Simeon P. Smith's house at 154 High Street dates to 1810, its central doorway framed by pilasters under a triangular pediment. It is one of a modest number of such houses to survive the devastating fire of 1813, and it was listed on the National Register of Historic Places on November 14, 1972. The building rises two-and-a-half stories in a wood-frame with a gabled roof and interior chimneys; brick chimneys sit on either side of that roof.
Look at the central doorway framed by pilasters, topped by a triangular pediment above a four-light transom, and set among windows with delicate Federal-period moulding. A secondary entrance has been added to one side, and inside you would find Federal-style cornices and a fine carved arch in the central hall. Many rooms retain original Federal-period styling, while some were altered by subsequent owners to simpler Greek Revival elements.
Notice this house facing High Street on the Hill's northeastern edge, part of the cluster gathered here south of Deer and High streets.