Celebrity real estate is fast paced and cut throat. Over the past 10 years, many of our favorite celebrities have scored incredible pads and lost big in attempted investments.

Oprah Winfrey
Oprah owns a lot of houses. She’s even owned a 2.-bedroom in a small Indiana town. Recently, she bought a high-tech mansion in the box-canyon ski town of Telluride Colorado – complete with a seven-person hot tub and a “wine mine” – for $14 million. She also recently bought an enormous horse farm in Montecito California for $28.8 million.

Ellen DeGeneres
Comedian and host Ellen has been a savage in the real estate market for many years. The funny part is she never intends to sell when buying. “I’ve never bought to sell” she says “I always say ‘this is it I’m never moving.’ People laugh at me now.” She bought this home from fellow flipper Brad Pitt

Nicolas Cage
“Other people own beachfront property; I have ghost-front property,” says Nicolas Cage of owning the most haunted mansion in New Orleans, the Lalaurie house.
He’s called over a dozen other places home throughout the past decade: a castle in Bath, England and a castle-esque residence in Rhode Island which ended up costing him.

Cher
The infamous entertainer found time over the last decade to buy an sell numerous properties, including purchasing a home in the coveted 90210 zip code. She also sold her Hawaiian estate for $8.72 million recently.

Angelina Jolie and Brad Pitt
This power couple has bought at least six homes over the past decade. They recently cut the listing price on the New Orleans mansion they bought in 2006 for the hit movie, “The Curious Case of Benjamin Button” by $850,000.

Julia Roberts
Roberts purchased her main home, in Malibu’s Point Dume, in the early 2000s but that hasn’t kept her out of the real estate game.
She’s asking $26 million for a Hawaiian estate near two other properties she owns. When she dropped the price she raked in $5.35 million on a Greenwich penthouse for which she paid $3.9 million in 2010.
She’s sold homes all over the country including Georgia, the Pacific Palisades, Beverly Hills, Venice California, Tennessee, Massachusetts and Rhode Island.

Dwayne “The Rock” Johnson
The Rock has sold at least ten homes in Florida over the past decade – include his mega-mansion outside Miami which includes two 3-car garages and a deluxe master bath.

Rosie O’Donnell
Her most recent score is a West Palm Beach mansion with 180 feet of waterfront. She paid $5.3 million for it, fully furnished, after having sold her Greenwich Village penthouse for $9 million a couple years ago.

Kelsey Grammer
He’s unloaded many holdings over the years including her main home in Malibu. He has also sold homes in Beverly Hills, Hawaii, The Hamptons and a ski retreat in Colorado.

Reese Witherspoon
For a while, she owned three homes in LA 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.