25 Times Celebrities Sold Homes to Each Other

Location: Beverly Hills, California
Estimated Cost: $6.4 Million*

After 13 years, in the Beverly Hills home that she bought from Ellen DeGeneres in 2001, Jessica Simpson flipped the 5-bedroom 5,500-square-foot relatively quaint mansion, and sold it to yet another A-list celeb, the star of the Hunger Games series, Jennifer Lawrence, for $6.4 million.

Jessica Simpson to Jennifer Lawrence @lonnymag/Pinterest | ©Featureflash Photo Agency/Shutterstock.com

As one would probably have guessed, the master bedroom in the house that J-Law purchased from the pop star/reality star has a massive walk-in closet. The house is surrounded by trees to give optimum privacy, and the yard has an in-ground swimming pool and courtyard that, with its stone walkway, koi pond, and ivy lining, looks like something out of a fairy tale.

Location: Los Feliz, California
Estimated Cost: $6.37 Million*

The “Seyler House” is one of the handfuls of estates that holds the honor of being a multi-generational celebrity home. The 4,026-square-foot residence has switched hands several times, belonging to the likes of Kareem Abdul-Jabber, E.R.’s Noah Wyle, Tim Curry (Rocky Horror Picture Show), Robert Pattinson, and Jim Parsons, who purchased it back in 2014.

Robert Pattinson to Jim Parsons @TMZ_News/Pinterest | ©Kathy Hutchins/©DFree/Shutterstock.com

The mansion’s lagoon-style swimming pool probably had something to do with Parson’s decision to drop $6.37 million on Pattinson’s former Los Feliz residence. Or, perhaps it was the home library inside the 3-bed, 3-bath house that caught Sheldon’s attention. Either way, it wasn’t for very long, because in 2018 he listed the “Seyler House” for $9 million.

Location: The Hamptons, New York
Estimated Cost: $36 Million*

The estate that the host of the Today show Matt Lauer took off of Richard Gere’s hands in 2016, or the Strongheart Manor as it’s known, is not your average celebrity home. It’s much, much bigger! The property has 12 bedrooms, 12 bathrooms, a basketball court, and a small “island-inspired tea house” that can be found just off-shore in the mansion’s private pond.

Richhard Gere to Matt Lauer @archdigest/Pinterest | ©lucacavallari/Shutterstock.com

Originally listed for a reported $65 million, Lauer got himself a steal – paying “only” $36 million for Richard Gere’s former pad in the Hamptons. Not even 3 years later Matt Lauer put the 14,000-square-foot home and the 6.3-acre property that it sits on up for sale – with a listing fee of $44 million.

Location: Calabasas, California
Estimated Cost: $7.2 Million*

The 9,214-square-foot Spanish-style Calabasas mansion that Khloe Kardashian bought off of “the Biebs” comes fully equipped with everything someone would need if they were planning on entertaining guests of the highest quality. A 200-bottle wine cellar, spa, swimming pool, and even a guest “casita”.

Justin Bieber to Khloe Kardashian ©Dimitrios Kambouris / Gettyimages.com @KhloeKardashianFansForever/Facebook

During the cool Californian winter nights, Khloe and her family needn’t worry about catching a chill, because their new mansion has 6 fireplaces to keep them warm – and there would have been plenty of wood to feed the fires from Bieber’s old skate ramp that the youngest Kardashian sister would have, most likely, had dismantled.

Location: Beverly Hills, California
Estimated Cost: $8.55 Million*

We’ve all heard the stories of what used to happen at the parties Charlie Sheen had held at his homes, but few people knew much of what the inside of his party pad was like. It has 5 bedrooms and 6 bathrooms, a movie theater, and a huge outdoor fountain. Pretty much, it’s everything you thought it was.

Charlie Sheen to Kendall Jenner @teenvogue/Pinterest | ©Joe Seer/©DFree / Shutterstock.com

Apparently, it was everything that Kendall Jenner thought it was as well, because in 2017, after moving out of the place she had bought from The Office’s John Krasinski, Jenner bought Sheen’s Spanish-style 6,625-square-foot Beverly Hills mansion – on which she spent $8.55 million.

Location: Los Feliz, California
Estimated Cost: $7.1 Million*

The Spanish Colonial house that Modern Family’s Jesse Tyler Ferguson and his husband Justin Mikita purchased in 2013 for $4.6 million, they sold last year (2021) to Leo for $7.1 million – making themselves a nice profit. The house that DiCaprio bought is on arguably the best street in the neighborhood, however, if history repeats itself Leo won’t be living there.

Jesse Tyler Ferguson to Leonardo DiCaprio @teenvogue/Pinterest | ©DFree/©taniavolobueva/Shutterstock.com

The last time Leonardo DiCaprio bought a home in Los Feliz it was for his father. In fairness, if given the opportunity, who wouldn’t want to move their whole family to one of the best neighborhoods on the western seaboard?

Location: Brentwood, California
Estimated Cost: $40 Million*

It’s not very often that legends of different industries cross paths and buy homes from each other, however, that’s what happened in 2014 when Dr. Dre bought Tom Brady’s 18,298-square-foot Brentwood estate. For most celebrities, the price tag would probably have been too high to even consider, but not for Dre who had no problem shelling out $40 million for the home (or the equivalence of Tom Brady’s annual salary).

Tom Brady and Gisele Bündchen to Dr. Dre @modernmansions/Instagram | ©Everett Collection/©Kathy Hutchins/Shutterstock.com

Located in a quiet upscale area in L.A.’s westside, the home boasts a beautiful garden (with waterfalls), seven fireplaces, 5 bedrooms, 9 bathrooms, a library, a sauna, a gym, and, if that wasn’t enough, an infinity pool as well.

Location: Montecito, California
Estimated Cost: $6.85 Million*

Some celebrities buy their homes to later sell them at a higher price. Academy Award winner Jeff Bridges is not one of them. When the Bridges bought their Montecito home in 2014, they paid $6.85 million for it – the same price tag the house had when they sold it to Oprah 4 years later.

Jeff Bridges to Oprah Winfrey @people/Pinterest | ©DFree/©Cubankite/Shutterstock.com

Built in 1919, the 3,517-square-foot Spanish revival-style home was on Oprah’s radar soon after it hit the market. Buying this 2-bed, 3-bath estate was a no-brainer for Winfrey who was already the owner of a few other modest mansions in the area.

Location: Miami, Florida
Estimated Cost: $3.5 Million*

Professional athletes are some of the highest-earning individuals on the planet, and a number of them let their wealth be known by spending outrageous amounts of money on houses that are so big that they rarely visit most of the property. When their professional careers are over, however, without the 7 or 8 figure annual income that they’re used to, most end up selling their extravagant homes.

Amar’e Stoudemire to Rick Ross @amluxmag/Pinterest | ©Kathy Hutchins/©Jamie Lamor Thompson/Shutterstock.com

In 2021, the Miami-based rapper, Rick Ross, bought former NBA all-star Amar’e Stoudemire’s 6-bedroom, 7-washroom Miami mansion, that lies on a 2.3-acre piece of land, for $3.5 million – $200,000 less than Amar’e paid for it 10 years prior. 

Location: Tarzana, California
Estimated Cost: $3.45 Million*

In her post-Disney life, Selena Gomez has taken to flipping her homes to other celebrities. In 2015, Gomez made headlines when she sold her Calabasas estate to French Montana for $3.3 million, but a year earlier, the former Disney star sold another of her homes to Iggy Azalea and Nick Young.

Selena Gomez to Iggy Azaela @georgiapapadon/Pinterest | ©Featureflash Photo Agency/Shutterstock.com

In 2014, the couple paid $3.45 million for Gomez’s 6,630-square-foot 6-bedroom, 7.5-bathroom Tarzana mansion. The private guesthouse is fully equipped with a kitchen, living space, and washroom, while the main house has a wraparound balcony that’s accessible from most of the room on the one-floor estate.

Location: Hollywood Hills, California
Estimated Cost: $6.5 Million*

The Kardashian/Jenner clan are no strangers to buying homes from (or selling their homes to) other celebrities, and in 2015, Kendall Jenner joined the A-list house swapping party when she bought John Krasinski and Emily Blunt’s 4,800-square-foot home in the Hollywood Hills for $6.5 million.

John Krasinski and Emily Blunt to Kendall Jenner @zillow/Pinterest | ©s_bukley/Shutterstock.com

As a result of privacy and security problems she was having, approximately a year after moving into the 6-bed, 5-bath estate next to funnyman Jimmy Kimmel, Jenner put the house back on the market and moved out of the neighborhood.

Location: Beverly Hills, California
Estimated Cost: $35,000/Month*

The 10,337-square-foot Beverly Hills home that once belonged to “Ol’ Blue Eyes” Frank Sinatra was taken down more than a decade ago, however, a modernized mansion that would have made the “Sultan of Swoon” proud was erected in its place.

Frank Sinatra to Nicki Minaj @normandinone/Pinterest | ©mark reinstein/©Kathy Hutchins/Shutterstock.com

The new home was built in 2008, and has one of the most unique features that we’ll find amongst any of these celebrity homes – a two-story front foyer with a floating staircase. If that’s not enough to get your juices going, this $35,000/month property also boasts a magnificent view of the Hollywood Hills.

Location: Beverly Hills, California
Estimated Cost: $10 Million*

Before Nicole Richie even knew that she wanted to sell her Beverly Hills digs, Adele had already made her an offer. This might sound a little odd, but it’s not as strange as you’d think. The reason Adele knew that she wanted Richie’s home was that she already knew the area as a result of owning the house across the street. 

Nicole Richie to Adele ©Kathy Hutchins/©Featureflash Photo Agency/Shutterstock.com

No, Adele was not looking to live in 2 houses simultaneously. House opposite her new purchase, although owned by the songstress, is reportedly occupied by her ex-husband. Adele ended up paying $10 million for Richie’s home, and Nicole didn’t have to deal with any of the hassle involved in listing the home or having it shown.

Location: Hidden Hills, California
Estimated Cost: $19.3 Million*

The Weeknd’s Hidden Hills home was not on the market for very long when a buyer came by and scooped up the place. And how could we blame them? It’s a 12,500-square-foot mansion on almost 3 acres of land with a fitness center, home spa, theater, basketball court, swimming pool, and guest house.

The Weeknd to Madonna @marckrueger79/Pinterest | ©Ovidiu Hrubaru/©Denis Makarenko/Shutterstock.com

In 2021, adding to her collection of homes, none other than the Queen of Pop herself, Madonna, purchased The Weeknd’s 7-bedroom, 9.5 bathroom California home for $19.3 million. $20 million might seem like a lot to pay for a holiday home, however, when you’re Madonna it’s more like pocket change – besides, she did get a $3 million discount.