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Gillespie Park is a historic, walkable neighborhood just north of downtown Sarasota, built around a 10-acre city park. We're Eric and Traci Bolen of Sand + Sea Homes with eXp Realty, a husband-and-wife team, and we'd love to help you buy or sell here.
History. Named for John Hamilton Gillespie, Sarasota's first mayor. Platted for homes after 1900; developer Owen Burns sold the city the 10-acre park parcel in 1924.
Homes. Bungalows, cottages and Mediterranean-style homes, many from the 1920s to 1940s, plus newer two-story construction.
The park. Tennis courts, picnic pavilion, playground, pond, dog park and the Gallery of Patriots busts.
Market
Price Range
Source: Stellar MLS, 12 months ending Oct 2026. Graphic by Sand + Sea Homes.
Stellar MLS shows 4 closed sales in Gillespie Park in the 12 months ending October 2026, with a median sale price of $852,500, a median of $419 per square foot and a median of 66 days on market. There was 1 active listing as of Oct. 21, 2026. Ask us for recent sales of homes with a similar plan, size and location.
Many downtown-area neighborhoods have voluntary associations rather than HOAs, while condos have their own associations, so we check these details with you line by line:
Tax bill and assessments. Ask for the latest property tax bill and check for CDD, stewardship district or other special assessments. Florida taxes also reset after a sale.
Association documents. Review the HOA budget, reserves, what the dues cover, and the leasing, pet and architectural rules before your inspection period ends. Condos and some neighborhoods have an extra association.
Insurance and flood zone. Get insurance quotes, and flood quotes where needed, before you're under contract. Flood zones are assigned home by home. Our post on whether Florida home insurance rates are coming down explains the current picture.
Zoned public schools for Gillespie Park, from Sarasota County Schools' School Zone Locator (checked Oct 20, 2026 using addresses inside the neighborhood):
Elementary and middle (K-8): Alta Vista School (K-8)
High: Booker High School
Sarasota County choice options include Pine View School in Osprey, the district's gifted magnet for grades 2-12 (eligibility testing required), and Booker Middle School's audition-based Visual and Performing Arts magnet. School boundaries change, so always confirm the assigned schools for a specific address with Sarasota County Schools before you buy.
Gillespie Park is one of the neighborhoods on our Downtown Sarasota list. Head back to our Downtown Sarasota homes and living guide for the big picture, or explore more of Downtown Sarasota:
Tennis courts, a pavilion, playground, pond and dog park on about 10 acres.
Which schools are zoned for Gillespie Park?
Based on Sarasota County Schools' School Zone Locator (checked Oct 20, 2026), Gillespie Park is zoned for Alta Vista School (K-8) and Booker High School. Boundaries change, so confirm the schools for a specific address with Sarasota County Schools.
