Historic Gillespie Park Home | Luxury Downtown Sarasota Living on Three Lots! Discover a rare opportunity to own a beautifully restored historic home in Gillespie Park, one of Downtown Sarasota's most desirable historic neighborhoods. Originally built during Florida's celebrated Land Boom of the 1920s, this exceptional residence has been thoughtfully expanded and extensively renovated, preserving its timeless architectural character while seamlessly incorporating the modern amenities today's luxury buyers expect. Occupying 3 lots, this remarkable property offers an extraordinary combination of privacy, mature landscaping, and expansive outdoor living spaces just moments from Downtown Sarasota, The Bay Park, the Rosemary District, Sarasota Bay, Marina Jack, boutique shopping, acclaimed restaurants, theaters, galleries, and the city's vibrant cultural scene. Whether you're searching for a luxury primary residence or a distinctive historic Sarasota home, this property delivers an unmatched downtown lifestyle. A substantial two-story addition completed in 2019 expanded the home by approximately 800 square feet, creating a floor plan designed for modern living while remaining true to the home's original architecture. The addition enlarged the chef's kitchen and added a full bathroom, pantry, utility room, and reading room on the main level. Upstairs, the primary suite was transformed into a luxurious retreat with a spa-inspired bathroom and dual walk-in closets. At the heart of the home is a beautifully renovated chef's kitchen featuring premium Thermador appliances, including three ovens, a six-burner gas cooktop, custom cabinetry, granite countertops, and a charming bay window overlooking the professionally landscaped gardens. Rich hardwood flooring, renovated bathrooms, fresh interior paint, generous bedrooms, and preserved architectural details create the perfect balance between historic elegance and contemporary comfort. Extensively updated for comfort, efficiency, and peace of mind, the residence features custom hurricane-impact windows installed in 2024 and designed to replicate the home's original windows while providing modern storm protection, energy efficiency, and enhanced sound insulation. Additional improvements include a new roof (2022), an expansive screened lanai completed in 2022 and enhanced with an upgraded drainage system in 2025, a new driveway, gutters, underground drainage, professionally installed irrigation, and two air-conditioning systems. Professionally designed Florida-native landscaping, winding brick pathways, tranquil gardens, and a newly established butterfly garden create a peaceful retreat rarely found this close to the heart of Sarasota. Offering the rare combination of a fully renovated historic Sarasota home, three separately platted lots, luxury finishes, modern infrastructure, and an exceptional Downtown Sarasota location, this one-of-a-kind residence is ideally positioned near The Bay Park, Sarasota Bay, the Rosemary District, Marina Jack, the Sarasota Farmers Market, Selby Botanical Gardens, the Sarasota Opera House, boutique shopping, award-winning dining, and the area's world-renowned Gulf beaches. Rich in history yet thoughtfully designed for today's lifestyle, this extraordinary home presents a rare opportunity to experience the very best of Downtown Sarasota luxury living.