Gillespie Park Sarasota : Historic Downtown Homes for Sale

One of the most attractive subdivisions near Downtown Sarasota is also one of the most historic. Gillespie Park Sarasota is named after the first Mayor of Sarasota, a Scottish man who knew in the early 1900s that the downtown district was destined to become the jewel of Southwest Florida.

Ever since the large public park at the center of this neighborhood was completed in 1924, Gillespie Park has been one of Sarasota’s most endearing suburbs. The convenience of being located just blocks away from all the downtown museums, art galleries and performance centers, tends to attract young families and artists. This is a neighborhood with an Old Florida ambiance; many homes are built in the Florida ranch and Spanish Colonial styles, however, quite a few properties have been remodeled over the years.

Pricing in Gillespie Park Sarasota has always been considered to be very reasonable, especially when taking into account its proximity to Downtown Sarasota. In late 2024, the price of a historic, two-bedroom country home with a porch built in 1926 sold for $350K while two-bedroom townhouses with three-bathrooms built in the Modern architectural style were listed at $560K. Latest pricing at Gillespie Park Sarasota will be found below if there is inventory.

Some of the homes located closer to Fruitville Road enjoy mixed zoning privileges that allow owners to operate businesses from their properties; in recent years, this has resulted in the opening of neighborhood cafés and art galleries. Gillespie Park is next to Sarasota’s restaurant district and to Fruitville Road, where residents can find everything they need in terms of household goods. This is a very pedestrian neighborhood; many children can walk or ride their bikes to school, and the same goes for many residents who live just blocks away from shops and attractions.

The eponymous park at the center of this subdivision features nature trails, a pond, tennis courts, a pavilion, and a picnic area. Driving to the beaches of Siesta Key takes about 15 minutes.

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(all data current as of 6/17/2025)

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