Located in the heart of Greenfield Hill at the top of Bronson Road, this iconic Connecticut estate sits on 2+ beautifully landscaped acres with distant water views of Long Island Sound. Across from a majestically developed family and horse-farm compound and outside the historic district, this home blends old-world charm with modern comforts. Originally built in 1844 and significantly expanded and renovated overtime, it features high ceilings, wide plank floors, intricate moldings, arched entries, and stunning natural light throughout. The home features a chef's kitchen and elegant entertaining spaces. Outdoors, enjoy a romantic keyhole-shaped gunite pool surrounded by published gardens, stone walls, mature plantings, and a vegetable garden with antique raspberry and blueberry bushes. A recently rebuilt carriage house with 2 bedrooms, 1.5 baths, kitchen, family room and art studio offers flexible space for a guest suite, pool house, home office, or in-law setup. Additional highlights include a cherry library, two brick chimneys, copper gutters, heated three-car cedar-lined garage, root cellar and chicken coop. This rare offering combines craftsmanship, privacy, and luxury-truly a Connecticut masterpiece in a premier Greenfield Hill location.