The M​​ost Expensive Celebrity Real Estate Deals of 2021

One star made more than $80 million profit after selling their home!

Celebrities have some of the most stunning homes in the world — and they’re willing to spend a fortune in order to own their dream abode. In 2021, the celebrity real estate market was booming as A-listers made major transactions to both buy and sell their massive estates. For some, that meant parting ways with their Fifth Avenue penthouse while others found their fully renovated dream home in Beverly Hills.

Architectural Digest took a look back at the biggest real estate transactions of the past 12 months to discover which stars made the most expensive moves. From hundreds of acres of land on the Hawaiian islands to an $85 million estate in the Hamptons, these real estate deals will make your jaw drop.

Find out how much these celebs spent on real estate in 2021…

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10. Tommy Hilfiger

Sale: $45 Million

Last year, designer Tommy Hilfiger and his wife Dee Ocleppo parted ways with their European style home in Greenwich, Connecticut for $45 million. The couple say that the home, which was built in 1939, was “in disrepair” when they purchased it a decade ago. Since then, they’ve put massive amounts of work into the 13,344 square foot home with the help of architect Andre Tchelistcheff. The renovations paid off, as Tommy and Dee saw over $10 million in profit with the recent sale.

9. Bette Midler

Sale: $45 million

Bette Midler and her husband Martin von Haselberg lived in their Upper East Side penthouse for over 25 years before putting it on the market in 2019. The 10,000 square foot apartment, which spans three floors, sat on the market for some time before finally being sold in 2021 for a reported $45 million. The 14 room home has sweeping views of Central Park as well as stunning outdoor space that includes multiple terraces, a 900-square-foot garden, and panoramic views of the New York City skyline.

“It’s time for another family to enjoy it,” Bette told the New York Times following the sale.

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8.  Ellen DeGeneres & Portia de Rossi

Sale: $47 million

Ellen DeGeneres and Portia de Rossi have become known for their love of real estate and in 2021, they made several major transactions. In May, the pair sold their 10,000-square-foot Beverly Hills home for a reported $47 million. The couple had purchased the home, which was previously owned by Adam Levine, just two years prior to the sale. The property boasts five bedrooms, 12 bathrooms, a library, and a media room as well as a tennis court and a pool with an accompanying spa.

7. Mark Zuckerberg

Purchase: $53 million

In March, Mark Zuckerberg and his wife Priscilla Chan are said to have dropped $53 million to purchase 600 acres of land on the Hawaiian island of Kauai. The deal came almost seven years after the couple initially purchased 700 acres of space on the island which had a price tag of $100 million. Locals haven’t been pleased with Mark’s purchases, which includes land that was known to have been granted to native Hawaiian families in the mid-1800s. Meanwhile, Mark says the couple aim to protect native wildlife and keep the space open to the public.

“We have been working closely with a number of community partners to promote conservation, produce sustainable agriculture, and protect native wildlife at our ranch and in the surrounding areas, and look forward to extending that effort to Lepeuli in the months ahead,” he said in a statement.

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6. Ellen DeGeneres & Portia de Rossi

Sale: $55 million

In Ellen and Portia’s second major real estate deal of the year, the couple sold off their most expensive property — their Cape-Dutch style estate in Montecito. Ellen and Portia had purchased the mansion just a year prior but the sale brought them over $5 million in profit. The property features five structures across four acres of land, including a 9,000-square-foot main house, a guest house, a detached garage, a pool house, and a barn.

5. Kanye West

Purchase: $57.3 million

Kanye West purchased a $57.3 million home in Malibu in September — and it fits his personality to a tee. The 3,665-square-foot minimalistic mansion is made entirely of concrete and glass and features four bedrooms and four and a half bathrooms. The home, designed by Tadao Ando, was previously on the market for $75 million, but Kanye reportedly got the hefty price cut as part of an off-market deal.

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4. Scooter Braun

Purchase: $65 million

In September, music manager Scooter Braun broke a Brentwood record when he purchased a 19,000-square-foot modern farmhouse for $65 million. The mansion sits on nearly four acres and features six bedrooms, nine and a half bathrooms, an indoor lap pool, steam room, a home theater and wine cellar.

3. The Weeknd

Purchase: $70 million

The Weeknd dropped a cool $70 million on his new 33,000-square-foot estate in Beverly Hills. The house wasn’t even actually for sale until the musician’s real estate agents asked the owners if they could show the property to him. Prior to his purchase, the mansion received a major modern makeover, adding marble throughout and floor-to-ceiling glass sliders. The home also includes a gym, movie theater, music studio, sauna, hammam, and indoor pool. Outside, the estate features a sports court as well as a stunning infinity pool with a waterfall.

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2. Jeff Bezos

Purchase: $78 million

Over the summer, Amazon founder Jeff Bezos and his partner Lauren Sanchez purchased 14 acres of land on Hawaii’s Maui island. The isolated ocean-front land features numerous structures which reportedly includes a 4,500-square-foot main house and a 1,700-square-foot guesthouse. Although it’s unknown exactly how much they spent on the mysterious deal, it’s said that Jeff actually bought out the holding company that owns the land rather than the land itself. Local real estate experts have estimated the deal to have been around $78 million.

1. Calvin Klein

Sale: $85 million

In July, Calvin Klein sold his massive East Hampton property which he had originally purchased back in 1987 for around $3.6 million. The recent sale made Calvin an astounding profit of over $80 million and came by way of a $75 million purchase of the bulk of the estate as well as a $10 million sale of an undeveloped adjacent strip of land.

The historic Hamptons property was built in 1891 by noted architect Joseph Greenleaf Thorp, who famously designed Grey Gardens. The beachfront estate consists of a main house, a pool that was added by Calvin and a boathouse on Georgica Pond.


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