10 Most Powerful Celebrity Buyers & Sellers of the Last Decade

Celebrity real estate is a high-paced world of wheeling and dealing. Over the past 10 years, plenty of famous faces have scored big or lost out in attempts to secure (or sell!) the home of their dreams.  To help commemorate its 10th anniversary, Zillow put together this list of some of the hottest homes that have come and gone as these stars vied to scratch their never-ending real estate itch.

By Melissa Allison

Oprah Winfrey

America’s favorite billionaire owns homes all over the country, from Chicago to Nashville to Hawaii. She’s even bought a 2-bedroom in a small Indiana town where she once owned a whole farm.

Recently, the television mogul paid $14 million for a high-tech mansion in the box-canyon ski town of Telluride, Colo. — complete with a seven-person hot tub and a “wine mine” — and $28.85 million at a recent auction for this sprawling horse farm in Montecito, Calif.

Ellen DeGeneres

Beloved comedian and talk-show host Ellen DeGeneres has been buying copious numbers of homes since before she married Portia de Rossi. “I’ve never bought to sell. I always say: 'This is it. I’m never moving.’ People laugh at me now,” she told The New York Times.

DeGeneres bought this Malibu home from fellow house-flipper Brad Pitt.

Nicolas Cage

“Other people own beachfront property; I have ghost-front property,” actor Nicolas Cage said of owning the most haunted mansion in New Orleans, the Lalaurie House.

Not that he limits himself to ghosts. Among the dozen-plus places he’s called home over the past decade are a castle in Bath, England, and a castle-looking home in Rhode Island, which he sold at a 60 percent loss.

Cher

The multi-talented entertainer with seemingly endless energy found time over the past decade to trade real estate, including buying this home in the coveted 90210 ZIP code.

She also auctioned off her Hawaiian estate for a hefty $8.72 million.

Angelina Jolie & Brad Pitt

Here’s a power couple with a powerful appetite for real estate. They’ve bought at least six homes in the past decade and sold one to Ellen DeGeneres. That doesn’t even count the $22.5 million sale of the Beverly Hills home Pitt and ex-wife Jennifer Aniston sold after their split.

Jolie and Pitt recently cut the listing price on the New Orleans mansion they bought in 2006 for Pitt’s Big Easy filming of “The Curious Case of Benjamin Button” by $850,000.

Julia Roberts

Here’s a superstar with a super-long list of homes. Roberts bought her main residence, at Malibu’s Point Dume, in the early 2000s, but has done a fair bit of transacting in the meantime.

She’s asking $26 million for a lush Hawaiian estate that’s near two other Hanalie properties she owns. While she dropped the price on that tropical oasis, Roberts raked in more than she was asking — for a total of $5.35 million — on a Greenwich Village penthouse for which she paid $3.9 million in 2010.

Roberts still has a pad in Manhattan, which she’s reportedly renting out. But she’s unloaded a lot, including homes in her hometown of Smyrna, Ga., and in Pacific Palisades, Beverly Hills and Venice, Calif., the latter to actor Tim Robbins. Across the country, she’s sold homes in Tennessee, Massachusetts and Rhode Island.

Dwayne “The Rock” Johnson

For a guy his size, Dwayne Johnson is surprising nimble — at home trading.

The Rock has leaned mostly toward home selling over the past decade — most of those homes in Florida. He’s unloaded at least 10 homes there over the past decade, including this mega-mansion outside Miami with two 3-car garages and a deluxe master bath.

Rosie O’Donnell

Here’s another talk-show host with a voracious appetite for real estate. O’Donnell’s most recent score is this mansion in West Palm Beach with 180 feet of waterfront.

She paid $5.3 million for it, fully furnished, which shouldn’t be a stretch given the $9 million sale a couple of years ago of her Greenwich Village penthouse.

Kelsey Grammer

While Sideshow Bob was busy being a, well, sideshow on “The Simpsons,” the actor who voices him was center stage in the first season of “The Real Housewives of Beverly Hills,” in which his marriage fell apart — precipitating all sorts of real estate swaps.

The property-loving Grammer unloaded many of his and ex-wife Camille’s holdings in recent years, including their main home in Malibu.

The Grammers also let go of homes in Beverly Hills, Hawaii, The Hamptons and a ski retreat in Colorado.

Reese Witherspoon

For a while, this Oscar winner was a Brentwood fanatic. She bought three homes in the posh Los Angeles enclave, including an “enchanted cottage,” that collectively went for $13.6 million in 2014.

Witherspoon sold her Ojai getaway at a loss, but picked up a $12.7 million Pacific Palisades mansion, along with two homes in Nashville suited to a Southern belle. One of them is a historic home she plans to restore.