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 Keys 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 Higels early 20th century Higelhurst Hotel, the pioneering developers 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 homeowners 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 butlers 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 chefs 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 homes 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.