It's just a two-hour drive from Miami, but Naples is another world, as famous for its sun-drenched beaches as it is for the high-society snowbirds who fill them. The tony resort town attracts everyone from retired NFL coaches - Mike Ditka has a home here - to former auto execs.
During the real estate boom, Naples regularly landed at the top of housing analysts' overpriced markets lists. But last year a chill fell over this pristine town and its expansive golf courses. Pending condo sales dropped 43 percent from the first quarter to the fourth, and median prices fell 17 percent as buyers chose to wait out the frenzy.
Other scare factors: Florida's soaring insurance costs and a real estate downturn in the Midwest, where many Naples retirees come from. "It even hurt the high end," says Richard Baker, president of luxury condo developer Lutgert. His latest building on Naples's Park Shore Beach, the Aria, still had unsold units after it opened last October. "People were just not buying," he says.
But some experts say the market is starting to stabilize. While there's still excess inventory - a 36-month supply of new condos, plus another 42 months' worth of existing units for sale - construction has halted, and the glut is mostly in the lower end of the market. (Yes, Naples has a low end.) That means now might be the time for the skittish to come off the sidelines.
And buyers may be doing just that: Baker says three $2 million condos sold in the Aria last month. "The savvy second-home buyer is seeing that this is a good time," says Naples Area Board of Realtors President Spencer Haynes. "There's choice now, and they might be able to negotiate a better deal." For this ritzy enclave, that kind of opportunity doesn't come around often.
Is it possible for someone who doesn't run a hedge fund or win the lottery to retire at 50 (or so)? Yes. (more) 
