When checking out the highest-priced home sales in the Chicago area, the two suburbs where I most often wind up are Lake Forest and Winnetka. While other towns (Hinsdale, Kenilworth, Glencoe) have lots of high-end sales, these two towns are perennially near the top of Chicago’s rankings for the number of sales at a million dollars or more (usually behind Chicago’s Gold Coast and Lincoln Park neighborhoods).

The two towns are roughly comparable: they have long histories of affluence, great schools, gorgeous housing both old and new, and superb beaches. But they seem to be responding differently to the steep downslide in the real-estate market. The village of Winnetka, which is considerably smaller than the city of Lake Forest, has seen more homes sell than its northern counterpart. According to Midwest Real Estate Data, Winnetka, with 38 percent fewer households than Lake Forest, had 40 percent more sales of $1 million–plus homes from November 2008 through January 2009. The numbers are small—ten sales in Lake Forest and 14 in Winnetka—but nevertheless completely out of proportion to the towns’ sizes

“Sellers have brought their prices way down in Winnetka; we’ve all concluded that sellers in Lake Forest have not adjusted like those in Winnetka have,” says Adele Bensinger Curtis, a Prudential Preferred Properties Agent in Lake Forest who also has covered Winnetka extensively in her 26 years selling North Shore real estate. “They’re not compensating for the fact that they are in a dismal market. In Winnetka, Wilmette, the southern part of the North Shore—they’ve gotten it. They understand we’re not in 2005 anymore.”

Curtis’s own research shows that, as of early February, the number of homes listed for sale in the two towns was proportional to their populations: Winnetka has a little more than 60 percent of Lake Forest’s population and its number of listed homes. Despite that, over the past six months Winnetka has had 20 percent more home sales than Lake Forest (those are sales at all price levels, not just the $1 million–plus range).

Curtis speculates that, because Winnetka is closer to Chicago, its residents might have a better grasp of the problems plaguing the larger real-estate market—and so they are willing to drop their prices if that’s what it takes to sell their homes. But she also says that the imbalance between Winnetka and Lake Forest looks likely to change. “[The price drops] are progressing up the North Shore,” she says. “It has always been like that, for 25 years. The trends work their way up the North Shore. I think things are happening that indicate to [Lake Forest home sellers] that prices need to come down. Read the papers; listen to the news. Hello.”