Gillespie Park in Sarasota : Homes for Sale in Every Architectural Style

With the Sarasota housing market firing on all cylinders in 2017, some home buyers are looking for real estate opportunities that offer more than just potential profit. If you are looking for homes that offer character as well as value, your best bet is to consider Gillespie Park in Sarasota.

Gillespie Park is located to the north of Fruitville Road, between Orange Avenue and Washington Boulevard. The neighborhood dates back to the early 1900s; in fact, some of the Old Florida homes in Gillespie Park were built in the 1920s and have been carefully renovated and preserved to conditions worthy of placement in the National Register of Historic Places.

Every architectural style in Southwest Florida can be found in this community, from Mediterranean to Spanish Colonial and from Florida ranch to Caribbean. Home values in Gillespie Park have greatly appreciated over the last few years thanks to the ongoing development of Downtown Sarasota. A remodeled Florida ranch home with three bedrooms and two bathrooms built on an oversize lot can be negotiated under $500K, but such listings tend to sell very fast.

Gillespie Park enjoys a special zoning situation that allows homeowners to operate certain businesses such as cafes, boutiques, art galleries, and professional offices within their properties. There are also opportunities to build detached structures in large lots; for example, a $649K listing in June 2017 consisted of three tastefully decorated bungalows with enough acreage to build another one, which means that a smart buyer could become a property investor as well as a landlord in a very lucrative rental market.

Mature oaks and sidewalks covered by leafy canopies can be found across the community. Residents know that this is an up-and-coming neighborhood in terms of property values; to this effect, the homes and gardens of Gillespie Park are meticulously kept. A public park in the middle of the neighborhood offers a playground, tennis courts, a pavilion, and even a pond.

Gillespie Park is perfect for families, single professionals and retirees. There is a strong sense of community pride that translates into block parties and neighborhood events. If you are looking for a traditional Sarasota lifestyle and a great investment opportunity, be sure to keep this neighborhood in mind.

Homes for Sale at Gillespie Park in Sarasota

See all Gillespie Park Sarasota Homes for Sale.
(all data current as of 1/31/2025)

Listing information deemed reliable but not guaranteed. Read full disclaimer.