3440 Gulfmead Drive, Sarasota, FL 34242
$13,950,000 - For Sale
Property Details
Price: $13,950,000
Sq Ft: 6,596
($2,115 per sqft)
Bedrooms: 5
Bathrooms: 4
Partial Baths: 2
City:Sarasota
County:Sarasota
Type:Single Family Reside
Development:Gulfmead Estates
Subdivision:Gulfmead Estates
Acres:0.72
Year Built:2008
Listing Number:A4679384
Status Code:A-Active
Taxes:$58.00
Tax Year: 2025
Garage: 6
Furnishings: Unfurnished
Pets Allowed: Yes
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Equipment:
Bar Fridge
Dishwasher
Disposal
Dryer
Electric Water Heater
Exhaust Fan
Ice Maker
Kitchen Reverse Osmosis System
Microwave
Range
Range Hood
Refrigerator
Washer
Water Filtration System
Water Softener
Wine Refrigerator
Interior Features:
Built-in Features
Ceiling Fans(s)
Crown Molding
Eat-in Kitchen
Elevator
High Ceilings
Open Floorplan
PrimaryBedroom Upstairs
Solid Wood Cabinets
Split Bedroom
Stone Counters
Thermostat
Vaulted Ceiling(s)
Walk-In Closet(s)
Wet Bar
Window Treatments
Exterior Features:
French Doors
Lighting
Outdoor Shower
Rain Gutters
View:
Water
Waterfront Description:
Gulf/Ocean
Financial Information:
Taxes: $58.00
Tax Year: 2025
Room Dimensions:
Laundry: Electric Dryer Hookup, In
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Discover a rare opportunity to enjoy pristine Gulf views, aquamarine waters, and a deep-water dock on the very North end of Siesta Key, just minutes to downtown Sarasota. One of Siesta Key’s most stunning and secluded waterfront sites — a residence offering a rare combination of historic significance, panoramic views of Big Pass, and exceptional structural integrity. Located approximately 200 feet south of civic leader Henry Higel’s early 20th-century Higelhurst Hotel, the pioneering developer’s beloved coastal breezes still beckon family and friends to enjoy swimming, water sports, boating, fishing, shoreline picnics, and direct, no-bridge access to the sparkling Gulf. Multiple covered porches and expansive windows provide front-row views of vivid sunsets and frolicking dolphins. Named for its pineapple stair finials symbolizing welcome, the Pineapple House was built in 2008 with an engineer-homeowner’s meticulous eye for detail. Constructed on pilings and grade beams, the home is set on a 31,293-square-foot lot and encompasses 6,596 square feet under air, with more than 13,000 total square feet. Designed by Diane Weinman with a refined Boca Grande aesthetic and built by ML Collingwood, the dwelling projects enduring quality, thoughtful engineering, and elevated coastal living. Enter through the impressive double doors to a sensual treat of symmetry and light. Main-level windows crowned with transoms frame views of the tropical blue sky. Walnut engineered flooring, Jerusalem stone, eight-foot doors, custom millwork, and generous closets enhance both functionality and beauty throughout. Scaled to feel both warm and elegant, the interiors are enriched with refined finishes and thoughtful architectural detailing. Living spaces encompass a formal dining room with butler’s pantry, living room, bookcase-lined library or sitting room, private office with built-in desk and cabinetry, dedicated home gym, and a flexible gathering room. A second primary or guest suite on the main level offers a private sitting area, breakfast bar, screened porch, and picture-perfect water views. An elevator conveniently serves all three floors. The chef’s kitchen anchors the main living areas with honed granite countertops, Sub-Zero appliances, custom Campbell cabinetry, and a walk-in pantry, opening to casual dining spaces and sun-filled outdoor porches. Upstairs, the primary suite is a tranquil retreat featuring a spa-inspired bath, oversized walk-in closet, shaded terrace, and outdoor shower. The expansive dock features two boat lifts: one 22,000-pound lift suitable for a 32- to 36-foot vessel and a second 10,000-pound lift. A humidity-controlled four-car tandem garage and a separate two-car garage accommodate up to six vehicles along with extensive marine and recreational gear. Solar panels and a 30kW generator underscore the home’s focus on energy efficiency and resilience. Outdoor living is highlighted by a 20,000-gallon heated saltwater lap pool surrounded by Shellcrete patios and Ipe decking. A perched beach with fire pit and swings welcomes gatherings overlooking Big Pass, while a 75-foot rear setback ensures privacy within a lushly landscaped yard. Rich in history, resilient and luxurious, intimate and refined, this is Sarasota waterfront living at its most authentic and coveted.
MLS Area: 34242 - Sarasota/Crescent Beach/Siesta Key
Price per Square Feet: $2,114.92
Total Floors: 3
Water: Public, Well
Lot Desc.: Floodzone, City Limits, Landscaped, Street Dead-End, Paved
Construction: Block, Concrete, Stucco
Date Listed: 2026-01-22 19:08:58
Pool: Yes
Pool Type: In Ground, Lap, Salt Water
Private Spa: No
Furnished: Unfurnished
Windows: Drapes, Rods, Storm Window(S)
Parking: Tandem, Workshop In Garage
Garage Spaces: 6
Flooring: Brick, Other, Wood
Roof: Metal
Heating: Central, Electric, Zoned
Cooling: Central Air, Zoned
Pets: Yes
Sewer: Public Sewer
Listing Courtesy Of: Michael Saunders & Company
JenniferLinehan@MichaelSaunders.com
Discover a rare opportunity to enjoy pristine Gulf views, aquamarine waters, and a deep-water dock on the very North end of Siesta Key, just minutes to downtown Sarasota. One of Siesta Key’s most stunning and secluded waterfront sites — a residence offering a rare combination of historic significance, panoramic views of Big Pass, and exceptional structural integrity. Located approximately 200 feet south of civic leader Henry Higel’s early 20th-century Higelhurst Hotel, the pioneering developer’s beloved coastal breezes still beckon family and friends to enjoy swimming, water sports, boating, fishing, shoreline picnics, and direct, no-bridge access to the sparkling Gulf. Multiple covered porches and expansive windows provide front-row views of vivid sunsets and frolicking dolphins. Named for its pineapple stair finials symbolizing welcome, the Pineapple House was built in 2008 with an engineer-homeowner’s meticulous eye for detail. Constructed on pilings and grade beams, the home is set on a 31,293-square-foot lot and encompasses 6,596 square feet under air, with more than 13,000 total square feet. Designed by Diane Weinman with a refined Boca Grande aesthetic and built by ML Collingwood, the dwelling projects enduring quality, thoughtful engineering, and elevated coastal living. Enter through the impressive double doors to a sensual treat of symmetry and light. Main-level windows crowned with transoms frame views of the tropical blue sky. Walnut engineered flooring, Jerusalem stone, eight-foot doors, custom millwork, and generous closets enhance both functionality and beauty throughout. Scaled to feel both warm and elegant, the interiors are enriched with refined finishes and thoughtful architectural detailing. Living spaces encompass a formal dining room with butler’s pantry, living room, bookcase-lined library or sitting room, private office with built-in desk and cabinetry, dedicated home gym, and a flexible gathering room. A second primary or guest suite on the main level offers a private sitting area, breakfast bar, screened porch, and picture-perfect water views. An elevator conveniently serves all three floors. The chef’s kitchen anchors the main living areas with honed granite countertops, Sub-Zero appliances, custom Campbell cabinetry, and a walk-in pantry, opening to casual dining spaces and sun-filled outdoor porches. Upstairs, the primary suite is a tranquil retreat featuring a spa-inspired bath, oversized walk-in closet, shaded terrace, and outdoor shower. The expansive dock features two boat lifts: one 22,000-pound lift suitable for a 32- to 36-foot vessel and a second 10,000-pound lift. A humidity-controlled four-car tandem garage and a separate two-car garage accommodate up to six vehicles along with extensive marine and recreational gear. Solar panels and a 30kW generator underscore the home’s focus on energy efficiency and resilience. Outdoor living is highlighted by a 20,000-gallon heated saltwater lap pool surrounded by Shellcrete patios and Ipe decking. A perched beach with fire pit and swings welcomes gatherings overlooking Big Pass, while a 75-foot rear setback ensures privacy within a lushly landscaped yard. Rich in history, resilient and luxurious, intimate and refined, this is Sarasota waterfront living at its most authentic and coveted.
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Additional Information:
MLS Area: 34242 - Sarasota/Crescent Beach/Siesta Key
Price per Square Feet: $2,114.92
Total Floors: 3
Water: Public, Well
Lot Desc.: Floodzone, City Limits, Landscaped, Street Dead-End, Paved
Construction: Block, Concrete, Stucco
Date Listed: 2026-01-22 19:08:58
Pool: Yes
Pool Type: In Ground, Lap, Salt Water
Private Spa: No
Furnished: Unfurnished
Windows: Drapes, Rods, Storm Window(S)
Parking: Tandem, Workshop In Garage
Garage Spaces: 6
Flooring: Brick, Other, Wood
Roof: Metal
Heating: Central, Electric, Zoned
Cooling: Central Air, Zoned
Pets: Yes
Sewer: Public Sewer
Map of 3440 Gulfmead Drive, Sarasota, FL 34242
Listing Courtesy Of: Michael Saunders & Company
JenniferLinehan@MichaelSaunders.com
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