When it comes to celebrity homes, everyone knows they’re massive and worth millions (if not hundreds of millions). So, knowing how much money it costs to own one, it’s no wonder that some celeb mansions, like Ariana Grande’s former Tudor Style home or The Weeknd’s former Hidden Hills mansion, were passed from one celebrity to another.
And though some of these buyer-seller duos (and even trios!) likely knew each other before the sale, like Oprah Winfrey and Jennifer Aniston, or Khloé Kardashian and Justin Bieber, it’s interesting to see how two celebrities with different lives, styles, and careers shared the same exact home in different times. Leonardo DiCaprio and Jesse Tyler Ferguson, or Kendall Jenner and Charlie Sheen, for instance, are other prime examples.
So, to find out which of your favorite celebrities have bought or sold their homes to other familiar names, scroll on! And, P.S., Don’t be surprised if a few names pop up more than once – celebs have the money to accrue a whole real estate portfolio if they want to!
Khloé Kardashian & Justin Bieber
Back in 2014, Khloé Kardashian bought a Tuscan villa-style mansion from Justin Bieber for $7.2 million. Since acquiring the property, the Good American co-founder did a total Kardashian renovation to make the place her own. Six years later, in 2020, The Kardashians star made a huge profit by selling the 9,320-square-foot house to YouTube sensation Dhar Mann for $15.5 million.
Rihanna & Chrissy Teigen and John Legend
Who wouldn’t want a home once owned by Rihanna? Chrissy Teigen and John Legend did just that back in 2016 when they bought the “Love on the Brain” singer’s Beverly Hills home for $14.1 million. After Teigen got pregnant with their late son Jack, however, the couple listed the home for $24 million in 2020. A year later, they sold it for $16.8 million.
Selena Gomez & French Montana
After two years in her luxurious Calabasas mansion, Only Murders in the Building star Selena Gomez sold her place to rapper French Montana for $3.3 million in 2016. In 2020, following some major upgrades including a $400,000 recording studio, the “Ain’t Worried About Nothin” rapper sold the home for a profit at $5 million.
Madonna & The Weeknd
Back in 2021, Abel ‘The Weeknd’ Tesfaye’s former Hidden Hills home made history when the Queen of Pop, Madonna, bought the place and became the second-ever owner of the home to perform at the Super Bowl. Impressive right? The “Like a Virgin” singer bought the 13,391-square-foot home for $19.3 million. Four years earlier, in 2017, Tesfaye bought the place brand new for slightly more at $20 million.
Cameron Diaz & Ariana Grande
In 2022, Cameron Diaz made a significant profit when she sold her Hollywood Hills home to none other than upcoming Wicked star Ariana Grande for $4.9 million. Almost two decades earlier, in 2004, Diaz paid $1.8 million for the property. Talk about a good deal!
Conan O’Brian & Kourtney Kardashian and Travis Barker
After their star-studded Italian wedding, lovebirds Kourtney Kardashian and Travis Barker bought their first home together. And, as it turns out, the 2,000-square-foot structure in Carpinteria, California, worth $14.5 million, was owned by former talk show host Conan O’Brien.
Timothée Chalamet & Kate Upton and Justin Verlander
In 2022, Call Me By Your Name star Timothée Chalamet paid a whopping $11 million for Kate Upton and baseball player Justin Verlander’s home in Beverly Hills. Fun fact: before Upton and Verlander, the property also once belonged to Kenny G, Hollywood producer Jon Peters, and tennis player Pete Sampras. Talk about star-studded!
Adele & Sylvester Stallone
Although Sylvester Stallone originally listed his massive Beverly Hills home for $110 million, Adele ended up snagging the place after some price drops and made it hers for $58 million. It seems like not even Rocky could resist the singer’s charms.
Adele & Nicole Richie
Speaking of the singer, Adele also purchased another home, a Beverly Hills mansion with four beds and four baths, from her next-door neighbor Nicole Richie back in 2021. The “I Drink Wine” singer bought the pad for $10 million, much more than the $6.7 million Richie and her husband Joel Madden paid in 2015.
Oprah Winfrey & Jennifer Aniston
Last year, Jennifer Aniston walked away with Oprah Winfrey’s Mediterranean-style villa for $14.8 million. Now they’re all Meghan Markle and Prince Harry’s neighbors!
Jesse Tyler Ferguson & Leonardo DiCaprio
From Modern Family to Titanic! In May 2021, Leonardo DiCaprio snagged Jesse Tyler Ferguson’s Spanish Colonial–style home in Los Feliz, California, for $7.1 million. Ferguson, and his husband Justin Mikita, first bought the home in 2013 for $4.6 million thoroughly renovated it since.
Ellen DeGeneres & Ariana Grande
Some celebrity purchases, especially when it comes to Ellen DeGeneres, might not be for living and aim to just make a profit instead. For example, in early 2021, the former daytime talk show host bought a Tudor-style home in Montecito, California, for $3.6 million only to sell it to Ariana Grande a few months later for $6.75 million. Talk about a worthy investment!
Jennifer Garner and Ben Affleck & Adam Levine and Behati Prinsloo
From one Hollywood duo to another! Years after they announced their divorce in 2015, Jennifer Garner and Ben Affleck found a buyer for their massive Pacific Palisades home in 2019: Maroon 5 frontman Adam Levine and his wife Behati Prinsloo. For the property, which includes a ranch-style main residence and two other structures, Levine and Prinsloo paid $32 million.
Ellen DeGeneres & Adam Levine and Behati Prinsloo
Speaking of the couple, the two also balanced out their finances that year by selling a five-bedroom Tudor-style Beverly Hills home to Ellen DeGeneres for $45 million.
Kendall Jenner & Charlie Sheen
Back in late 2017, supermodel and reality star Kendall Jenner bought her sprawling Beverly Hills home from none other than Two and a Half Men actor Charlie Sheen. According to Architectural Digest, however, the model had big plans to renovate and redecorate her new home.
Emily Blunt and John Krasinski & Kendall Jenner
In addition to Sheen’s pad, Jenner also bought John Krasinski and Emily Blunt’s West Hollywood home back in 2016 for $6.5 million. Her stay, however, didn’t last long as problems with security, including stalkers and burglars, led her to list the property back on the market in 2017, per House Beautiful. She eventually sold it for a profit at $6.85 million.
Kate Winslet & Chris Martin and Gwyneth Paltrow
When they were still together, former couple Chris Martin and Gwyneth Paltrow alternated between living in London and in California. Their English residence just so happened to be the former home of Kate Winslet, who sold the Belsize Park place to the couple for $4.1 million.
Lenny Kravitz & Alicia Keys and Swizz Beatz
Speaking of Hollywood power couples, Alicia Keys and her husband Swizz Beatz bought Lenny Kravitz’s former New York City apartment for $14.5 million back in 2010.
Alexander Skarsgård, Rooney Mara & Kelly Osbourne
In 2015, actress Rooney Mara bought the 2,340-square-foot midcentury-style home from Big Little Lies star Alexander Skarsgård for $2.9 million. Two years later, she put the property back on the market and found a buyer in none other than Kelly Osbourne for $3.58 million.
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