’s not necessarily their permanent setup. They paid $14.5 million to O’Brien for his Carpinteria, California, home that he paid $7.9 million for in 2015. That’s a steep price tag for a 2,000-square-foot structure, but the home sits directly on the beach and received a top-to-bottom remodel by O’Brien in recent years.

Ashley Tisdale to Madison Beer

AD knows the home that Ashley Tisdale sold to influencer and singer Madison Beer intimately—after all, we toured it just last year. Tisdale redecorated the 1923 build after purchasing it in 2021 for $4.3 million, creating a cozy interior for her family of three out of the 4,434-square-foot home. Just a year and a half after first purchasing the spot, the Tisdale clan had already grown antsy, so they sold it to Beer for $5.9 million.