1. San Francisco

Originally listed: August 2008 for $70 million
Reduced: February 2009 for $49 million
In the penthouse of the St. Regis, across the street from the San Francisco Museum of Modern Art, you'll find 20,000 square feet of space, 2,900 square feet of terraces and views of the entire city through the massive 22-foot floor-to-ceiling windows. The condo includes six bedrooms and eight bathrooms over its two stories of space. Sotheby's International Realty has the listing.
On our blog, 'Listed': Sold ... at a $27.5 million price cut
2. Bridgehampton, N.Y.

Originally listed: August 2008 for $95 million
Reduced: April 2009 for $75 million
Two Trees Farm in Bridgehampton, N.Y., which hosts the annual Mercedes Benz Polo Challenges in the summer, is now asking much less for its 115 acres of land, equestrian facilities and four-bedroom, three-bathroom, 2,500 square foot main house. At present, the Corcoran Group holds the listing.
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more on Forbes.com
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- The 13 most distressed cities of the super-rich
- Where the world's richest live
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3. Southampton, N.Y.

Originally listed: July 2008 for $40 million
Reduced: April 2009 for $20 million
On public sale for the first time since the 1920s, this four-bedroom, two-bathroom home in Southampton, N.Y., has 2,750 square feet of space, 240-feet of ocean frontage and 1.6 acres of space. It's currently listed through Prudential.
4. Washington, D.C.

Originally listed: August 2008 for $30 million
Reduced: March 2009 for $19.5 million
Georgetown is home to many of Washington, D.C.'s most expensive homes, but the sellers of this stately mansion clearly overestimated its worth when it was originally listed for $10.5 million more than its current million-dollar asking price. With views of the Potomac River and Key Bridge, the 18th-century estate is in a prime location and has five bedrooms and nine bathrooms as well as 30,500 square feet of space. It is listed through Sotheby's International Realty.
5. Jupiter Island, Fla.

Originally listed: March 2009 for $39.9 million
Reduced: March 2009 for $29.9 million
The best properties on Jupiter Island, Fla., either have ready access to the island's abundant, world-class golf courses, or have unbelievable lengths of oceanfront. In this latter case mansion, there are 428 feet of shorefront, not to mention a tennis court, home gym, nine bedrooms and 12 bathrooms across an epic 17,500 square feet.
