1. BURR RIDGE
Sale Price: $1 million
This 13-room house in a pricey gated subdivision went on the market in March 2007 priced at $1,469,900. “[The seller] wanted to get back the $1.4 million he had in it,” according to his real-estate agent, Bobbie Limjuco of @properties. “In a good market, we could have gotten about $1.3 million for it.” (DuPage County records do not indicate how much the seller paid for the place when he bought it in July 2005.) The seven-year-old house lingered on the market until January, by which time its asking price was $1,275,000 and the seller, says Limjuco, was “in financial distress.” Some buyers finally scooped up the place in early February. “They walked away with the best deal in the whole subdivision,” says Limjuco. “When the market goes back up, they’re going to make a bundle on that house.”

2. VERNON HILLS
Sale Price: $875,000
“They stole that house,” says Baird & Warner’s Patti Warsaski, referring to the recent buyers of a 13-room home in the Gregg’s Landing subdivision in Vernon Hills. In June 2007, Warsaski had priced the house at $1.25 million, two months before a slightly larger place down the block sold for $1.3 million. Lots of people toured this residence, but it sat unsold into 2008. “The market was going down, and we kept marking the house down to stay with the market,” Warsaski says. She got several rock-bottom offers—as low as $725,000—but nothing that the sellers of the three-year-old house could stomach. “We had to get very aggressive about selling and take whatever offers we could get,” says Warsaski. The ultimate sale price was 30 percent below the original asking price—”a heck of a deal for the buyer,” says Warsaski.

3. BRONZEVILLE 
Sale Price: $560,000
This 119-year-old graystone on a corner lot was sold in March for nearly 20 percent less than the sellers had paid for it in June 2005. Even with an incomplete kitchen rehab, some roof leakage, and evidence of termites, the 6,000-square-foot house was appraised last fall for $750,000. Kimberly Chase-Harding, the Coldwell Banker agent who represented the sellers in their short sale—a bank-sanctioned strategy that avoids the hassles of foreclosure by letting a property be sold for less than its total mortgage debt—estimates that it would cost about $60,000 to finish the kitchen and otherwise make the house livable. That investment would still keep the buyers’ total costs at 10 percent below the house’s 2005 sale price of $689,000.

4. BUCKTOWN
Sale Price: $909,000
After buying this nine-room house for $875,000 in May 2006, the owner spent about $150,000 on upgrades, including decorating three baths with marble. But by spring 2007 he was overextended and had the house back on the market, for $1,075,000. “He needed $1,025,000 to satisfy the bank and brokerage fees,” says Patrick Hawkins, the Property Consultants agent who represented the seller. “It came to the point where that was not going to be feasible.” This past winter, the owner’s bank gave him until February 18th to sell the house or be foreclosed. Hawkins slashed the price to $899,000, which was the bank’s absolute minimum. “I have never fielded so many phone calls in my life,” says Hawkins.

5. NEAR NORTH
Sale Price: $865,000
The sellers of a three-bedroom condo on the 30th floor of the Bristol (at Delaware and Rush streets) had paid $1,060,000 for the place in April 2003. When they put it on the market last September for $1 million, they seemed to acknowledge that the market had passed its peak. They later cut the asking price even more—to $920,000. By the time they sold the 2,015-square-foot condo in March, the price they got was a full 18.3 percent below their original purchase price. The new owners can fully savor their Lake Michigan views knowing they likely pocketed nearly $200,000 in savings.

6. OLD TOWN
Sale Price: $812,500
The seller of this 1880 brick house had lived there for more than 15 years and was ready for a change. So when she was told by a real-estate agent in May 2005 that her house would probably fetch about $1.3 million, she started looking for a new home. Eventually she settled on a condo in a new downtown building that would be ready in late 2007. But last summer her house was still unsold, even though successive price cuts had brought the asking price down to $950,000. In September, with just six weeks until she was supposed to close on the new place, the seller told Janice Smith—her third agent—that she couldn’t afford to carry both properties. Smith, the president of J. A. Smith & Associates (which recently merged with @properties), cut the asking price to $895,000—or 37 percent below the first agent’s misbegotten estimated sale price.

Photography: (1 and 2) Chris Guillen, (3 and 4) Kim Thornton (5) Kim Thornton, (6) Dennis Rodkin