The Biggest Real Estate Flops of 2009

New-home sales rose 24% and pending home sales jumped 32% in October from a year earlier, but estates with wine cellars, infinity pools and servants' quarters saw their prices drop 7%. Basketball star Shaquille O'Neal and rapper 50 Cent were among the bigger names to take losses or pull their homes off the market.

Some luxury sellers are still weathering the storm. While the former home of the Detroit Lions took perhaps the biggest beating of the year, the former mailing addresses of Leona Helmsley, Nicolas Cage and Bernie Madoff still have no takers. Here are five property duds whose oversized infamy was matched by their inflated price tags:

1. Dunnellen Hall

Location: Greenwich, Conn.
Price: $60 million

When we first wrote about this property in October, the price had been recently slashed from $75 million. That doesn't seem bad until you consider that it hit the market at $125 million last year. Nevermind that Leona Helmsley billed her husband's Manhattan real estate firm for renovations to the estate's 14 bedrooms, two pools, multiple cottages and million-dollar dance floor with funds and later did time for it. This Jacobean manse is a monument to the sluggish luxury home market in Greenwich, where sales during the first nine months of 2009 were down 46% from the same time last year.

2. Nic Cage's homes

Locations: New Orleans; Bel Air, Calif.; Rhode Island; New York; the Bahamas; Bath, England
Price: Roughly $56 million combined

When you're more than $6 million in the red and forced to unload nearly every home you own, suddenly a starring role in The Bad Lieutenant: Port of Call New Orleans doesn't look so bad. Even if it's the business manager's fault, as Cage claims, his homes have been moving like items in a Wal-Mart (WMT) pre-holiday sale -- quickly and cheaply. His two homes in "port of call" New Orleans were appraised at $3.7 million and $3.45 million, but only fetched $4.5 million combined at a foreclosure auction last month. Meanwhile, his Bel Air mansion was on the market for $35 million before its price was dropped to $17.5 million. It sold for an estimated $15 million. His $9 million apartment in New York fetched $7 million, and he still may need to sell his $8 million castle in Bath, his $12 million home in Rhode Island and his $9.49 million home in Las Vegas just to make ends meet.

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