This West Indies-inspired estate combines timeless craftsmanship with modern upgrades for unparalleled comfort and self-sufficiency. High Watch is a hilltop fortress perched atop a level, landscaped .693 acres, its one-of-a-kind wraparound porch-supported by 40 concrete columns and 20 arches-offers panoramic views of Frenchman's Bay, Buck Island, and the western ocean. The property is equipped with a 2-bedroom, 2-bath main house, a 1-bedroom loft-style casita, and a sparkling saltwater pool at the center. The single-level layout boasts a spacious great room with three French doors that open to the expansive porch, allowing cooling easterly breezes to flow through the home. Recent upgrades reflect meticulous care and thoughtful investment throughout the property: a brand-new 14KW Perkins/Cummins whole-house generator, a handyman's dream workshop/shed, and a solar power system featuring 28 ProSolar panels and 3 Tesla Powerwalls. The restored saltwater pool system with high-efficiency equipment, a circular gravel driveway, and lush, purposeful landscaping further enhance the property's seamless blend of beauty and utility. This stouthearted, self-sufficient home has consistently stood the test of time, with attention to detail evident in both design and function. For those seeking a turnkey transition, additional amenities are available for negotiation to ensure a seamless move: a 90-gallon backup diesel tank, a Ford F-150, a golf cart, and an ATVall the essential pieces already in place to support comfort, mobility, and efficiency from day one. Come check out this incredible property!