Best Old House Neighborhoods 2011: The South

It's said that you need to be either a poet or loco to live in Old San Juan, where Old World charm meets decidedly New World eclecticism. Packed into the winding streets of this fortified Caribbean peninsula are artists, students from three universities, shop owners, café culture knockabouts, lawyers, musicians, millionaires, government employees, and the gobierno himself, who lives in La Fortaleza; built in 1540, it's the longest-occupied governor's mansion in the Western Hemisphere. Neighbors chat over café con leche at places like La Bombonera every morning, and a walk on the blue-gray cobblestones, called adoquines, leads past impeccable, colorful Spanish Colonial rowhouses on par with those of Madrid.

The Houses
Restoring a Spanish Colonial, with its 2-foot-thick walls, brick-lined cisterns, and lead-pipe plumbing, is a long, involved process that is strictly overseen by the Instituto de Cultura Puertoriqueña. "They have a say inside and out, down to the hinges," says Realtor Margarita Gandía, whose mother was one of San Juan's first Realtors in the 1950s. A shell might go for $300,000. Homes requiring less than a gut-renovation can command $600,000. Finished, properties are worth $1 million or more.

Why Buy Here?
The upside to following strict preservation guidelines is that if the result passes inspection, you'll pay nothing in property taxes. That status has to be renewed every 10 years, under inspection, which keeps the neighborhood in top form.

Among the best for: The South, Fixer-Uppers, College Towns, Waterfront, Retirees, City Living, Rowhouses, History Happened Here, Easy Commute, Walkability