1240 HILLVIEW DRIVE

SARASOTA, FL 34239

Introducing “Gatsby Manor,” set along Hillview Drive, one of Sarasota’s most coveted bayfront addresses, often compared to Port Royal for itsexclusivity and waterfront lifestyle, this rare Harbor Acres estate property spans nearly three-quarters of an acre on deep, boatable water withsweeping, unobstructed Sarasota Bay views stretching south toward Siesta Key and the Gulf of Mexico, representing one of the neighborhood’smost distinguished open-bay offerings where only a select few residences achieve true estate scale. Encompassing more than 8,000 square feetof air-conditioned space with four bedrooms and three-and-a-half baths, the residence is complemented by a grand motor court accommodating15+ vehicles beneath a canopy of majestic grand oaks. Privately approached through wrought-iron gates and a sweeping circular drive anchoredby a multi-tiered fountain, the home opens to a dramatic two-story foyer framing the water beyond. Interiors are defined by soaring ceilings up to22 ft. in height, exceptional millwork, multiple fireplaces, a striking two-story wood-paneled library, formal dining with 12-foot ceilings, and a wetbar—perfectly blending elegant entertaining with comfortable daily living. The chef’s kitchen is designed to support both everyday living andlarge-scale gatherings, featuring double 36-inch Sub-Zero refrigerators with dual freezer drawers, two dishwashers, and a 60-inch Wolf gas rangewith six burners and infrared dual griddle. The owner’s suite occupies the entire east wing of the main living level, creating a private waterfrontretreat complete with a gas fireplace, sitting area overlooking the pool and bay, dual walk-in closets, and a spa-inspired bath highlighted by asculptural copper soaking tub, dual vanities, and a dedicated luxury makeup area. Upstairs, a second primary-style suite and two additional guestbedrooms are accessed via the grand staircase or three-stop elevator, offering privacy and flexibility for family and guests. The 3,800+ square-foot ground-level bonus area serves as the home’s ultimate entertaining environment, featuring a remarkable speakeasy lounge and animpressive 700+ bottle wine room. This expansive space functions as a true extension of the residence’s living experience—ideal for hostinggatherings, intimate evenings, or celebrations on a grand scale. Outdoor living is equally exceptional, centered around an expansive marbleterrace surrounding the 25’ × 60’ heated saltwater pool with integrated sun shelf and spa. A brand new deep-water dock with a 20,000 lb boat liftand seawall replaced in 2017 further enhance the property’s boating capabilities and long-term value. Additional highlights include hurricane-rated garage doors, elevator access to all three levels, a drive-through three-car garage, and extensive storage throughout. Perfectly positionedjust a short stroll to Southside Village’s restaurants and boutiques, minutes from downtown Sarasota’s celebrated arts and cultural district, andonly four blocks from Sarasota Memorial Hospital, Gatsby Manor offers a truly rare opportunity to enjoy estate-scale open-bay living with deep water, privacy, and exceptional walkability in one of Sarasota’s most prestigious waterfront neighborhoods.

Listing courtesy of COLDWELL BANKER REALTY (305) 205-7700



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Last checked: 2026-04-08 09:22 AM EDT