Under contract-accepting backup offers. Welcome to the secure, double-gated Bay Isles Bayou community on Longboat Key. Set on an exclusive waterfront lot just two houses down from the open waters, this extraordinary estate boasts over 5,700 square feet of refined living space, capturing breathtaking west-facing views over Buttonwood and Cranes Bayou. Step inside to soaring 20-foot ceilings, a magnificent crystal chandelier, and an inviting formal great room adorned with custom built-ins and a stately fireplace--each detail reflecting the grandeur and grace of this one-of-a-kind residence. This home features four expansive bedrooms, four full baths, and two half baths, along with an updated hydraulic elevator for seamless access to every level. The heart of the home is this chef's kitchen that features quartz and granite countertops, exquisite European-style cabinetry, and top-of-the-line Wolf and commercial-grade appliances. A spacious center island with a prep sink provides ample workspace, while stunning water views elevate every culinary experience. The owner's suite is a true private retreat, offering separate baths and an astonishing 300+ square foot walk-in closet. A private staircase leads to the primary office, where walls of windows frame sweeping bayfront panoramas--an inspiring space for work or quiet reflection. A modern spiral staircase with glass railings leads to the second level, where two additional en-suite bedrooms and a sprawling den await. Added in a 2011 renovation, the den features floor-to-ceiling bayfront windows, a private half bath, and access to the upper-level sunset terrace--the ultimate sanctuary to soak in the Gulf's radiant hues. Designed for true indoor-outdoor living, the fully enclosed lanai features electric retractable screens, a spa-like pool with an elevated hot tub, and sweeping water views that are the perfect backdrop for sunset soirees.. Boating enthusiasts will delight in the oversized dock, equipped with a 10,000-lb boat lift and a 2,000-lb hoist for jet skis or other water toys, ensuring effortless access to Longboat Key's world-class waterways. Beyond its breathtaking beauty, this home offers peace of mind and lasting quality, with recent upgrades including a newer roof, all-impact windows and doors throughout, a whole-house automatic generator, all-new AC units, a private well for irrigation, and new hot water heaters--ensuring effortless luxury for years to come. As a Bay Isles resident, you'll enjoy exclusive access to the Bay Isles Beach Club, a private Gulf-front oasis. Nearby, the Longboat Key Club offers championship golf, award-winning tennis, a Gulfside pool deck, a state-of-the-art fitness center, spa services, and fine dining, along with a full-service marina for yachting enthusiasts. Stroll or bike to Publix, the public tennis center, town hall, the library, and local art shows at the Caron Family Pavilion. Just a short drive away, indulge in the luxury shopping and culinary delights of St. Armands Circle, the cultural energy of Downtown Sarasota, and the convenience of Sarasota International Airport. This grand waterfront residence offers an unrivaled price per square foot--a rare opportunity in this highly coveted enclave. While a discerning buyer may wish to personalize some cosmetic details, the most critical and costly updates have already been addressed, ensuring seamless, stress-free luxury living. Here, at the water's edge, coastal dreams come to life. This is more than a home--it's a lifestyle.