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DockOnly™ and Dock Score™ are trademarks of Blue Mar Real Estate Group Inc.

Blue Mar Real Estate Group Inc. — Licensed Florida Real Estate Broker

Blue Mar Real Estate Group Inc.

Licensed Florida Real Estate Broker · DBPR License CQ1018554

4000 Ponce De Leon Blvd, Suite 470, Coral Gables, FL 33146

[email protected]

Listing data is provided by participating Multiple Listing Services and is deemed reliable but not guaranteed. Each listing's MLS source and its required disclosures appear with that listing. Dock Score™ is a DockOnly.com rating and is not provided by or affiliated with any MLS or listing broker. NOAA chart data is public domain and for reference only — not for navigation. Full MLS Compliance

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+20

3440 GULFMEAD DRIVE

SARASOTA, FL, 34242

Active

$12,900,000

3440 GULFMEAD DRIVE

SARASOTA, FL, 34242

Active

$12,900,000

5

Bedrooms

6

Bathrooms

6,596 sqft

Living Area

2008

Year Built

$12,900,000Tour the dockSchedule a Showing
Navigation note: Navigation routes show the shortest mapped path to open water. A vessel taller than the binding bridge clearance may still reach open water via a longer alternate route that we don't currently map — verify navigability with a local captain or surveyor before relying on it.

31,293

Lot Size (sqft)

138

Days on Market

Dock Score™

DockOnly
46
Fair

What shaped this score

✓Bridge-free to bay & ocean
✓Dock with boat lift
✓Fits boats up to ~85ft (est.)
·Waterfront

DockOnly.com rating — not provided by the MLS or listing broker.

Dock & Water AccessMLS

Gulf/Ocean📝 22K-lb boat lift📝 deep water

AI Aerial Imagery Detection

Dock DetectedBoat Lift DetectedDeep Water Indicators~72-98 ft dock

Detected by AI from open-source aerial mapping imagery and may not reflect current conditions. This information was not provided by the MLS or listing broker. Always verify dock infrastructure with the listing agent.

Navigation RouteDockOnly

Data sources: SFWMD AHED waterway polygons · FHWA National Bridge Inventory 2024 · Not provided by the MLS or listing broker.

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. Photos 1 and 2 reflect the new colors that the home is being painted.

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Location

SARASOTA, FL, 34242

No price history available for this property.

Displayed by Blue Mar Real Estate Group Inc. — Licensed Florida Real Estate Broker (DBPR CQ1018554) · [email protected]

Listing courtesy of MICHAEL SAUNDERS & COMPANY via Stellar MLS

Last updated: 6/23/2026

© 2026 Stellar MLS. All rights reserved. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange (IDX) program of Stellar MLS. Information is deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change, or withdrawal.

IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Dock Score™

DockOnly
46
Fair

What shaped this score

✓Bridge-free to bay & ocean
✓Dock with boat lift
✓Fits boats up to ~85ft (est.)
·Waterfront

DockOnly.com rating — not provided by the MLS or listing broker.

FEMA Flood Zone AE
BFE: 7ft

Special Flood Hazard Area

View FEMA Flood Map →
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Mortgage Calculator

Estimate your monthly payment for this waterfront property

20%

$2,580,000 down

%
Principal & Interest$66,935/mo
Property Tax (est. ~1.2%, varies by county)$12,900/mo
Home Insurance (est.)$250/mo
Total Monthly Payment$80,085
Loan Amount: $10,320,000Rate: 6.75%
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Estimated payments only. Actual rates and terms may vary.

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