Refined and elegant Circa 1927 Colonial, nestled on one of Chappaqua’s most coveted streets, exudes timeless charm while offering modern comforts. Ideally located just minutes from train station and town, with direct sidewalk access for easy walks to the heart of Chappaqua, this meticulously maintained and tastefully updated home, combines the best of both worlds -- generously scaled rooms that are both gracious and functional. The home’s period details, including hardwood floors, exquisite millwork, three fireplaces and built-ins, are complemented by modern updates. Formal living and dining rooms are perfect for sophisticated gatherings, while the expansive open kitchen and family room offer an inviting space for casual entertaining. The chef’s kitchen is a standout, featuring top-of-the-line appliances such as a Viking 6-burner range with griddle, Bosch dishwasher, GE Monogram refrigerator, and GE Monogram Advantium microwave/speed convection. The spacious center island with counter seating and prep area is ideal for both cooking and socializing, and the adjoining dining area offers the perfect setting for family meals. At the heart of the home, the family room features a striking raised hearth stone fireplace and French doors that open to a large deck overlooking bucolic, private grounds. The thoughtfully landscaped gardens, stone walls, and level play areas create a serene outdoor oasis, with a magnificent heated pool as the centerpiece. Whether you’re relaxing by the pool, entertaining on the rear deck, or enjoying the covered stone patio and porch, the outdoor spaces are perfect for year-round enjoyment. The second and third floors offer spacious and comfortable accommodations, including a primary bedroom suite with en-suite bath, three additional bedrooms, and a full bath. A versatile office/bedroom is ideal for remote work, full bath, and a second bedroom/bonus room on the third floor is perfect for a guest room, gym, art studio, or 2nd family room. The amazing finished lower level with radiant heated floors includes a media room and a billiard/recreation room with fireplace and wet bar, both of which lead to the covered stone surround porch, a laundry room, pantry with second refrigerator, and a mudroom with dog bath and door to the one and a half car garage. Sited on over an acre of wonderfully manicured grounds, the property is adorned with specimen trees, vibrant flowering gardens, and an expansive lawn. NEW special features include: A/C compressors, oil tank, driveway, washer/dryer, ADT home security system, refrigerator, dishwasher, new electric box for portable generator which runs 80% of house, cedar and split rail fences. Other features: Irrigation system, in ceiling indoor and outdoor speakers, dog bath and more. A rare find in Chappaqua, This quintessential and VERY SPECIAL home is a RARE FIND and a must see! Seller won't vacate before June 2026 but would consider closing earlier with a rent-back.