Gillespie Park was originally planned as an experimental farm to champion agriculture in 1886 for the then-new city of Sarasota, but when its soil proved inhospitable to crops, it was platted as a city subdivision in 1917. Today, this recently rejuvenated community—one of three historic downtown neighborhoods undergoing city-sponsored revitalization efforts brought about by New Urbanist Andres Duany—is a charming collection of colorfully restored cottages and bungalows built in the 1920s, ’30s and ’40s as well as a few midcentury ranch houses. Residents are quick to insist that Gillespie Park, named for the first mayor of Sarasota, John Gillespie, is the “antisuburb” thanks in large part to its proximity to downtown Sarasota. Just a few blocks from the bay, this front-porch community marries a traditional neighborhood setting, where friendly neighbors share daily anecdotes and a bottle of wine in their front yards and high-school marching bands practice in the street, with a hip urban core, where a screening during the annual Sarasota Film Festival is just around the corner.

With approximately 500 residences, Gillespie Park is home to young professionals as well as empty nesters, plus the celebrated Honeygo Park, a 10-acre green space where locals gather for neighbor- hood brunches, outdoor concerts and afternoon strolls. Like many historic communities, there’s definitely no shortage of cute here. Residents congregate at the Breakfast House, a neighborhood café in a little yellow cottage that’s renowned for pineapple pancakes. “It’s not for everyone,” says Valarie Wadsworth, real-estate agent and vice president of the Original Gillespie Park Neighborhood Association. “It’s about the lifestyle and community, not the 4,000-square-foot house.” (Most homes in the area range from 800 to 1,000 square feet.) With front porches on nearly every home and no attached garages, Wadsworth continues, “You really know everyone who lives here because of the way the houses are built, and that brings a neighborhood together.”