Introducing Gatsby Manor, set along Hillview Drive, one of Sarasotas most coveted bayfront addresses, often compared to Port Royal for its exclusivity and waterfront lifestyle, this rare Harbor Acres estate property spans nearly three quarters of an acre on deep, boatable water with sweeping, unobstructed Sarasota Bay views stretching south toward Siesta Key and the Gulf of Mexico, representing one of the neighborhoods most distinguished open bay offerings where only a select few residences achieve true estate scale. Encompassing more than 8,000 square feet of air conditioned space with four bedrooms and three and a half baths. The residence is complemented by a grand motor court accommodating 15+ vehicles beneath a canopy of majestic grand oaks. Privately approached through wrought iron gates and a sweeping circular drive anchored by a multi tiered fountain, the home opens to a dramatic two story foyer framing the water beyond. Interiors are defined by soaring ceilings up to 22 ft. in height, exceptional millwork, multiple fireplaces, a striking two story wood paneled library, formal dining with 12 foot ceilings, and a wetbarperfectly blending elegant entertaining with comfortable daily living. The chefs kitchen is designed to support both everyday living and large scale gatherings, featuring double 36 inch Sub Zero refrigerators with dual freezer drawers, two dishwashers, and a 60 inch Wolf gas range with six burners and infrared dual griddle. The owners suite occupies the entire east wing of the main living level, creating a private waterfront retreat complete with a gas fireplace, sitting area overlooking the pool and bay, dual walk in closets, and a spa inspired bath highlighted by a sculptural copper soaking tub, dual vanities, and a dedicated luxury makeup area. Upstairs, a second primary style suite and two additional guest bedrooms 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 homes ultimate entertaining environment, featuring a remarkable speakeasy lounge and an impressive 700+ bottle wine room. This expansive space functions as a true extension of the residences living experienceideal for hosting gatherings, intimate evenings, or celebrations on a grand scale. Outdoor living is equally exceptional, centered around an expansive marble terrace 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 lift and seawall replaced in 2017 further enhance the propertys 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 positioned just a short stroll to Southside Villages restaurants and boutiques, minutes from downtown Sarasotas celebrated arts and cultural district, and only 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 Sarasotas most prestigious waterfront neighborhoods.