Elegant and sophisticated, shingle style Colonial sited on 3.46 acres of level, idyllic, private property in one of Chappaqua's most coveted neighborhoods. A private, gated drive introduces this 5 bedroom, 8,000+sq ft home, built by the renowned McKenna Associates, known for quality construction and meticulous workmanship. Designed with luxury finishes and amenities, this home combines both elegance and comfort boasting gleaming hardwood floors, custom millwork, stone fireplaces and more. An impressive double height entry foyer with a sweeping circular staircase opens to formal spaces, a large study, a gourmet Chef's kitchen with radiant heated floors, top-of-the-line appliances (2 Thermador ovens, Bosch dishwashers, Viking 6-burner range with griddle, SubZero, refrigerator), a huge island with counter seating, breakfast room and doors to an expansive deck overlooking the idyllic rear yard, a butler's pantry with icemaker, warming drawer and prep areas, and an expansive family/great room boasting an impressive floor-to-ceiling stone fireplace. The upper level offers a private primary suite with dressing room, two large walk-in closets, and spa bath with radiant heated floors and steam shower. The primary suite also has a walk up loft space currently fitted as a custom closet. Three very large bedrooms, all with their own baths, and an upstairs laundry complete this level. A staircase off the second level leads to a loft area perfect for play/homework or office and access to the enormous attic for amazing storage (and future finished space, if wanted). The home is completed by an expansive walkout lower level with a large recreation room, a walk-in temperature controlled wine room, an office/guest room, 2 full baths, homework/desk area, multiple storage areas and pristine mechanical room. The level backyard (with probable pool site) is perfect for play or entertaining. This Whippoorwill neighborhood home is sited on exquisite property with stone walls and rolling lawns. NEW Roof July 2024, whole house Briggs Stratton generator, electric vehicle charger, whole house audio system, Wifi thermostats, heated garage with epoxy flooring and more! Minutes to town and schools. 50 minutes to NYC. An EXCEPTIONAL Chappaqua offering! Additional Information: Amenities:Dressing Area,HeatingFuel:Oil Above Ground,ParkingFeatures:3 Car Attached,