Set amid 40+ reserve acres of waterfront privacy, this 10,000+/- sq. ft. custom home on 1.85+/- serene acres includes the latest green building features, advanced technology and all the modern amenities one would desire. Upon arrival, the home presents itself as an evolved traditional with modern interiors and comfortable classy feel. The home's many large custom windows and glass doors afford intimacy with nature, the surrounding waterways, and the magnificent sunsets. The home provides eight bedroom suites plus two additional full baths and two powder rooms. First floor living areas flow seamlessly - the great room is highlighted by a 6' gas fireplace and a wall of glass doors overlooking Shelter Island Sound, the waterside 62' saltwater pool with 12 person spa, 2,500+/- sq. ft. stone terrace, a fire pit and summer kitchen. A superb chef's kitchen features custom cabinetry, large center island, butler's pantry, walk-in food pantry, coffee bar, breakfast area and top of the line appliances. Adjacent is an indoor/outdoor family room with radiant heated floor, retractable glass doors, gas fireplace and full poolside bath. There is also a formal dining room with estuary views and a private junior master suite with terrace access. A three-car radiant heated garage includes a car lift, two EV charge stations and a restricted service entrance. The first level also includes a laundry room. You enter the second level into the light-filled gallery. The spacious four room master suite has a gas fireplace, retracting glass wall opening to a private waterfront outdoor lounge, and large walk-in closet with wet bar and linen closet. The grand marble-walled bath contains an open double shower, soaking tub, double custom vanities, separate water closet and outdoor shower. The second level also includes four bedroom suites and a laundry room. The finished lower level features wood flooring, a gym with steam shower, spa bar, sauna and powder room. The entertainment room has a theater, full bar and billiards area. There are two windowed en-suite bedrooms adjacent to a lower level den. A wine room completes this fully utilized level. All levels are accessible via the three-level elevator.