This has little to do with the housing market broadly speaking: In cities like New York, San Francisco, and Boston, prices are rising and homes are sold within days of listing. Rather, it’s a sign that suburban neighborhoods straight out of Mad Men are no longer as in-demand as they once were. Around Boston, for example, 51 towns and suburbs started the year with price declines while the city’s prices skyrocketed. Indeed, as Blackwood drives me through this picturesque New England town just an hour from New York, we pass dozens of for-sale and for-rent signs outside home set back from the road. These are homes that, one day, might have been on any family’s dream list, back when suburbs were where everyone wanted to live and there were dozens of companies to work for nearby. Median home values in Fairfield County, where New Canaan is located, are down 21 percent from their peak in 2003, according to Zillow; for the state as a whole median home values are down 18 percent from their 2004 peak. By contrast, home values nationwide are down just 5 percent from their 2005 peak. In urban areas, they are up—often substantially; in Boston, Charlotte, Portland, San Francisco, and Seattle, prices this year have set record highs.

Cities are in vogue again, and that’s starting to be a problem for places that are made up mostly of suburbs. Companies like General Electric that were once headquartered here in the suburbs are decamping for city centers, where they say they can more easily find the talent they need. In 2010, Aetna abandoned a giant campus in Middletown, Connecticut; Pfizer recently tore down 750,000 square feet of unused laboratory space in nearby Groton. At the same time, the baby boomers who flooded the suburbs to raise their children are getting older and no longer need big homes, but their children’s generation doesn’t have the desire—nevermind the savings—to buy up the houses, at least not at the prices boomers are looking for.

The Northeast has long been growing more slowly than other, warmer, parts of the country. Now, parts of the region are starting to see net losses in population. Between 2014 and 2015, Connecticut lost nearly 4,000 residents as Florida, a retirement hub, added 366,000. During that same period, the Northeast and Midwest together lost half a million people to the South and West. “Where the real action is is the Sun Belt,” William Frey, a demographer with the Brookings Institute, told me.

The losses are exacerbated by the fact that the region’s median age is growing. Connecticut, alongside New England neighbors Maine, New Hampshire, and Vermont, is one of only a few states to have a median age over 40, which means half of its population is over child-bearing age, according to Peter Francese, a New Hampshire-based demographer. “Connecticut is a basketcase demographically, as are many of the states in New England,” Francese told me.