A refined Connecticut country residence for full-time living or weekend enjoyment, ideal for Westchester and NYC Buyers. Set on nearly three meticulously landscaped acres on a private cul-de-sac drive with only 4 residences, you will enjoy living in one of Redding's most desirable residential enclaves. 2 Longwood Drive offers a safe, secure, and sophisticated country lifestyle that resonates naturally with buyers seeking space, privacy, and enduring quality just beyond the city. Thoughtfully designed and meticulously maintained by its original owner, this custom-built colonial blends classic New England architecture with modern luxury, creating a residence equally suited for full-time living or refined weekend use. Spanning 6, 259 square feet, the home features beautifully proportioned interiors with spacious 9-14 foot ceilings, hardwood floors throughout, and an open yet elegant flow ideal for both everyday living and entertaining. A 47' stone-covered front porch, perfect for watching the amazing sunsets, and a central foyer introduce the main level, where light-filled spaces unfold seamlessly from room to room. The sunlit chef's kitchen serves as the centerpiece of the home, appointed with premium Sub-Zero/Wolf/Thermador appliances, custom cabinetry, a generous center island, and a butler's pantry, each designed for effortless hosting and daily comfort. The kitchen includes a hexagonal breakfast area with French doors overlooking the rear garden with a 100 foot stone wall., Enjoy time together in the spacious family room around the gas fireplace and pour cocktails at the wet bar, featuring a wine refrigerator and ice maker. Open the family room doors and relax outside on the 2nd stunning stone patio, all overlooking the serene, manicured grounds. A formal dining room offers elegant entertaining, while a dedicated home office with custom built-ins provides an ideal remote-work environment. An oversized mudroom with multiple points of entry connects the oversized 3-car garage (with a 12' ceiling to accommodate several lifts), 2nd front entry, and a rear patio adds the practicality expected in a well-designed country residence. The second level is anchored by a serene primary suite offering the rare luxury of two full bathrooms, complemented by three additional bedrooms, a large recreation room, and a thoughtfully placed laundry room. A dramatic third-level finished living space, served by a five-bedroom septic, functions beautifully as a fifth bedroom, in-law suite, guest suite, or private retreat, complete with a full bath and steam shower. An unfinished lower level of nearly 2, 300 square feet provides exceptional flexibility for future living, fitness, or entertainment space. Outdoor living is equally considered, with two stone patios surrounded by mature plantings, classic stone walls, and a huge sunny lawn space to add a pool. With a whole-house generator, and proximity to the Redding Country Club, town amenities, and commuting routes, 2 Longwood Drive presents a distinguished country residence defined by thoughtful scale, refined layout, and enduring quality, whether enjoyed full-time or on weekends. If you feel like getting outside, visit the nearby shops and restaurants in Ridgefield, Bethel, and Georgetown, or take-in the July 4th / Labor fireworks from one of the outdoor patios.