This soaring light filled home blends gently onto a majestic waterfront bluff, one of the highest points on Shelter Island centrally located above Crescent Beach - a perfect viewing spot for the annual Shelter Island Fireworks! Surrounded by almost four acres of wooded privacy, the property offers sweeping water views across the North Fork and beyond to the Connecticut shoreline, with glorious year round sunsets. Designed by architect Michael Haverland, the residence is a hybrid of a 1925 Shelter Island traditional beach house, juxtaposed perfectly with a 3400 square foot modern addition, for a total of over 6000 square feet of living space. Two elegant wings come together, their pitched roof lines and mullioned walls of glass blending seamlessly with the style of the original beach house. Delicate steel window frames are detailed as thin as possible, providing an abundance of natural light, allowing magnificent water views. The northwest facing bedroom wing provides separation and privacy from the rest of the house. The master bedroom suite's exposed steel beams support a vaulted ceiling with a full window wall of endless views. A second bedroom suite below with floor to ceiling windows offers similar stunning vistas. Both master and guest suites have attached dressing rooms. Each features a generous size stone and tiled bathroom complete with a luxurious soaking tub, glass enclosed shower and oversized wall hung double sinks. The living room wing faces north and west, also with exposed structural steel columns and beams serving as a counterpoint to a 23' gabled wall of glass. Polished limestone flooring balances with a two story fieldstone fireplace, customized with an inset flat screen for relaxing evening enjoyment. An inviting entrance foyer greets visitors with views through to the water, and serves to transition the modern to the original house, which has been extensively renovated.The 1925 living and dining room have been combined into an expansive dining room. With a wood burning stone fireplace reaching to the top of the cathedral ceiling, the room opens to an all season enclosed porch featuring a custom wood banquette for breakfast and casual meals. A gourmet kitchen combines classic white cabinetry with long butcher block countertops, and white matte finish Viking appliances, including a 48" stove with double ovens, oversize refrigerator, and two dishwashers. An additional three bedroom / office combination, a guest suite with private expansive bathroom, plus an additional bathroom and powder room provide ample room for family and friends. The lower level of the compound includes an additional bedroom with full bathroom, game room, climate-controlled gym, full size freezer and laundry room. For the exotic car enthusiast, the three car garage is heated and has central air. A central sound system runs throughout the entire house and outdoors. The landscaped exterior is perfect for outdoor relaxation. Large stone terraces and a high roof deck between the new and old wings on the 3rd level easily accommodate entertainment on almost 320' of water view frontage. The outdoor dining area can be covered by a movable awning for shade or showers. The cornerstone of this unique property is perhaps the most dramatic infinity edge gunite pool on the entire east end of Long Island - bar none! With water views as you swim, expansive limestone and teak surround, outdoor Viking kitchen with grill and refrigerator, steps to an outdoor poolside shower, as well as to a full bath and dressing area. Beautiful old trees dot the property, which is set back from the road on a gravel drive in a desirable area nearby to Sunset Beach Restaurant, Perlman Music Program, boating, tennis and golf. An outdoor basketball court and fire pit round out the amenities. And as part of a small community association, there is a stretch of private beach and two docks, just a short walk down a path. A one of a kind opportunity! 7.75m