BOSTON ( TheStreet) -- The high-end real estate market hit new lows this year as multimillion-dollar properties failed to attract buyers even after huge discounts.

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:

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.

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.

Emerald Caye

Location: Turks and Caicos

Price: $48.5 million

As shaky as the luxury housing's foundation is, it's firm bedrock compared to the drowning private island market. This 30,000-square-foot property on 2.32 acres of island accessible only by a remote-controlled swing bridge was on the market for $75 million last year, but cut its price 35%. As tough as it must have been to discount a three-story library, 6,000 bottle wine cellar, home theater, fitness room, two swimming pools, tennis and volleyball courts, two boat slips and two guesthouses, that's just the way things have been for private island sellers this year.

Nick Hexum of reggae-rock band 311 put his 5.5-acre island in the Florida Keys on the market for $10 million in 2006, but cut the price to $3.85 million this year. The still unsold 1,235-acre Nafsika Island in Greece's Ionian Sea was offered by the Onassis family for more than $21 million before its price was cut in half.

Any Bernie Madoff home

Locations: The Hamptons, Manhattan and Palm Beach, Fla.

Prices: $9.4 million, $8.9 million and $7.9 million

Unlike Cage, Madoff is at least assured a home once all his property is sold. From the cozy confines of his federal prison cell in Butner, N.C., Madoff watched as his creditors got $9.41 million from the sale of his Montauk, N.Y., home in October. That was more than the $8.75 million asking price, but it falls short of repaying the $65 billion he took (never mind the more than $21 billion in investor losses).

Madoff's 4,000-square-foot condo in an Upper East Side co-op has been reduced from $9.9 million to $8.9 million, while the 8,700-square-foot Palm Beach house Madoff valued at $11 million was offered for $8.49 million before dropping to $7.9 million.

The Pontiac Silverdome

Location: Pontiac, Mich.

Price: $583,000

When Hulk Hogan bodyslammed Andre the Giant here during Wrestlemania III in 1987, it probably didn't hurt nearly as much as the stadium's selling price hurt Pontiac. The enclosed stadium, the home of the Detroit Lions and Pistons, cost $55.7 million to build before opening in 1975. Adjusted for inflation, that would be $220 million today.

With all due respect to Michigan's struggles with the auto industry, a used car salesman would make more selling a 1975 AMC Gremlin than the 1% return Pontiac got when a Canadian developer won the Silverdome auction with a $583,000 bid last month. This was the home of Super Bowl XVI.

-- Reported by Jason Notte in Boston.

Jason Notte is a reporter for TheStreet.com. His writing has appeared in The New York Times, The Huffington Post, Esquire.com, Time Out New York, The Boston Herald, The Boston Phoenix, Metro newspaper and the Colorado Springs Independent.