Set on 1.19± acres overlooking Fresh Pond, this traditional offers privacy, an elevated position overlooking the water, and southwest-facing light with sunset views. Largely hidden from the road, the property enjoys a quiet setting above one of Shelter Island's treasured glacial freshwater ponds. A gravel circular drive approaches the cedar-shingled façade, framed by established landscaping and gabled rooflines. The interior has been updated in 2026, including refinished floors, renovated bathrooms, refreshed exteriors and freshly painted interiors. A gracious entry is framed by a covered porch and a central Palladian-style window above the front door, bringing natural light into the foyer and halls. The double-height living room is imbued with natural light from a wall of windows and glass doors, creating an open yet grounded gathering space centered on a fireplace with custom built-ins. Above, a connecting balcony spans the room, linking the upper level while maintaining a sense of separation between the bedroom wings. The kitchen includes a center prep island and a breakfast bar, with an adjacent dining area facing the pond. A laundry room and powder room are set just off the kitchen, with convenient access to the attached two-car garage. The first-floor primary bedroom includes a renovated bath and walk-in closet. Upstairs, two additional bedrooms reflect the home's architecture, with varied ceiling lines that add dimension. The lower level has a finished office with separate entrance and an unfinished area with waterside windows that are ready for finishing. Outdoor amenities include a hot tub overlooking the water and a screened gazebo positioned for relaxed afternoons or casual gatherings. A path leads down to the pond and dock, offering access to the shoreline and the surrounding landscape.