There is nothing like this on Lake Winnipesaukee. Offered together as a private Winter Harbor compound, 14 & 20 Gateway Road encompass approximately 3 acres +/- with approximately 370' +/- of combined waterfront, two residences, extensive docking, and a sandy walk-in beach. The centerpiece, completed in 2023, is an approximately 8,600-square-foot contemporary residence was engineered by Thornton Tomasetti. Brazilian black slate and engineered rift oak floors, solid rift oak interior doors, hand-selected natural quartzite, custom millwork, stained red cedar siding, Douglas fir porch ceilings, and IPE decking define the build. A fully integrated Control4 system governs lighting, climate, Lutron power shades, and distributed audio. An 800-amp electrical service is supported by 45 kW generator backup. Six bedrooms, six full baths, three half baths, generous gathering spaces, and multiple professional-grade kitchen and prep stations support serious entertaining. At 20 Gateway, a cantilevered steel boathouse with rooftop entertaining deck is paired with a no-profile boat lift, 50-foot aluminum Lift-A-Dock, and sandy walk-in beach. At 14 Gateway, 195 feet of Winter Harbor frontage includes expansive U-shaped covered docking with room for multiple boats and watercraft. The classic 1958 Winnipesaukee cabin at 14 Gateway sits on approximately two additional acres and offers three bedrooms, one full bath, warm wood interiors, and a broad lakeside deck. More time capsule than guest house, it provides a distinct counterpoint to the contemporary residence. This is a finished, move-in-ready Winter Harbor compound that brings together contemporary architecture, a preserved vintage lake cabin, approximately 370' +/- of waterfront, extensive boating infrastructure, and approximately 3 acres +/- in one exceptional offering. Please note all acreage, waterfrontage, sq footage, bedrooms and baths have been combined to reflect the whole compound.