William Mills and Daniel Hyde, two carpenters who lived in the houses, likely designed and built the Greek Revival double residence. After the Lynn Historical Society acquired the house in 1913, John Chandler Fowler replaced the double entrances with a single doorway and remodeled the rear ell. Only the two unusual tripartite windows above the Doric portico remain on the exterior to suggest a double house. In 1929 the historical society hired William T. Aldrich to construct the large brick fireproof structure in the rear to house their collections. They also moved a small “ten-footer” shoe shop to the property to commemorate the industry most responsible for Lynn's development. This modest structure is typical of a shoemaker's shop before industrialization.

Near the historical society property, another local carpenter, Frederick Todd, built a small house, evidently inspired by the published designs of Andrew Jackson Downing. The modest size and proportions of the ToddDame Cottage, with its central gable roof pavilion, are characteristic of several designs published in Downing's books. Also typical are the ornamental details, such as the simple brackets under the overhanging eaves and ogee-shaped veranda brackets. The entrance consists of a round arched door and hood molding, while the entire principal facade has flush board siding.