With the Sarasota housing market continuing its strong momentum into 2025, savvy homebuyers are looking beyond simple profit potential. They’re seeking neighborhoods that offer character, walkability, and a true sense of place. One such standout is Gillespie Park Sarasota, a historic enclave just north of Downtown.

📍 Where is Gillespie Park Sarasota?

Nestled north of Fruitville Road and bordered by Orange Avenue and Washington Boulevard, Gillespie Park boasts a rich history that dates back to the early 1900s. The neighborhood is named after Sarasota’s first mayor, John Gillespie, and many of the homes built in the 1920s have been lovingly restored. Some are even eligible for inclusion in the National Register of Historic Places.

🏡 Architecture with Authenticity

Walking through Gillespie Park feels like a tour through Florida’s architectural past and present. You’ll find a diverse mix of styles—Mediterranean, Spanish Colonial, Florida ranch, and even homes with Caribbean influences. This eclectic blend gives the neighborhood its unique charm and wide appeal among buyers seeking homes with personality.

💰 Gillespie Park Real Estate Market (2025 Update)

The real estate market in Gillespie Park continues to surge, reflecting Sarasota’s overall growth. As of early 2025:

• Median Listing Price: $987,300 (up 16.2% YoY)
• Median Sale Price: $683,000 (up 4.3% YoY)
• Price per Square Foot: $450–$530

A few years ago, a remodeled 3-bedroom, 2-bathroom ranch-style home on a large lot could be found for under $500,000. Today, similar properties start around $724,900—and they don’t stay on the market long. Latest pricing at Gillespie Park Sarasota Florida will be found below if there is inventory.

🧩 Mixed-Use Zoning & Creative Possibilities

Gillespie Park stands out not only for its curb appeal but also for its zoning flexibility. Homeowners can operate select businesses—think cafés, boutiques, art studios, and professional offices—from their properties. This makes it an ideal location for entrepreneurs, creatives, and remote workers.

On top of that, many homes sit on generously sized lots, offering the potential to build detached dwellings or rental units. A recent listing, for example, featured three charming bungalows on a single property with room to add a fourth—all for around $649,000. It’s a dream setup for anyone looking to live, work, and invest in one of Sarasota’s most promising neighborhoods.

🌳 Community Vibes & Green Spaces

Gillespie Park isn’t just about real estate—it’s about lifestyle. Towering oak trees, shaded sidewalks, and a strong sense of community pride define the neighborhood. In the heart of the community lies the Gillespie Park Recreation Area, complete with:

• A playground
• Tennis courts
• A pond
• A covered pavilion perfect for gatherings

Residents often organize block parties and neighborhood events, creating a welcoming environment for families, single professionals, and retirees alike.

🏁 Final Thoughts

Whether you’re searching for a primary residence, a rental property, or a hybrid live-work setup, Gillespie Park Sarasota offers an unbeatable blend of historic charm, investment potential, and modern convenience. Just minutes from downtown Sarasota and rich with character, it’s no surprise that this neighborhood continues to attract interest from buyers across the country.

If you’re looking to put down roots in a place where tradition meets opportunity, Gillespie Park Sarasota should be at the top of your list.

Gillespie Park Sarasota Florida Homes for Sale

See all Gillespie Park Sarasota Homes for Sale.
(all data current as of 9/27/2025)

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