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 of Mexico to the calm shores of Lemon Bay, offering an extraordinary 155 feet of direct Gulf frontage, 155 feet of bay frontage, and nearly 299 feet of depth-creating an exceptional, compound-sized setting. The property captures sweeping, unobstructed water views, spectacular sunsets over the Gulf, and tranquil sunrises across Lemon Bay. Cherished by the same family for almost 30 years, this legacy residence offers 5 bedrooms, 4 bathrooms, and 4,033 square feet of living space. The layout includes a 3-bedroom, 3-bath main home (3,073 sq ft) and a private, independent 2-bedroom guest apartment above the garage (960 sq ft) with its own living room, providing ideal flexibility for multi-generational family, long-term guests, or a caretaker suite. Designed to embrace the outdoors, multiple windowed doors open to the pool, beach, bay, and surrounding grounds, creating seamless indoor-outdoor living. The main living area features dramatic cathedral ceilings, warm cypress accents, custom built-ins, surround sound, and sliding glass doors leading to the screened pool area. A bayfront dining room is perfectly framed by high-end Andersen windows to capture the morning light, while the premium kitchen enjoys direct water views from the sink, featuring solid wood cabinetry, a Thermador cooktop, GE double ovens, a GE Monogram refrigerator, two pantries, and breakfast bar seating. Outdoor living is at the heart of the home, showcasing a heated pool and an expansive 18x48 open lanai just steps from the sand. On the bay, a private dock re-decked in 2025 (89 feet long) is fully equipped with water, electric, and a fish cleaning station, allowing for convenient boating along Lemon Bay and immediate, deep-water access through Stump Pass to the Gulf. Beyond the premier location, the estate provides incredible peace of mind and major capital improvements. Highlights include an elevation of ~12.9 feet, a 2021 metal roof, full impact windows and doors, three newer AC systems (2018, 2022, 2023), a septic system replaced in 2016, modern PVC plumbing, and a brand-new 2025 pool cage. The fully fenced property enhances privacy while preserving the stunning, panoramic coastal views. From your private dock, curate the perfect day on the water by heading south through Lemon Bay and tying up at local waterfront favorites, including Beachcomber Trading Post, The Lighthouse Grill, or Magnolias on the Bay for lunch, and The Waverly Restaurant & Bar for evening cocktails before continuing through Stump Pass into the open Gulf. Located along one of the most desirable, pristine stretches of Manasota Key, this exceptional property offers a rare combination of dual waterfront scale, absolute privacy, superior boating access, and breathtaking natural beauty. Options: Manasota Key Club offering pickleball, bocce, tennis, a community pool, fine dining, walking paths, and vacation cottages for guest rental. And Hermitage Artist's Retreat: a renowned incubator for diverse, original works across all artistic mediums, hosting global artists right on Manasota's Gulf-front campus.