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 two hundred feet south of civic leader Henry Higel's early twentieth-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-homeowner's meticulous eye for detail. Constructed on pilings and grade beams, the home is set on a thirty-one thousand two hundred ninety-three-square-foot lot and encompasses six thousand five hundred ninety-six square feet under air, with more than thirteen thousand 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 walk-in pantry opening to casual dining spaces as well as sun-filled outdoor porches. Upstairs,the primary suite is a tranquil retreat featuring spa-inspired bath oversized walk-in closet shaded terrace,and outdoor shower.The expansive dock features two boat lifts: one twenty-two thousand-pound lift suitable for a thirty-two- to thirty-six-foot vessel anda second ten-thousand-pound lift.A humidity-controlled four-car tandem garageanda separate two-car garage accommodate up to six vehicles alongwith extensive marine andrecreational gear.Solar panels anda thirty kilowatt generatorunderscorethe home's focuson energy efficiencyand resilience.Outdoor living is highlightedbya twenty-thousand-gallon heated saltwater lap pool surrounded by Shellcrete patiosand Ipe decking.A perched beachwith fire pitandswings welcomes gatherings overlookingBig Pass whilea seventy-five foot rear setbackensures privacywithin alushly landscaped yard.Rich in history,resilientand luxurious,intimateand refined,thisis Sarasota waterfrontliving at its most authenticand coveted.