Picture Gov. John Wentworth's elegant Georgian residence, built in 1763 for Portsmouth's leading political and economic circles. Built in 1763, this house is celebrated for its fine Georgian finishes and for its long associations with leading political and economic figures of 18th- and 19th-century Portsmouth.
The house was listed on the National Register of Historic Places in 1973, and since the early 20th century it has been part of a senior care complex. You’re on the south side of Pleasant Street at Wentworth Street; the house faces north toward the street and stretches southward toward the South Mill Pond where a large modern addition now houses the bulk of the care facilities. Take in the building’s 2½ stories under a hip roof, its clapboarded exterior, and the wooden quoins at the corners.
The cornice is lined with modillion blocks, and the main facade is a perfectly symmetrical five bays wide. At the center, the entrance is topped by a half-round transom window and sheltered by a Federal-period portico with a modillioned cornice, a hip roof, and a low surrounding balustrade. Notice the modillioned cornice and transom doorway, then picture the addition reaching south toward the pond.