Best and Worst Celebrity Real Estate Deals 2009

Celebrity Real Estates Winners and Losers

After looking at just about every house in Los Angeles listed at more than $15 million, Ben Affleck and Jennifer Garner finally decided on a perfectly private Cliff May-designed compound in Pacific Palisades, California that they bought from super producer Brian Grazer in the spring of 2009. Originally listed at $24.5 million, Affleck and Garner scooped up the 8,798 square foot single story sprawler for 30 percent less than the asking price, paying $17 million for the 5 bedroom and 8 bathroom house.

Celebrity Real Estates Winners and Losers

Without question, the award for the farthest fall off the real estate mountain in 2009 goes to Academy Award winning actor Nic Cage. At its apex, Cage's notoriously voracious appetite for high-end properties left him with more than 12 posh properties around the world and tens of millions of dollars in mortgages. Beginning in early 2008, he began his great real estate sell off when he unloaded a waterfront mansion in Newport Beach, California for around $35 million. He's subsequently managed to lighten his portfolio by successfully off-loading a castle in Bavaria, another castle in the U.K., a gorgeous Georgian style townhouse in Bath (UK) and a couple of combined condos in New York City.

Celebrity Real Estates Winners and Losers

Even with all the foreclosure fracas and bargain hunters and bottom feeders looking for major deals, there were a few celebs holding real estate rabbit's feet who managed to squeak out tidy profits in 2009. Actor Ashton Kutcher, who now lives with his May/December lady-friend Demi Moore, paid $1.69 million for his Beverly Hills bachelor pad back in May of 2001. The young Hollywood power player sold the 6 bedroom and 6.5 bathroom house in early 2009 for $3.67 million, lining his pockets with an almost $2 million profit.

Celebrity Real Estates Winners and Losers

An A-lister who has had a serious real estate reality check in 2009 is comedian Eddie Murphy. About five years ago, Murphy listed his massive New Jersey mansion known as Bubble Hill with an asking price of $30 million. Several subsequent price chops have brought the current asking price for the 25,000 square foot, 8-bedroom and 9 full and 4 half-bathroom mansion all the way down to $14.99 million, just under half the original price tag. The lavish-living Murphy has also had to reduce the asking price of Clove Hill Farm, his 205-acre spread in upstate New York, from $8.995 million to $5.995 million.

Celebrity Real Estates Winners and Losers

Prolific property buyer and seller Ellen Degeneres picked up a $10 million ranch in suburban Los Angeles.

Celebrity Real Estates Winners and Losers

Many celebs got caught between the rock and the hard place created by a desperate economy and shrinking success. One of those poor fellows was pop rock musician Ryan Cabrera. In the fall of 2006 the young singer spent $1.45 million on a 3-bedroom and 3-bathroom house in Hollywood Hills. Fast forward to August of 2008 when Cabrera listed the mock Mediterranean mini-manse with an asking price of $1.699 million. More than a year later, the house remains for sale at $1.1 million, representing a loss of at least $350,000. Will he and his hard working real estate people pull a real estate rabbit out of a hat and find a buyer willing to pay full price for the property?

Celebrity Real Estates Winners and Losers

Despite the real estate market swirling down the toilet in 2009, there were still a few filthy rich folks who spent big, big, big on high-ticket residences. Madonna paid $25 million for a 12,000 square foot, 13-bedroom and 12+ bathroom triple wide townhouse on the Upper East Side of Manhattan.

Celebrity Real Estates Winners and Losers

Miami, the sunny wintertime playground of the rich and famous, was hit particularly hard in by the recent burst of the real estate bubble. Back in 2004, too tall dribbler Shaquille O'Neal purchased a 19,440 square foot house on star studded Star Island. Less than a year later he flipped the boutique hotel-sized waterfront mansion back on the market with an asking price of $32 million. Eventually the price jumped to $35 million and there were rampant rumors that Alex Rodriguez was looking to buy the 8-bedroom and 11-bathroom beast. But alas, according to property records, in June of 2009, Shaq and Mrs. Shaq finally sold the house for just $16 million. While that is a toe-curling amount of money to most people, it's a staggering $19 million less than the O'Neals had hoped to sell the mansion -- and a gut wrenching $2.8 million less than they paid. Ouch! That surely stings like a thousand bees no matter how fat the bank accounts might be.

Celebrity Real Estates Winners and Losers

Comedian and daytime talk show queen Whoopi Goldberg also figured out a way to buy at the peak of the market and sell at the low point for a fat profit. The dreadlocked Oscar winner picked up a 3,600 square foot loft in New York City's SoHo neighborhood in October of 2006 for $1.648 million and listed the 2-bedroom and 2.5-bathroom condo for sale in August of 2009 for $3.99 million. The real estate gods were shining on Ms. Whoopie in 2009 because recent reports indicate she is in contract to sell the loft for around $3.6 million, which would more than double her money. Go Whoopie! Go Whoopie!

Celebrity Real Estates Winners and Losers

Among those who did have their homes taken by the bank this year: La Toya Jackson lost a condo in Las Vegas, former professional baseballer Lenny Dykstra lost a massive mansion in suburban Los Angeles, music producer Scott Storch went down in spectacular style losing a $10 million mansion in Miami, Los Angeles property developer Robert Bisno had his $22 million mansion in Beverly Hills snatched away by the bank and Baldwin brother Stephen was relieved of his mortgage responsibilities on his Rockland County, New York residence.

Celebrity Real Estates Winners and Losers