Though I've written before that Laurel Park is the most charming neighborhood in Sarasota, over the last several years, Gillespie Park has really come into its own and may be giving Laurel a run for its money. A few decades ago, it wasn't the best of neighborhoods and most people didn't feel safe walking through it after dark. However, many of the original homes built in the 1920s have been restored, new homes have been built, yet affordable rental housing is still available, making Gillespie Park the most economically diverse and eclectic neighborhood in Downtown Sarasota, if not the entire county.
The neighborhood is named for John Gillespie, the Scottish immigrant who became Sarasota's first mayor and built the first golf course in the United States right here in Sarasota. Walking down the numbered streets and admiring the restored houses, you can't help but see a reverence for history. The new homes you pass, however, hint at the progress underlying the neighborhood's transformation. 7th Street was one of the first to embrace the idea of restoring the near-century old homes, and now the street is a promenade of award-winning landscaping and home renovation.
One of the most engaging restorations are the Boat and Lighthouse at the corner of Osprey and Fifth. The quirky structures were built in 1933 for Arthur Rowe, the yacht captain for John Ringling and William Selby. These days, these unique cottages provide a really great vacation spot through AirBnB, the perfect accommodations if you'd like to have fun exploring the neighborhood for a few days.
Another great way to immerse yourself in this eclectic neighborhood is by visiting the Historic Downtown Village just off Fruitville Road where a number of vintage cottages have been transformed into tea houses, spas, boutiques, restaurants, shops, and studios. Every First Friday, there is a special event featuring live music, extended hours, games for the kids, and special deals. Having the Historic Downtown Village as part of the neighborhood is an amazing perk of living in Gillespie Park, but an even greater perk is that Main Street and all the other downtown amenities are within a short walking distance.
The cornerstone of Gillespie Park, however, is the park itself. Developed by Owen Burns in 1924, today the park is one of the largest neighborhood recreational facilities in the county. Featuring tennis courts, a recently refurbished playground, and a meandering path through majestic oaks, the park offers plenty of opportunity for exercise and reflection. The Gallery of Patriots, featuring a variety of busts of North and South American leaders, celebrates the cultural diversity of the neighborhood, and the pond is home to a number of water fowl and turtles.
For dining, Gillespie Park is literally surrounded by some of Sarasota's best eateries. La Primavera serves up authentic Mexican food in the northeast corner, and on Tenth Street, which borders the neighborhood on the north, Maximillian's serves up arguably the best sandwiches and salads in town. To the west, Gillespie Park shares Orange Avenue with the quickly developing Rosemary District, where Citrus Square offers delectable dining at The Rosemary and Pomona restaurants, and the restored cottages to the south include The Breakfast House, which serves incredible omelets and more in a charming environment which includes outside dining.
Sarasota Area Real Estate Specialist