1240 Hillview Drive, Sarasota, FL 34239
Local realty services provided by:CENTURY 21 Selling Paradise
1240 Hillview Drive,Sarasota, FL 34239
$16,950,000
- 4 Beds
- 4 Baths
- 4,852 sq. ft.
- Single family
- Active
Listed by: ryan ackerman, pa, barbara ackerman
Office: coldwell banker realty
MLS#:A4688990
Source:MFRMLS
Price summary
- Price:$16,950,000
- Price per sq. ft.:$1,928.33
About this home

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 wetbar—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....
Contact an agent
Home facts
- Year built:1992
- Listing ID #:A4688990
- Added:1 day(s) ago
- Updated:April 09, 2026 at 04:23 AM
Rooms and interior
- Bedrooms:4
- Total bathrooms:4
- Full bathrooms:3
- Half bathrooms:1
- Flooring:Carpet, Marble, Wood
- Dining Description:Breakfast Room, Formal Dining Room
- Kitchen Description:Bar Fridge, Built-In Oven, Dishwasher, Disposal, Freezer, Kitchen/Family Room Combo, Range, Range Hood, Refrigerator, Solid Wood Cabinets, Stone Counters, Wine Refrigerator
- Bedroom Description:Split Bedroom, Walk-In Closet(s)
- Living area:4,852 sq. ft.
Heating and cooling
- Cooling:Central Air, Zoned
- Heating:Central, Electric, Natural Gas, Zoned
- Central air:Yes
Structure and exterior
- Roof:Concrete, Tile
- Year built:1992
- Building area:4,852 sq. ft.
- Lot area:0.73 Acres
- Lot Features:Cleared, Flood Zone, Oversized, Paved
- Architectural Style:Custom
- Construction Materials:Block, Frame, Stucco
- Exterior Features:Balcony, Courtyard, Covered Porch/Patio, Deck, Lighting, Patio, Porch, Rear Porch
- Foundation Description:Slab
- Levels:Three Or More Story
Schools
- High school:Sarasota High
- Middle school:Sarasota Middle
- Elementary school:Southside Elementary
Utilities
- Water:Public, Water Available
- Sewer:Public, Public Sewer, Sewer Available
Finances and disclosures
- Price:$16,950,000
- Price per sq. ft.:$1,928.33
- Tax amount:$80,000 (2025)
Features and amenities
- Appliances:Bar Fridge, Built-in Oven, Dishwasher, Disposal, Dryer, Freezer, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
- Laundry features:Dryer, Inside, Laundry Room, Washer, Washer Hookup
- Amenities:BB/HS Internet Available, Cable Available, Cathedral Ceiling(s), Ceiling Fans(s), Central Vaccum, Crown Molding, Electricity Available, Elevator, Kitchen/Family Room Combo, Natural Gas Available, Open Floorplan, Solid Wood Cabinets, Split Bedroom, Sprinkler Well, Stone Counters, Tray Ceiling(s), Vaulted Ceiling(s), Walk-In Closet(s)
- Pool features:Heated, In Ground, Private Pool, Salt Water
Parking
- Parking description:Attached Garage, Circular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Garage Faces Side, Ground Level, Open, Oversized
- Garage:Yes
- Garage spaces:3
New listings near 1240 Hillview Drive
- Open Sun, 1am to 4pmNew
$2,450,000Active2 beds 2 baths1,940 sq. ft.6140 Midnight Pass Road #904, SARASOTA, FL 34242
MLS# A4682903Listed by: COLDWELL BANKER REALTY - New
$7,900,000Active3 beds 4 baths5,600 sq. ft.128 Golden Gate Point #901B, SARASOTA, FL 34236
MLS# A4687889Listed by: COLDWELL BANKER REALTY - New
$415,000Active3 beds 2 baths1,686 sq. ft.4341 Nelson Avenue, SARASOTA, FL 34231
MLS# A4688886Listed by: COLDWELL BANKER REALTY - New
$179,000Active2 beds 2 baths1,206 sq. ft.4160 Fruitville Road #11, SARASOTA, FL 34232
MLS# A4689204Listed by: BLUE SKY REAL ESTATE - New
$799,999Active3 beds 3 baths1,831 sq. ft.5351 Moeller Avenue, SARASOTA, FL 34233
MLS# A4689390Listed by: DALTON WADE INC - New
$629,000Active2 beds 2 baths1,541 sq. ft.2753 Valencia Drive, SARASOTA, FL 34239
MLS# TB8493972Listed by: COASTAL PROPERTIES GROUP INTERNATIONAL - New
$1,049,999Active1 beds 1 baths782 sq. ft.711 Beach Road #408, SARASOTA, FL 34242
MLS# A4689303Listed by: HARRY ROBBINS ASSOC INC - New
$810,000Active3 beds 3 baths2,656 sq. ft.4801 Edgemont Court, SARASOTA, FL 34233
MLS# A4687407Listed by: JOHN HARDING REALTY - New
$2,895,000Active3 beds 5 baths5,742 sq. ft.3129 Founders Club Drive, SARASOTA, FL 34240
MLS# A4689202Listed by: PREMIER SOTHEBY'S INTERNATIONAL REALTY - New
$179,000Active2 beds 2 baths800 sq. ft.5308 Tri Par Drive, SARASOTA, FL 34234
MLS# A4689063Listed by: EXIT KING REALTY