Rare opportunity & entertainer's private dream! Welcome to a timeless estate in 1 of Greater Waterbury's sought-after neighborhoods, backing onto the The Country Club of Waterbury. This 5-bed, 3.5-bath historic colonial spans 3,440 sqft. & blends character w/ modern comfort, 2 fireplaces & 2 primary suites. Set on over 4 ACRES of secluded, park-like grounds, surrounded by trees, stone walls, rolling lawns.. a sense of retreat! Property offers an in-ground pool, tennis court, pool house, expansive stone patios, & a covered slate terrace, perfect for gatherings or quiet moments alike. Inside, classic brick charm opens to a gracious foyer with hrdwd flrs, arched doorways, & custom millwork. The chef's kitchen offers bespoke cabinetry, granite breakfast bar, stainless GE Monogram appliances, gas oven, flowing seamlessly into the dining area w/ terrace access. For entertaining, enjoy the classic library/office w/ custom built-ins & fireplace, or the spacious living room w/ 2nd fireplace opening to a sun-3-season glass veranda. Upstairs, 2 primary suites: 1 w/ a remodeled bath w/ a wk-in shower, the other has its own private powder room. Bedrms offer space & gleaming hrdwd flrs. Central air & natural gas heat. Setting is Private/ serene, estate surrounded by oaks/evergreens, gardens & seclusion. Enjoy a pool w/ a patio & kitchenette, pool house, great yard & tennis courts for endless recreation. History of hosting distinguished guests, a landmark home ready for its next chapter!