1240 HILLVIEW DRIVE, SARASOTA, FL 34239

$16,950,000

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… Read More 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. Read Less

Courtesy of COLDWELL BANKER REALTY 941-383-6411

Listing Snapshot

Days Online

Last Updated

Apr 9, 2026

Property Type

Single Family Residence

Beds

Full Baths

Partial Baths

Square Ft.

4,852

Lot Size

0.73 Acres

Year Built

1992

MLS Number

A4688990

Additional Details

Property Access

Road Surface: Asphalt

Appliances & Equipment

Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Freezer, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator

Building

Built in 1992, Living area: 4852, Living area units: Square Feet, Building faces North, 3 stories, Levels: Three Or More, Construction Materials: Block, Stucco, Frame

Cooling

Central Air, Zoned

Exterior Features

Patio/Porch Features: Covered, Deck, Patio, Porch, Rear Porch, Balcony, Courtyard, French Doors, Lighting, Storage

Fence

Fenced

Fireplaces

Family Room, Living Room, Primary Bedroom, Wood Burning

Floors

Carpet, Marble, Wood

Foundation

Slab

Garage

3 spaces

Heating

Central, Electric, Natural Gas, Zoned

Interior Features

Cathedral Ceiling(s), Ceiling Fans(s), Central Vaccum, Crown Molding, Elevator, Kitchen/Family Room Combo, Open Floorplan, Solid Wood Cabinets, Split Bedroom, Stone Counters, Tray Ceiling(s), Vaulted Ceiling(s), Walk-In Closet(s)

Laundry

Inside, Laundry Room, Washer Hookup

Lot

0.73 acres, Dimensions: 309x101x345x100, Cleared, FloodZone, City Limits, Oversized Lot, Street Dead-End, Paved, Mature Landscaping, Oak Trees, Trees/Landscaped

Parking

Circular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Garage Faces Side, Ground Level, Open, Oversized

Pets Policy

Allowed: Yes

Pool

Heated, In Ground, Salt Water

Property

Completed, Other structures: Storage, Water

Roof

Concrete, Tile

Security Features

Security Fencing/Lighting/Alarms, Secured Garage/Parking, Security Gate, Security Lights, Security System Owned, Smoke Detector(s)

Sewer

Public Sewer

Taxes

Additional parcels description:, Parcel Number: 2037130006, Public Survey Range: 18, Public Survey Section: 30, Annual Amount: $80,000, Tax Book Number: 0004/0063, Legal Description: LOT 153 HARBOR ACRES SEC 2, Lot: 153, Year: 2025, Zoning: RSFE

Utilities

BB/HS Internet Available, Cable Available, Electricity Available, Natural Gas Available, Public, Sewer Available, Sprinkler Well, Water Available, Water Source: Public

Water Features

Bay/Harbor

Windows

Blinds, Rods

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