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3440 Gulfmead Drive

Sarasota, FL 34242
  • $13,950,000
  • STATUS: Active
  • ON SITE: 65 Days
  • MLS #: A4679384
UPDATED: 41 min ago
$13,950,000
  • 5
    BEDS
  • 0.72
    ACRES
  • 4
    BATHS
  • 2
    1/2 BATHS
  • 6,596
    SQFT
  • $2,115
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
2008
County:

School Ratings & Info

Description

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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© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-04-12T21:44:01.643.
www.realestatecentralfl.com/homes/172771993
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3440 Gulfmead Drive Sarasota, FL 34242

  • Price: $13,950,000
  • Status: Active
  • On Site: 65 Days
  • Updated: 41 min ago
  • MLS #: A4679384
5
Beds
4
Baths
2
½ Baths
0.72
Acres
6,596
SQFT
$2,115
$/SQFT
2008
Built
Neighborhood:
Gulfmead Estates
County:
Sarasota
Area:
Sarasota/Crescent Beach/Siesta Key
Property Description
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.
Exterior Features

Architectural Style CustomFlorida Attached Garage Yn Yes Carport Yn No Construction Materials BlockConcreteStucco Covered Spaces 6 Direction Faces East Exterior Features French DoorsIrrigation SystemLightingOutdoor ShowerRain Gutters Fencing Fenced Foundation Details Stilt/On Piling Garage Dimensions 26x41 Lot Features FloodZoneCity LotLandscapedStreet Dead-End Lot Size Dimensions 100 x 298 Parking Features TandemWorkshop in Garage Patio And Porch Features CoveredEnclosedRear PorchScreenedSide PorchWrap Around Pool Features In GroundLapSalt Water Pool Private Yn Yes Road Frontage Type Street Dead-EndStreet Paved Road Surface Type PavedAsphalt Roof Metal Spa YN No View Water Water Access Gulf/Ocean to Bay Water Access Yn Yes Water Body Name BIG PASS Water Extras LiftRiprapSailboat WaterSeawall - Concrete Water Extras Yn Yes Water View Gulf/Ocean - Full Water View Yn Yes Waterfront Features Gulf/Ocean Waterfront Feet Total 100 Waterfront Yn Yes

Interior Features

Additional Rooms AtticBreakfast Room SeparateDen/Library/OfficeFamily RoomFormal Dining Room SeparateFormal Living Room SeparateInside UtilityInterior In-Law Suite w/Private EntryStorage Rooms Appliances Bar FridgeDishwasherDisposalDryerElectric Water HeaterExhaust FanIce MakerKitchen Reverse Osmosis SystemMicrowaveRangeRange HoodRefrigeratorWasherWater Filtration SystemWater SoftenerWine Refrigerator Building Area Total 13170 Cooling Central AirZoned Cooling YN Yes Fireplace Features Living RoomWood Burning Fireplace Yn Yes Flooring Brick/StoneOtherHardwood Furnished Unfurnished Heating CentralElectricZoned Heating YN Yes Interior Features Built-in FeaturesCeiling Fan(s)Crown MoldingEating Space In KitchenElevatorHigh CeilingsOpen FloorplanPrimaryBedroom UpstairsSolid Wood CabinetsSplit BedroomStone CountersThermostatVaulted Ceiling(s)Walk-In Closet(s)Wet BarWindow Treatments Laundry Features Electric Dryer HookupInsideLaundry RoomWasher Hookup Levels One Sewer Public Sewer Stories Total 3 Water Source PublicWell Window Features DrapesRodsStorm Window(s)

Property Features

Additional Lease Restrictions See City of Sarasota guidelines Association Approval Required Yn No Association Yn No Builder Name ML Collingwood Cdd Yn No Down Payment Resource No Electric Photovoltaics Seller Owned Flood Zone Code AE Garage Yn Yes Green Energy Efficient InsulationWater HeaterWindows Green Energy Generation Solar Homestead Yn Yes Lease Considered YN Yes Lease Restrictions YN Yes Listing Terms CashConventional Minimum Lease 1 Week New Construction Yn No Number Of Wells 1 Ownership Fee Simple Pets Allowed Yes Property Condition Completed Property Sub Type Single Family Residence Realtor Info Brochure AvailableFloor Plan AvailableSign Security Features Closed Circuit Camera(s)Fire AlarmSecurity SystemSecurity System OwnedSmoke Detector(s) Senior Community Yn No Special Listing Conditions None Sw Subdiv Community Name Gulfmead Estates Tax Annual Amount 58420.53 Total Annual Fees 0 Total Monthly Fees 0 Utilities BB/HS Internet AvailableCable ConnectedElectricity ConnectedNatural Gas AvailablePropaneSewer ConnectedSolarSprinkler WellStreet LightsWater Connected Yrs Of Owner Prior To Leasing Re No Zoning RSF1


Listing information © 2026 My Florida Regional MLS DBA Stellar MLS..
Listing provided courtesy of MICHAEL SAUNDERS & COMPANY: 941-951-6660.



© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-04-12T21:44:01.643.
 
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