89 John Perry Road

Welcome to the Benjamin Bosworth House, affectionately known locally as "The Castle." This extraordinary Federal-style home, Circa 1796, blends timeless craftsmanship with historic character. Set on 3 private acres, this 4,538 sq ft estate features 4 bedrooms, 2.5 baths, and 11 fireplaces across a thoughtfully designed layout. Notable architectural details include hand-carved mantels, doors, and windows-crafted by a woodworker who lived onsite through a winter. The centerpiece is a rare full-height monitor, originally a Masonic meeting hall, complete with fireplaces and built-in benches. Inside you'll find grand halls, a formal parlor, Dining room with bookcases & original China closet, tea room or keeping room gets afternoon sun, office, Studio, workshop, pantry, and laundry.1/2 bath with original wooden drain board & copper sink, Kitchen has antique basin, custom cherry wood pantry, hand painted stenciled floors. Primary Bed with private shower bathroom, 3 beds & office and full bath finish 2nd floor. Listed on the National Register of Historic Places, this one-of-a-kind home offers the charm of 18th-century design with the potential for modern customization. Own a piece of Connecticut history in peaceful Eastford. The house features a two-story main block topped by a hip roof, with a distinctive full-height monitor section projecting from the center. Benjamin Bosworth, for whom the house was built, was a significant figure in Eastford's history. He served on the building committee of the local Congregational Church and was instrumental in relocating the previous meeting house from the site. His desire for a distinctive residence led to the creation of this unique structure, which has since become a landmark in the area. Today, the Benjamin Bosworth House stands as a testament to early American architecture and the rich history of Eastford, Connecticut.