There is a quieter side of Anna Maria Island that not everyone experiences. At 242 Oak Avenue, life unfolds in a way that feels entirely your own. Tucked away from the crowds, this rare waterfront retreat is designed for stillness, privacy, and uninterrupted views across Bimini Bay. With no neighboring rooftops competing for your attention, the setting is defined by open water, coastal breezes, and the natural rhythm of island life. Positioned on a remarkable triangular parcel with over 500 feet of water frontage, this gated, elevated residence offers water views from every room. The open concept design creates a seamless connection between indoor and outdoor living, anchored by a dramatic great room with vaulted ceilings and expansive glass doors that disappear into the walls, opening to an oversized covered lanai. The chefs kitchen is thoughtfully designed with custom imported cabinetry and distinctive finishes, flowing effortlessly into both formal dining and outdoor entertaining spaces. Just beyond, the lanai becomes a true extension of the home, complete with a full outdoor kitchen, Teppanyaki dining, fire table, lounge areas, and a whirlpool spa, all set against panoramic bay views. The main residence features two luxurious primary suites with private ensuites, while a separate guest house, connected by a covered bridge, offers two additional bedrooms, a full bath, and kitchenette, creating an ideal private retreat for family and guests. Outdoor living continues at every level. A resort style pool with fire and water features is surrounded by lush tropical landscaping, leading to a private waterfront fire pit along your own sandy shoreline. For boating enthusiasts, the property is equally exceptional, featuring a 60 foot dock, 12,000 lb. boat lift, and direct access to Tampa Bay and the Gulf of Mexico. Now offered with a significant $500,000 price adjustment, this is a rare opportunity to secure one of the islands most distinctive waterfront estates. This pricing opportunity is available for a limited time through April 15, 2026.