Breathtaking Gulf-to-Bay living awaits on the coveted, private north end of Manasota Key. This rare beachfront estate spans from the turquoise waters of the Gulf to the calm shores of Lemon Bay, offering approximately 155 feet of direct Gulf frontage, 155 feet of bay frontage, and nearly 299 feet of depth, creating an extraordinary setting that is increasingly difficult to find. With ownership extending to the mean high water line, the property captures sweeping water views, spectacular sunsets over the Gulf, and tranquil sunrises across Lemon Bay. Enjoyed by this family for almost 30 years, the residence offers 5 bedrooms, 4 bathrooms, and 4,033 square feet, including a 3 bedroom, 3 bath main home (3,073 sq ft) and a private 2 bedroom guest apartment above the garage (960 sq ft) with its own living room, providing ideal flexibility for family and guests. Designed to embrace the outdoors, multiple windowed doors throughout the home open to the pool, beach, bay, and surrounding property, allowing natural light to fill the interior while creating seamless indoor-outdoor living. The living room features cathedral ceilings, cypress accents, built-ins, surround sound, and sliding glass doors leading to the screened pool area. A bayfront dining room is framed by Andersen windows, while the kitchen enjoys water views from the sink and offers Corian countertops, wood cabinetry, Thermador cooktop, GE double ovens, GE Monogram refrigerator, and two pantries with breakfast seating. Outdoor living is at the heart of the home with a heated pool, expansive 18x48 open lanai, covered grilling area, and spacious entertaining areas just steps from the sand. On the bay side, a private dock re-decked in 2025 (approx. 89 ft long) with water, electric, and fish cleaning station allows convenient boating along Lemon Bay and access through Stump Pass to the Gulf. Additional highlights include a 2021 metal roof, impact windows, impact doors, three AC systems (2018, 2022, 2023), septic system replaced in 2016, PVC plumbing, pool cage 2025, and a baseline elevation of approximately 12.9 feet. The fully fenced property enhances privacy while preserving the stunning coastal views. From the dock, curate the perfect day on the water by heading south through Lemon Bay and tying up along the way at local waterfront favorites including Beachcomber Trading Post for breakfast, The Lighthouse Grill or Magnolias on the Bay for lunch or sunset dining, and The Waverly Restaurant & Bar for cocktails before continuing through Stump Pass into the open Gulf for an unforgettable evening on the water. Join the optional Manasota Key Club for additional amenities such as: pickleball, bocce ball, fine dining, tennis courts, community pool and vacation cottages that can be rented, along with great walking paths. See attachments for details. Check out the Hermitage Artist's Retreat as well, an incubator for diverse and original works across all artistic mediums, who host accomplished and diverse artists on Manasota's very own Gulf-front campus! Located along one of the most desirable stretches of Manasota Key, this exceptional property offers the rare combination of dual waterfront, privacy, boating access, and breathtaking natural beauty-where mornings begin with dolphins offshore and evenings end with unforgettable Gulf sunsets.