The 10 Most Expensive Celebrity Real Estate Transactions of 2021

Celebrity Real EstateThe 10 Most Expensive Celebrity Real Estate Transactions of 2021Do you recall who sold their East Hampton estate for a whopping $85 million this year?

By Rachel Davies

December 27, 2021

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Grammy-winning musician The Weeknd purchased this home for $70 million in August.Photo: Berlyn Photography 2021 / Courtesy of The Beverly Hills Estates 

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Whether it’s on the East Coast or West Coast, inland or on the islands of Hawaii, celebrity real estate has been booming all year, with A-listers selling off their old properties and buying up their dream spots no matter the cost. For some, this means letting go of a Beverly Hills midcentury-modern house; for others, snapping up a slice of the Malibu waterfront was in order. Below, AD recalls the most expensive real estate bought and sold by celebrities in 2021.

Tommy Hilfiger, $45 million

Tommy Hilfiger’s castle-like former home.

Photo: Samuel Rodriguez and Steve Rossi for Sotheby’s International Realty

Fashion designer Tommy Hilfiger and wife Dee Ocleppo rang in the new year with the sale of their Greenwich, Connecticut home for $45 million this January. Ocleppo told AD that the European style home was “in disrepair” when they purchased it for $31.4 million in 2010, so it’s safe to say they earned their sizable profit.

Ellen DeGeneres and Portia de Rossi, $45 million

Ellen DeGeneres and Portia de Rossi are known for their love of real estate, and 2021 was no exception. In May, the couple let go of their 10,000-square-foot Beverly Hills home for a reported $45 million. They purchased the property from Adam Levine just two years prior for $42.5 million.

Bette Midler, $45 million

Between indoor space and a landscaped terrace, Bette Midler’s former Upper East Side penthouse measures in at 10,000 square feet—undeniably palatial by New York standards. The entertainer and her husband, Martin von Haselberg, owned the four-bedroom, six-and-a-half-bathroom unit for 25 years before selling it for $45 million, $5 million under their original asking price.

Mark Zuckerberg, $53 million

This March, Mark Zuckerberg and his wife Priscilla Chan spent $53 million on 600 acres of land on the Hawaiian island of Kauai, adding to the 700 acres of space in Kauai that they purchased in 2014 for over $100 million. Locals have been protesting Zuckerberg’s ownership since the original purchase, though the couple claims that they aim to protect native wildlife and keep the space open to the public.

Ellen DeGeneres and Portia de Rossi, $55 million

In late summer, DeGeneres and de Rossi sold off their most expensive property for $55 million, a Cape-Dutch style estate in Montecito that they purchased only a year prior for $49 million. The 4.3-acre property flaunts five structures, including a 9,000-square-foot main house and a barn designed by renowned architect Tom Kundig.

Kanye West, $57.3 million

It’s no secret that Kanye West is a fan of extreme minimalism, and the Malibu home he bought for $57.3 million this September perfectly suits his taste. Designed by Tadao Ando, the 3,665-square-foot home, which is entirely concrete and glass inside and out, features four bedrooms and four and a half bathrooms.

Scooter Braun, $65 million

Pop star manager Scooter Braun broke a Brentwood record in September with the purchase of a $65-million modern farmhouse, the most expensive deal to date in the west L.A. neighborhood. The 19,000-square-foot home’s simple boxy design and natural color scheme allows the space to feel tranquil despite its vastness.

The Weeknd, $70 million

We don’t know how The Weeknd plans to decorate his new pad, but it came with this stylish orange living room.

Photo: Berlyn Photography 2021 / Courtesy of The Beverly HIlls Estates 

Among the most expensive deals in L.A. this year is The Weeknd’s purchase of a $70-million contemporary Bel Air mansion. The roughly 33,000-square-foot estate puts every last inch to good use—it features a gym, a sauna, a movie theater, two pools, and countless other amenities. The home underwent a massive renovation before the musician bought it, leaving it totally modernized with gorgeous marble throughout and floor-to-ceiling glass sliders for seamless indoor-outdoor living. (Branden and Rayni Williams of The Beverly Hills Estates represented the seller, while Angel Salvador of The Beverly Hills Estates represented the buyer.)

Jeff Bezos, $78 million

In a rather mysterious off-market deal, Amazon founder Jeff Bezos and his partner Lauren Sanchez purchased 14 acres of land on Hawaii’s Maui island this June. Though the official price Bezos paid for the property is unknown, local real estate experts have estimated it to be around $78 million. The land’s numerous structures reportedly include a 4,500-square-foot main house and a 1,700-square-foot guesthouse, both of which are Hawaiian plantation style.

Calvin Klein, $85 million

After 34 years with his East Hampton home, fashion mogul Calvin Klein sold the 8.4-acre property for $85 million this July, a full $81.4 million more than he paid for the spot in 1987. A truly historic Hamptons property, the 19th-century home was designed by the same architect as Grey Gardens. The sale included not only the estate, which has a main house, boathouse, and a pool added by the Kleins, but an adjacent valuable strip of land too.

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