Welcome to 50 Kevinwood Drive in Caledon Village, a rare chance to own a beautifully upgraded family home on nearly half an acre with no homes behind and stunning sunset views. With approximately 2,600 sq ft above grade and approx 4,000 sq ft of finished living space, this property combines comfort, style, and functionality with over 4,700 sq ft total useable space. The main floor boasts a gourmet kitchen, completely redone in 2022 with quartz counters and backsplash, farmhouse sink, moveable island, under-counter lighting, gas stove, and motorized garbage cupboard. From the Breakfast area, walk out to a massive deck (stained 2025) overlooking a private, landscaped backyard. Separate living & dining area plus a cozy family room with gas fireplace (2017). Elegant touches include 7-inch baseboards on the main floor, 6-inch on the second, and a new circular staircase with railings (2022).Upstairs find 4 generous bedrooms and 2 updated bathrooms (2015). The primary suite features a 4-piece ensuite, 2 closets with built-ins, and space for a sitting area. The finished walkout basement adds versatility with an exercise room, separate entrance, 2 bedrooms, a kitchen, and a 3-pc bath perfect for extended family, guests, or rental potential. Meticulously maintained! Roof shingles (2022), furnace and AC (2015), 200-amp service (ESA inspected 2009), and a heated, insulated garage (2022) with 220V outlet ready for adding EV charging. Garage doors replaced in 2015, driveway repaved in 2019 and resealed in 2025. Outdoor spaces are equally impressive, with landscaping completed in 2010 and 2020, creating a private oasis with plenty of room for entertaining. Smart touches like Alexa voice command for main floor lighting complete the package. Blending modern updates with timeless charm, this exceptional property offers space, privacy, and tranquility, just minutes from amenities and commuter routes. Don't miss your chance to make 50 Kevinwood Drive your forever home!