$13,950,000

.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… Read More 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. Read Less

Courtesy of MICHAEL SAUNDERS & COMPANY 941-951-6660

Listing Snapshot

Days Online

Last Updated

Feb 6, 2026

Property Type

Single Family Residence

Beds

Full Baths

Partial Baths

Square Ft.

6,596

Lot Size

0.72 Acres

Year Built

2008

MLS Number

A4679384

Additional Details

Appliances & Equipment

Dishwasher, Bar Fridge, 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, Other equipment: Irrigation Equipment

Property Access

Road Surface: Asphalt, Paved

Building

Built in 2008, Living area: 6596, Living area units: Square Feet, Building faces East, 3 stories, Levels: One, Construction Materials: Block, Concrete, Stucco

Community

Street Lights

Cooling

Central Air, Zoned

Energy Saving

Energy Efficiency: Insulation, Water Heater, Windows, Energy Generation: Solar

Exterior Features

Patio/Porch Features: Covered, Enclosed, Rear Porch, Screened, Side Porch, Wrap Around, French Doors, Lighting, Outdoor Shower, Rain Gutters

Fence

Fenced

Fireplaces

Living Room, Wood Burning

Floors

Brick, Wood

Foundation

Stilt/On Piling

Garage

6 spaces

Heating

Central, Electric, Zoned

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

Laundry

Electric Dryer Hookup, Inside, Laundry Room, Washer Hookup

Lot

0.72 acres, Dimensions: 100x298, FloodZone, City Limits, Landscaped, Street Dead-End, Paved, Mature Landscaping, Trees/Landscaped

Parking

Tandem, Workshop in Garage

Pets Policy

Allowed: Yes

Pool

In Ground, Lap, Salt Water

Property

Completed, Water

Roof

Metal

Security Features

Closed Circuit Camera(s), Fire Alarm, Security System, Security System Owned, Smoke Detector(s)

Sewer

Public Sewer

Taxes

Additional parcels description:, Parcel Number: 2019060040, Public Survey Range: 17E, Public Survey Section: 36, Annual Amount: $58,420.5, Tax Book Number: 5-66, Legal Description: LOT 3, GULFMEAD ESTATES, Lot: 3, Year: 2025, Zoning: RSF1

Utilities

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

Water Features

Water Body Name: BIG PASS, Gulf/Ocean

Windows

Drapes, Rods, Storm Window(s)

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