Nestled in a peaceful wooded setting, this beautifully maintained 4-bedroom, 2.5-bath colonial offers comfort, privacy, and modern updates throughout. Set on 2.57 secluded acres with an additional 3+ acres of bordering open space, this home provides ideal escape while still being minutes from town amenities and major commuting routes. Main level features an inviting layout with an eat-in kitchen, a formal dining room with a wood-burning fireplace, a spacious living room, a large sunken entertaining area with vaulted ceiling and radiant heated floors, and a dedicated home office perfect for remote work. Upstairs are four well-sized bedrooms with refreshed carpeting (2024). Extensive updates include a new roof and skylight (2024), new furnace and oil burner with a 10-year transferable warranty (2024), new Anderson sliding doors to deck (2024), new gutter guards (2024), and a new well tank (2023). Interior and exterior, including deck, were freshly painted in 2024-2025, creating a move-in ready home with nothing left to do. Outside, enjoy a stone driveway, a freshly painted deck for outdoor entertaining, and wooded surroundings that provide peace and privacy year-round. Located in highly regarded Newtown Public School District and convenient to Fairfield Metro for an easy New York City commute, 59 Great Ring Road combines timeless charm, thoughtful upgrades, and best of Connecticut living.