Set at the end of a secluded private drive, this stunning shingled Colonial estate sits gracefully atop a hill overlooking the Long Island Sound. Offering an unparalleled vantage point and exceptional privacy, this waterfront property unfolds as a true compound - complete with a Har-Tru tennis court, sparkling in-ground pool and spa, elegant pool house, main residence, and a detached garage with a fully appointed studio apartment. Originally built in the 1950s, this designer home blends grand scale with timeless charm and warmth. Throughout, you'll find wide-plank hardwood floors, river rock stone fireplace, and expansive windows that flood the interiors with natural light. A picturesque foyer opens to the gracious great room, designed for both living and dining, while the custom eat-in kitchen impresses with thick-cut marble countertops, chef-grade appliances, and a spacious walk-in pantry. Most formal living spaces offer captivating water views, and a series of French doors seamlessly connect the indoors to the home's stunning outdoor entertaining areas. The main level also includes a private office, large den, and two luxurious powder rooms. Upstairs, a mezzanine leads to the sun-drenched Primary Wing, featuring a generous bedroom with sitting area, two walk-in closets, and a spa-like bath with a sizable therapeutic shower and freestanding soaking tub. Four additional bedrooms complete the upper level - two with private en-suites and two connected by a Jack-and-Jill bath. The finished, walk-out lower level offers exceptional recreational space, including an art studio, media/theater room, game room, full bathroom, laundry room and a matted, glass-enclosed fitness area. The grounds are nothing short of spectacular - a total of 4.5+ acres framed by mature landscaping, stone walls, and slate patios. Outdoor living is elevated with a built-in kitchen, expansive sundeck surrounding the pool, and a newly renovated pool house complete with a changing room, great hosting space, and kitchenette. A detached garage with a second floor apartment, adds flexibility for guests or staff. Additional features include two laundry rooms, a long circular stone driveway and dual garages providing a total of four parking spaces. A curved stone terrace offers an elevated vantage point over the backyard amenities and shoreline. At the end of the property is a private wooden boardwalk that meanders through lush greenery and coastal vegetation, leading to your own sandy North Shore beach. This extraordinary home masterfully combines sophistication, comfort, and waterfront living at its finest.