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Introducing “Gatsby Manor,” set along Hillview Drive, one of Sarasota’s 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 neighborhood’s 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 wet bar—perfectly blending elegant entertaining with comfortable daily living. The chef’s 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 owner’s 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 home’s 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 residence’s living experience—ideal 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 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 positioned just a short stroll to Southside Village’s restaurants and boutiques, minutes from downtown Sarasota’s 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 Sarasota’s most prestigious waterfront neighborhoods.

4 Beds ⋅ 4 Baths ⋅ Harbor Acres SubDv. ⋅ 34239 Zip Code

Introducing “Gatsby Manor,” set along Hillview Drive, one of Sarasota’s 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 neighborhood’s 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 wet bar—perfectly blending elegant entertaining with comfortable daily living. The chef’s 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 owner’s 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 home’s 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 residence’s living experience—ideal 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 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 positioned just a short stroll to Southside Village’s restaurants and boutiques, minutes from downtown Sarasota’s 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 Sarasota’s most prestigious waterfront neighborhoods.

1240 Hillview Drive, Sarasota

$6,999,900

Virtually Staged. Welcome to this exceptional waterfront home in the highly sought-after Harbor Acres neighborhood. With more than 5,000 square feet of living space, this five-bedroom, five-full-and-two-half-bath residence combines classic Spanish/Mediterranean style with comfortable living and beautiful waterfront views. Located on a private waterfront basin with direct access to Sarasota Bay, the home offers spectacular sunsets and an ideal setting for enjoying the Florida lifestyle. The home features two primary suites, one on each level. The first-floor suite has private garage access and is well suited for guests, extended family, or multigenerational living. The additional bedrooms offer flexibility for offices, a fitness room, or other uses. The spacious interior includes a gourmet kitchen with granite and quartz countertops, wet bar, wine cooler, breakfast bar, and open access to the family room. Multiple electric fireplaces add warmth and character, and an interior elevator provides easy access between floors. Outdoor living is a major highlight. Covered lanais on both levels overlook the heated PebbleTec pool, spa, and waterfront. A covered outdoor dining area with summer sink and pool bath provides an ideal space for entertaining. Tropical landscaping adds privacy and creates a relaxing resort-style setting. Boating enthusiasts will appreciate the deep-water dock with boat lift and room for a large vessel, with convenient access to Sarasota Bay and the surrounding waterways. The home is move-in ready and has been meticulously maintained. Recent improvements include three new AC/HVAC systems (2024), two new gas water heaters, a variable-speed Jandy pool pump, new seawall cap, and a 22KW Generac generator, along with more than $50,000 in additional upgrades. Harbor Acres is conveniently located near Downtown Sarasota, Lido Key, and Siesta Key, as well as excellent restaurants, boutique shopping, hospitals, medical offices, banks, and everyday conveniences. A rare opportunity to own a spacious waterfront home with direct Sarasota Bay access, excellent boating amenities, a private pool and spa, and flexible living spaces in one of Sarasota's most desirable neighborhoods.

5 Beds ⋅ 7 Baths ⋅ Harbor Acres SubDv. ⋅ 34239 Zip Code

Virtually Staged. Welcome to this exceptional waterfront home in the highly sought-after Harbor Acres neighborhood. With more than 5,000 square feet of living space, this five-bedroom, five-full-and-two-half-bath residence combines classic Spanish/Mediterranean style with comfortable living and beautiful waterfront views. Located on a private waterfront basin with direct access to Sarasota Bay, the home offers spectacular sunsets and an ideal setting for enjoying the Florida lifestyle. The home features two primary suites, one on each level. The first-floor suite has private garage access and is well suited for guests, extended family, or multigenerational living. The additional bedrooms offer flexibility for offices, a fitness room, or other uses. The spacious interior includes a gourmet kitchen with granite and quartz countertops, wet bar, wine cooler, breakfast bar, and open access to the family room. Multiple electric fireplaces add warmth and character, and an interior elevator provides easy access between floors. Outdoor living is a major highlight. Covered lanais on both levels overlook the heated PebbleTec pool, spa, and waterfront. A covered outdoor dining area with summer sink and pool bath provides an ideal space for entertaining. Tropical landscaping adds privacy and creates a relaxing resort-style setting. Boating enthusiasts will appreciate the deep-water dock with boat lift and room for a large vessel, with convenient access to Sarasota Bay and the surrounding waterways. The home is move-in ready and has been meticulously maintained. Recent improvements include three new AC/HVAC systems (2024), two new gas water heaters, a variable-speed Jandy pool pump, new seawall cap, and a 22KW Generac generator, along with more than $50,000 in additional upgrades. Harbor Acres is conveniently located near Downtown Sarasota, Lido Key, and Siesta Key, as well as excellent restaurants, boutique shopping, hospitals, medical offices, banks, and everyday conveniences. A rare opportunity to own a spacious waterfront home with direct Sarasota Bay access, excellent boating amenities, a private pool and spa, and flexible living spaces in one of Sarasota's most desirable neighborhoods.

1444 Harbor Drive, Sarasota

$11,450,000

Under Construction. Best price under construction opportunity in Harbor Acres, a one-third-acre waterfront property on the widest part of the neighborhood's deep-water harbor on Sarasota Bay. The views are great and the home is located on a protected, sailboat water basin with no bridges to the Gulf of Mexico. Newer boat dock and boat lifts accommodate up to 15,000-pound boat plus two recreational water craft, making easy access to Sarasota's waterways and the gulf, AND the home was designed by one of the BEST architectural firms, MHK, and under construction by one of the BEST waterfront builders, Voigt Brothers. The floor plan is amazing and the home is available for purchase during the construction phase. 4 bedrooms all ensuite, 5 bathrooms, 2 half bathrooms, elevator, 3 car garage, elevated pool with large entertaining deck plus covered pool terrace area with outdoor kitchen. Harbor Acres is considered one of the best neighborhoods in Sarasota— and speaking of BEST, it has it all… location, waterfront, appreciation, neighbors. A true neighborhood community that is close to Downtown Sarasota and in-town amenities yet a half mile to Sarasota Memorial Hospital and Southside Village shops and restaurants. Call for floor plans or to walk the property.

4 Beds ⋅ 7 Baths ⋅ Harbor Acres SubDv. ⋅ 34239 Zip Code

Under Construction. Best price under construction opportunity in Harbor Acres, a one-third-acre waterfront property on the widest part of the neighborhood's deep-water harbor on Sarasota Bay. The views are great and the home is located on a protected, sailboat water basin with no bridges to the Gulf of Mexico. Newer boat dock and boat lifts accommodate up to 15,000-pound boat plus two recreational water craft, making easy access to Sarasota's waterways and the gulf, AND the home was designed by one of the BEST architectural firms, MHK, and under construction by one of the BEST waterfront builders, Voigt Brothers. The floor plan is amazing and the home is available for purchase during the construction phase. 4 bedrooms all ensuite, 5 bathrooms, 2 half bathrooms, elevator, 3 car garage, elevated pool with large entertaining deck plus covered pool terrace area with outdoor kitchen. Harbor Acres is considered one of the best neighborhoods in Sarasota— and speaking of BEST, it has it all… location, waterfront, appreciation, neighbors. A true neighborhood community that is close to Downtown Sarasota and in-town amenities yet a half mile to Sarasota Memorial Hospital and Southside Village shops and restaurants. Call for floor plans or to walk the property.

1340 Harbor Drive, Sarasota

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