A refined Connecticut country residence for full-time living or weekend enjoyment, ideal for Westchester and NYC Buyers. Set on nearly three private, landscaped acres in one of Redding's most desirable residential enclaves, 2 Longwood Drive offers a 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 9-foot ceilings, hardwood floors throughout, and an open yet elegant flow ideal for both everyday living and entertaining. A stone-covered entry and 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, and Thermador appliances, custom cabinetry, a generous center island, and a butler's pantry, all designed for effortless hosting and daily comfort. 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 French doors and relax outside on the 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 connecting the garage, 2nd front entry, and 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, 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 ample space to add a pool. With a three-car garage, 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.