NEW PRICE - $1,599,000! Exceptional value for a meticulously maintained 6,259 SF custom Colonial on 2.72 private acres in desirable Redding, CT. Privately set on a quiet cul-de-sac in sought-after Gallows Hill, 2 Longwood Drive offers the space, privacy, quality and flexibility sought by discerning buyers from Fairfield County, Westchester and NYC. Just 8 minutes to the Redding Metro-North station and approximately 1 hour 20 minutes to NYC by car, this quintessential New England country estate provides a peaceful retreat while remaining connected to the metropolitan area. Meticulously maintained by its original owner, this custom home features 9-14' ceilings, hardwood floors, generous room sizes and light-filled living spaces designed for both everyday living and sophisticated entertaining. The gourmet kitchen features Sub-Zero refrigeration, Wolf six-burner gas cooktop, granite countertops, custom cabinetry and a large center island, opening to a spacious family room with gas fireplace, wet bar and French doors leading to the outdoor living spaces. The spacious primary suite features two full bathrooms, abundant closets and a whirlpool tub, complemented by three additional bedrooms and generously sized baths. A standout feature is the finished third-floor private living space with a full ensuite bathroom and steam shower/sauna, offering exceptional flexibility as a 5th bedroom, au pair suite, in-law suite, private guest quarters, home office, gym, media room or retreat. The 5-bedroom septic system adds valuable flexibility beyond the home's current four-bedroom configuration. Additional highlights include a brand-new HVAC system, zoned central air, whole-house generator, thermopane windows and transferable one-year whole-home warranty, providing meaningful peace of mind. The nearly 2,300 SF lower level with 9' ceilings offers abundant storage and significant potential for future finishing, recreation, fitness, media or entertainment space. The 3-car attached garage with 12' ceilings provides exceptional storage and flexibility, including potential for vehicle lifts. Outside, professionally landscaped grounds feature mature trees, classic stone walls, sweeping lawns, garden areas, covered front porch/deck and inviting outdoor living spaces, creating a private New England retreat. Enjoy Redding's highly regarded schools, hiking trails, golf, tennis, paddle facilities, open space and quintessential New England character, with convenient access to Ridgefield, Wilton, Westchester and NYC. The property is also close to the Redding Country Club, Community Center, town green and local events and concerts. At $1,599,000, 2 Longwood Drive represents an exceptional opportunity to own substantial living space, private acreage and remarkable flexibility in one of Redding's most desirable locations. For buyers seeking a country estate with exceptional privacy, turnkey condition, premium finishes and convenient NYC access, this is a rare opportunity. Low inventory and this significant new price adjustment make this property particularly compelling. Schedule your private showing to fully appreciate the scale, setting and versatility of 2 Longwood Drive.