Discover exceptional living at this distinguished 5-bedroom, 3-bathroom ranch home spanning over 5,000 square feet on prestigious Whippoorwill Lane in coveted Weston. Built in 1955 and situated on a magnificent 1.72-acre lot, this timeless residence offers the perfect blend of classic New England charm and modern potential in one of the most sought-after communities. Ready for a new homeowners personal touch and contemporary updates, this well-maintained home presents an ideal opportunity to add modern finishes while preserving its inherent character and charm. The thoughtful layout includes private quarters perfect for in-laws or an au-pair providing flexibility for multi-generational living. The property's prime location provides both tranquil privacy and convenient access to Georgetown's charming restaurants and shops, Route 7 amenities, and the natural beauty of nearby Devil's Den Preserve, while families benefit from Weston's A+ school system. With generous, well-proportioned living spaces ideal for both family life and entertaining, plus a pool and expansive grounds offering endless possibilities for customization and enhancement, this rare opportunity on Whippoorwill Lane represents the epitome of sophisticated CT living where bucolic serenity meets modern convenience.