One of Salem‘s best examples of Federal-style architecture is the Pickman-Shreve-Little House at 27 Chestnut Street. It was constructed about 1819 by master builder Jabez Smith for Dudley L. Pickman. One of Salem’s wealthiest merchants, Pickman was a partner in the firm Devereux, Pickman & Silsbee and served as a state senator. The house was in his family until 1865 and was then owned, from 1872 to 1898, by Benjamin Shreve, a founder of the Boston jewelers Shreve, Crump, & Low, which is still in business. After Shreve‘s death, the house was then home to David Mason Little, a naval architect and photographer. He published a collection of his yacht photography in 1883 called Instantaneous Marine Studies. David M. Little also served as mayor of Salem in 1900 and was the last Collector of Customs at Salem, from 1903 until the office was abolished in 1913.

The house at 37 Chestnut Street in Salem was erected by master builder Jabez Smith in 1816-1817 for sea captain and merchant George Nichols. The house was also owned, from 1827 to 1845, by David Pingree and William A. Landers.

The facade of the Ireland-Emery House, at 131 Federal Street in Salem, does not face the street but instead fronts a yard on the west side. The house, which was built around 1797, is named for Jonathan Ireland, a blacksmith for whom it was erected, and Samuel Emery, a nautical instrument dealer and compass maker, active in Salem between 1809 and 1868, who acquired the house in 1828. The bay window above the front door is a later addition.