Dole-Little House was built around 1715 with materials salvaged from an earlier structure. Its first owner was Richard Dole, a cattleman, who built a two-room, central-chimney house with a small kitchen shed at the rear. This shed has since been replaced with a larger lean-to. Decorative carpentry and finishes include chamfered edges, molded sheathing (especially in the hall and parlor), and possibly original stair balusters.
Acquired by Florence Evans Bushee in 1954, the house was subject to an extensive restoration. Workers discovered that new mortise and tenon joints and various other changes had been made to many of the salvaged framing members to allow them to conform to the plan of the "new" house.
During restoration efforts, the lean-to was rebuilt with new timbers, and sash windows from the front of the house were reinstalled in the lean-to. Decorative paneling from one of the chambers was removed and reinstalled in the National Museum of History and Technology in Washington, D.C., while a reproduction of the paneling was installed in the chamber at Dole-Little House. Historic New England received the title to the house after Mrs. Bushee's death in 1975.