 The district contains more than thirty structures built before 1750, many of which retain First Period and Georgian styling.Some of the more interesting houses include that of John Caldwell, built c. 1660 on the site of Governor Simon Bradstreet's original 1630s house, the c. 1770s town jail, which was converted into a Greek Revival house in the 19th century, and the c. 1727 house of Reverend Nathaniel Rogers.One of the more unusual later buildings included on the district is a Stick Victorian at 12 High Street.