Original Gillespie Park is a character-rich pocket just north of downtown Sarasota, where early 20th-century bungalows mingle with thoughtful infill and shady oaks frame sidewalks. At its heart is the neighborhood’s namesake green, Gillespie Park, a destination for locals thanks to tennis and pickleball courts, a dog park, playgrounds, a fitness court, and a tranquil pond frequented by herons and turtles. Weekends often start with a stroll to the nearby Rosemary District or into Sarasota for coffee, galleries, and performance venues.
Cultural outings are minutes away. The reimagined waterfront at The Bay delivers sunset walks, kayak launches, and free community events. Big-stage performances shine at the Van Wezel Performing Arts Hall and the storied Sarasota Opera, while Saturday mornings brim with local flavors at the Sarasota Farmers Market. Bike-friendly streets and quick access to major corridors make commuting simple, and the neighborhood’s grid encourages impromptu meetups on porches and at the park.
Families appreciate access to Sarasota County Schools, with nearby options such as Booker High School and a variety of magnet and charter programs around Sarasota County. Housing spans renovated cottages, colorful mid-century homes, and modern townhomes, offering choices for first-time buyers and seasoned movers alike.
Whether you’re planning your first home search here or preparing to list, Agent Pronto can introduce you to a local real estate professional who knows Original Gillespie Park block by block and can guide your next move with confidence.
