Tucked away on nearly 3-acres of rolling hilltop landscape and bordering over 28-acres of protected preserve, this newly renovated Shelter Island Harborview traditional is a rare sanctuary where timeless architecture meets breathtaking natural reserve and harbor views. Perched above Coecles Harbor with sweeping vistas stretching toward Ram Island, the home captures the elegance and charm that define life on Shelter Island. A gracious foyer welcomes you into interiors that feel both refined and inviting. Natural light moves effortlessly throughout the first floor, where thoughtful design and classic detailing create spaces meant for gathering. The expansive great room, that spans the width of the home, serves as the heart, framed by eaves on both sides and showcasing panoramic harbor views seamlessly blending living and dining areas beneath soaring ceilings.A wood-burning fireplace anchors the space, while French doors at both the front and rear open to bluestone patios, allowing for seamless indoor & outdoor entertainment. Just beyond, the chef's kitchen is equally impressive - a true gathering place featuring vaulted ceilings, a central island, breakfast nook, walk-in pantry, and its own wood-burning fireplace, creating an atmosphere that feels intimate yet grand. Nearby, a charming living room with ensuite full bath offer a quiet escape. The first-floor sleeping quarters are designed with comfort and privacy in mind. The primary suite enjoys a serene connection to the outdoors, opening directly onto a covered patio with tranquil harbor views. Inside, the primary suite also features a spacious walk-in closet and spa-like bath with shower and soaking tub. A separate en-suite guest bedroom with walk-in closet occupies its own private wing. Upstairs, 2-thoughtfully appointed guest rooms with a shared full bathroom. The second floor additionally features a bedroom and den with a half bathroom and sun filled oversized sitting room. The lower level enhances the home's lifestyle appeal with a recreation and billiards room, gym, and cedar walk-in closet - ideal for both leisure and practicality. Outside, beautifully landscaped rolling lawns dotted with mature trees create a peaceful park-like setting. At the center of it all lies a stunning 20' x 40' Gunite pool, surrounded by an expansive patio, open sky and preserved land, offering exceptional privacy and uninterrupted sunlight throughout the day.