USAFLSarasotaHarbor Acres1240 Hillview Dr
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$16,950,000

For Sale

13 days ago

1240 Hillview Dr, Sarasota, FL

House

MLS® A4688990

4 Bed

4 Bath

4852 sqft

3 Parking

  • Key Facts
  • Description
  • Rooms
  • Map

Key Facts

Type Single Family Residence
Levels Residential
Size 4852 sqft
Garage Yes
Taxes $80,000
Days Active 13
Lot Size 
Approx. Age 1992
Avg. Price Per Sqft $3,493
MLS® Number A4688990

Property Address: 1240 Hillview Dr, SARASOTA, FL, 34239-2020

Average square foot calculated using Size range provided by listing agent.

Description

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.
MLS® NumberA4688990
Laundry LevelEnsuite
Central VacNo
FireplaceNo
Acreage
Exterior
GarageYes
Approx. Age1992
Basement
DrivewayCircular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Garage Faces Side, Ground Level, Open, Oversized
Garage Spaces
Heat
A/C
Heating Fuel

Extras

Rooms

Change to metres

Bonus Room:First FloorNot available
Bedroom 4:Third Floor18 × 12 ft
Other:Second Floor19 × 20 ft
Dining Room:Second Floor16 × 14 ft
Other:Second Floor12 × 9 ft
Bedroom 2:Third Floor13 × 13 ft
Bedroom 3:Third Floor12 × 14 ft
Kitchen:Second Floor18 × 16 ft
Family Room:Second Floor25 × 17 ft
Other:Second FloorNot available
Office:Second Floor16 × 13 ft
Living Room:Second Floor26 × 23 ft

Price History

-End Date
Not Sold YetSold Price

For Sale

Apr 8, 2026List Date
$16,950,000List Price

Home Appraisal

This property is estimated to sell between: $2,254,000 and $24,298,000.
Similar properties in this area sold on average for: $2,254,100
Expected to sell in 52 days. Similar properties sold in 65 days. This home has been on eXp Realty for 13 days.

The estimated sale price does not take into account many variables such as recent renovations, type of appliances, school district etc. To get a more accurate estimate please contact agent.

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1240 Hillview Dr, Sarasota, FL

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