Set on five flat, impeccably landscaped acres at the end of a quiet cul-de-sac, this stately Georgian brick estate represents one of the most private and desirable settings within Upper Brookville's prestigious gated Colonial Drive enclave. Positioned on a private road of distinguished luxury estates and further enhanced by its own secondary gated entrance, the property offers a rare double gated level of security and exclusivity. A grand double height foyer welcomes you, anchored by a magnificent Baccarat chandelier, immediately setting a tone of timeless elegance. The home is thoughtfully designed for both grand scale entertaining and comfortable everyday living, featuring 4 fireplaces, a formal living room, elegant dining room, refined library, and a luxury bar area. The main level includes two bedrooms with two full bathrooms nearby, ideal for guests or extended living, along with a fully equipped laundry room. At the heart of the home, the sun-drenched chef's kitchen is enhanced by skylights and oversized custom windows, creating a bright and inviting atmosphere. Completed with premium appliances including a double wall Wolf oven, Wolf gas cooktop, and two Bosch dishwashers, breakfast nook and two pantries. The space seamlessly connects to the main living areas and opens to the patio, where retractable awnings provide effortless indoor to outdoor living. Upstairs, four spacious en-suite bedrooms include a luxurious primary suite featuring its own fireplace and a spa-inspired bath, offering a true private retreat. A Juliet balcony giving a view of serene front outdoor space. A finished attic adds a versatile open space suitable for a variety of lifestyle needs. The outdoor grounds are equally exceptional, showcasing expansive flat land, a heated gunite pool, tennis court, and multiple areas for entertaining and al fresco dining, all set within one of the most picturesque locations on Colonial Drive. Additional highlights include a finished basement with extra high ceilings, a whole house surround sound system, a recently updated roof (approximately 4 years old), and newer windows (approximately 1 year old). Updated Kitchen and bathrooms. Custom-made furnishings imported from Italy are included, further elevating the home's refined aesthetic. This extraordinary estate seamlessly blends classic Georgian architecture with modern upgrades, offering unparalleled privacy, scale, and sophistication in one of the North Shore's most coveted locations.