McClellan Park traces back to 1916, when sisters Katherine and Daisietta McClellan pooled their resources to buy 56 acres at the southern end of Orange Avenue and build what they marketed as Sarasota’s Garden Spot. They hired landscape architects to curve the roadways over the gently sloping land so that nearly every lot caught a view of the bay, then added a clubhouse with tennis and croquet and dredged a private yacht basin for residents only.

Today, paved sidewalks connect McClellan Park to South Village’s shops, restaurants, and cafes, and the neighborhood’s proximity to Sarasota Memorial Hospital draws a lot of medical professionals. Vintage homes here still carry their Spanish and Mediterranean detailing even after updates, though a handful of eclectic originals have given way to newer custom builds as large as 9,000 square feet, many overlooking Sarasota Bay. Towering oaks, swaying palms, and ivy-covered retaining walls line the streets, and a pet-friendly hiking park adds an easy way to get exercise close to home.