Gillespie Park

Gillespie Park sits just north of downtown Sarasota, built around the green space that gives the neighborhood its name and its rhythm — a walkable pocket where century-old bungalows share blocks with new construction. It's close enough to the Rosemary District and the arts-and-dining core that you can leave the car home, and near enough to the water that Lido Key beach days feel like an easy afternoon. The character here leans urban and eclectic — the kind of place where you know your neighbors and can still walk to a gallery opening.

For buyers, the market is doing two things at once. There are 15 active listings with a median list price of $1,650,000, but the range runs from $425,000 all the way to $2,995,000 — so what you pay depends heavily on whether you're buying an original cottage or one of the 7 new-construction homes now on the market. Over the last 12 months 12 homes sold at a median of $755,000, a real gap from list prices that tells you the higher-end new builds are still finding their buyers. If you want the same energy at a different price point, nearby Arlington Park is worth a look.

Gillespie Park is a community in Sarasota, Florida.