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$13,950,000
New Listing

3440 GULFMEAD DRIVE
SARASOTA, FL 34242

For Sale|Single Family Residence|Active
5
Beds
6
Total Baths
4
Full Baths
2
Partial Baths
6,596
SqFt
$2,115
/SqFt
2008
Built
Subdivision:
GULFMEAD ESTATES
County:
Sarasota

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3440 GULFMEAD DRIVE3440 GULFMEAD DRIVE3440 GULFMEAD DRIVE3440 GULFMEAD DRIVE
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Monthly Payment (Est.)

$63,646
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2026 Information is deemed reliable but not guaranteed.

.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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Listing Snapshot
Price 
$13,950,000
Days On Site 
0 Days
Bedrooms 
5
Inside Area (SqFt) 
6,596 sqft
Total Baths 
6
Full Baths 
4
Partial Baths 
2
Lot Size 
0.72 Acres
Year Built 
2008
MLS® Number 
A4679384
Status 
Active
Property Tax 
$58,420.53
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
Public Records
Friends & Family
Recent Activity
6 hours agoListing updated with changes from the MLS®
6 hours agoListing first seen on site
General Features
Acres 
0.72
Attached Garage 
Yes
Direction Faces 
East
Energy Features 
Solar
Garage 
Yes
Garage Spaces 
6
Green Energy Efficient 
InsulationWater HeaterWindows
Levels 
One
Number Of Stories 
3
Parking 
TandemWorkshop in GarageAttached
Pets 
Yes
Property Sub Type 
Single Family Residence
Security 
Closed Circuit Camera(s)Fire AlarmSecurity SystemSecurity System OwnedSmoke Detector(s)
Sewer 
Public Sewer
SqFt Total 
13170
Style 
CustomFlorida
Utilities 
Cable AvailableCable ConnectedElectricity ConnectedNatural Gas AvailablePropaneSewer ConnectedWater Connected
Water Source 
PrivatePublicWell
Zoning 
RSF1
Interior Features
Appliances 
Bar FridgeDishwasherDisposalDryerElectric Water HeaterExhaust FanIce MakerMicrowaveRangeRange HoodRefrigeratorWasherWater SoftenerWine Refrigerator
Cooling 
Central AirZoned
Fireplace 
Yes
Fireplace Features 
Living RoomWood Burning
Flooring 
BrickOtherWood
Furnished 
Unfurnished
Heating 
CentralElectricZoned
Interior 
Built-in FeaturesCrown MoldingEat-in KitchenElevatorHigh CeilingsOpen FloorplanStone CountersVaulted Ceiling(s)Walk-In Closet(s)Wet Bar
Laundry Features 
Electric Dryer HookupInsideLaundry RoomWasher Hookup
Window Features 
DrapesStorm Window(s)
Bedroom 2 
Dimensions - 21x14Level - First
Bedroom 3 
Dimensions - 16x14Level - Second
Bedroom 4 
Dimensions - 11x20Level - Second
Bedroom 5 
Dimensions - 13x18Level - Second
Dinette 
Dimensions - 21x16Level - First
Dining Room 
Dimensions - 17x14Level - First
Kitchen 
Dimensions - 20x18Level - FirstFeatures - Breakfast Bar, Kitchen Island
Library 
Dimensions - 17x13Level - First
Living Room 
Dimensions - 17x29Level - First
Master Bedroom 
Dimensions - 18x17Level - SecondFeatures - Double Vanity
Office 
Dimensions - 14x14Level - First
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Exterior Features
Construction Details 
BlockConcreteStucco
Exterior 
LightingOutdoor ShowerRain GuttersDock
Fencing 
Fenced
Lot Features 
LandscapedPavedWaterfront
Patio And Porch 
CoveredEnclosedRear PorchScreenedSide PorchWrap Around
Pool Features 
In GroundLapSalt WaterPrivate
Private Pool 
Yes
Roof 
Metal
View 
Water
Waterfront 
Yes
Waterfront Features 
Ocean Front
Waterview 
Water
Windows/Doors 
DrapesStorm Window(s)
Community Features
Community Features 
Street Lights
Financing Terms Available 
CashConventional
MLS Area 
34242 - Sarasota/Crescent Beach/Siesta Key
Roads 
AsphaltPaved
Township 
36S
Listing courtesy of MICHAEL SAUNDERS & COMPANY (941) 266-7555



Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS.
Last checked: 2026-02-05 06:18 PM EST

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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