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Gillespie Park

This area, located just north of downtown Sarasota, is densely packed with historic homes from the 1920s and 1930s, many of which have recently been refurbished. Gillespie Park is a fantastic place to live or invest right now. Poets, too, must retire, and Gillespie Park is the ideal location. It’s close to downtown, yet it’s a world away. Although more and more infill homes are being created, the drawcard here is quirky ancient cottages. Gillespie Park is almost 50% gentrified, so if you value diversity in your life, this could be the spot for you. Many people are working-class, and there is still a lot of shoddy rental housing. However, enough college professors, ceramicists, yoga instructors, and playwrights have relocated to give the area a distinctly creative edge. Although property prices have been gradually growing for years, this up-and-coming community provides walkability, open spaces, and comparatively modest housing values. Gillespie Park, one of the county’s largest parks, is at the heart of the neighborhood. The park is named for John Gillespie, Sarasota’s first mayor and the designer of Florida’s first golf course, and has tennis courts, playgrounds, and a large pond. Gillespie Park has come into its own now that downtown and the Rosemary District are growing. The sleazy folks that used to hang around in the park have vanished, or at least most of them have, and the infamous mansion on Tenth Street that formerly belonged to Sarasota’s most renowned drug dealer has been gussied up and would look perfectly at home in Key West has been restored. Driving—or rather, walking—around Gillespie Park today, it’s clear that the park has turned a corner. Almost all of the cottages have been purchased and restored. Even basic old concrete duplexes are being transformed into intriguing structures. The main news, though, is all of the new development. The majority of the houses are two-story and built in a modernist style that blends in with the neighborhood, with fascinating stone and ironwork accents. Many have a garage with an apartment above it at the back. They begin at roughly half a million dollars. A cottage that has been tastefully refurbished will cost a bit less. Gillespie Park turns the concept of a walkable neighborhood on its head. Instead of business activity in the center, it is concentrated on the outskirts. Downtown sits on the southern side, with all of its facilities directly across the street. The chic new Rosemary District lies on the western boundary, and you can sense the energy of the two new popular districts feeding off each other. On the eastern end, North Washington Boulevard, you’ll find a Popeye’s, a Mexican grocery shop, and a Buddhist Temple, among other things. People are already lining up to stroll to the 10-acre park, which has tennis courts, a lake, ducks to feed, and monuments of revolutionary heroes such as Simon Bolivar. There’s also a dog park and an exercise trail. The main allure of the area, though, is found in the residences themselves. On Seventh Street between Goodrich and Orange avenues, there’s a block of vividly colored cottages that’s truly reviving the area.

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