This is among the finest of Chestertown’s many mid- to late-eighteenth-century Georgian houses. The substantial five-bay house with partial-hipped roof was built for merchant Samuel Massey. Before it was finished, however, it was sold in 1749 to attorney and businessman Thomas Ringgold IV and his wife, Anna Maria. They added the banked rear wing that included a basement kitchen with huge cooking fireplace, cellars, and vaults. In 1772 it passed to their son Thomas Ringgold V, who operated his dry goods store and “computing house” for the neighboring customs collector from here, along with a waterfront wharf and storehouses. The house remained in the family until 1794. Following subsequent owners, Wilbur Ross Hubbard restored the house in 1975, and after his death it was transferred to Washington College, where it now houses the C. V. Starr Center for the Study of the American Experience.