[1] The core of the Nathaniel Parsons House, 58 Bridge Street, was built c. 1719,[3] and still exhibits characteristics of First Period construction.

[2] The Shepherd House, 66 Bridge Street, was built in 1795, and remains a fine example of Federalist architecture with later stylistic modifications.

[2] The Isaac Damon House, 46 Bridge Street, was built c. 1813, and its main block is a typical five-bay two story Federalist.

These three houses stand near the junction of Main and Bridge Street, on some of the earliest plots laid out.

The Damon House was built by Isaac Damon, one of the area's most important proponents of the Federal style of architecture; his influence, and that of Asher Benjamin, had a major influence on the architecture of the area and the time.