Originally the gardener's cottage of the historic Constable Estate, this exceptional Shingle-Style residence set on .36 acre on prime coastal block of Orienta Point seamlessly blends its 1861 heritage with thoughtful modern updates. A meticulous 2010 down-to-the-studs interior and exterior renovation introduced all-new cedar shingle siding, cedar shake roof, new wood burning fireplace with chimney, plumbing, electrical, and mechanical systems, while reclaimed antique hardwood floors and new Le Page leaded glass windows pay homage to the home's original craftsmanship at every turn. Enter through a radiant-heated foyer to unveil soaring 10.5ft ceilings throughout, where barn doors reveal a spacious living room centered around the wood burning fireplace. A full bath with steam shower on the main level adds everyday luxury. The family room, highlighted by an exposed brick decorative fireplace, offers a warm and inviting retreat, while the cherry wood and black granite kitchen-equipped with high-end appliances-balances style and functionality. A sunlit formal dining room, which could also be used as a family/playroom, with coffered ceiling opens to a charming deck overlooking the rolling front lawn. At the rear, the living spaces extend to a private bluestone patio set against the original stone boundary wall of the Constable Estate-an idyllic setting for alfresco dining and quiet evenings beneath mature trees. Upstairs, the primary suite offers a serene escape, featuring a sitting room or private study with a decorative fireplace that flows into a generous bedroom with a skylit bath and access to a private balcony with views of Long Island Sound. Two additional well-proportioned bedrooms share an updated hall bath on the second level. The home's elevated position enhances its striking curb appeal and affords water views from the upper-level rooms, just one street from the Sound. An unfinished lower level and full attic-accessed via a drop-down ladder with a rooftop hatch leading to a large, private deck with 360 degree panoramic views of the sound-provide substantial additional flex space. An attached two-car garage completes this rare offering. Rich in history yet fully reimagined for modern living, the home is ideally located in the coveted Orienta Point neighborhood, moments from the harbor, beach, and yacht clubs, and just minutes to Mamaroneck village and Metro-North for an easy commute to New York City.