Under contract-accepting backup offers. Discover coastal luxury in the prestigious, 24-hour guard-gated Bay Isles Bayou community on Longboat Key. Tucked away on a quiet cul-de-sac, this executive-style home sits on nearly a third of an acre, surrounded by lush tropical landscaping and mature oaks. Boasting over 3,500 square feet of refined living space, this 4-bedroom, 4.5-bathroom residence offers an inviting blend of elegance and comfort. A pavered driveway leads to a spacious three-car garage, with a private carriage house suite above--ideal for guests or extended stays. Inside, crown molding and tray ceilings enhance the expansive living room, where a designer fireplace and feature wall create a striking focal point. Warm hickory hardwood floors span the main level, with oversized Carrera tile adding a sleek touch to the kitchen. The open-concept kitchen is a chef's dream, featuring a large island, breakfast bar seating, custom cabinetry, modern granite countertops, a glass tile backsplash, and top-of-the-line stainless steel appliances, including a Wolf range. A built-in wet bar with ample storage and dual beverage coolers enhances the space, perfect for entertaining. The primary suite, located on the first floor, is a serene retreat with a tray ceiling, private lanai access, a generous walk-in closet, and a luxurious ensuite with dual vanities, a walk-in shower, and a soaking tub. Two oversized guest suites, each with beautifully designed bathrooms, and a versatile den complete the main level. A well-appointed indoor laundry room offers ample storage and counter space. Designed for seamless indoor-outdoor living, a wall of sliding glass doors opens to the screened lanai, where a resort-style pool and spa set the stage for relaxation. The outdoor kitchen, equipped with granite countertops, a farm sink, a premium gas grill, and a mounted flat-screen TV, makes entertaining effortless. A convenient pool bathroom adds to the thoughtful layout. As a resident of Bay Isles, enjoy exclusive access to the Bay Isles Beach Club, a private, residents-only retreat with pristine sandy shores, a picnic area, restrooms, and dedicated parking. Situated near the Publix shopping plaza and just moments from the world-class dining and boutiques of St. Armands Circle, this exceptional home also offers easy access to Sarasota's vibrant cultural attractions. Whether you're looking for a private coastal sanctuary or an entertainer's dream home, this Longboat Key masterpiece delivers the best of Florida living.