Ebenezer Clark constructed the house about 1725, possibly as early as 1684, and sold it to John Humphreville upon his marriage to Rebecca Clark in 1730. The house construction was a two-over-two post-medieval post and beam structure with a summer beam for added support. Descendants of Ebenezer owned the house until 1788 when it was purchased by sea captain Thomas Ward and his family. After the Captain's death in 1839, the Wards lived in the house until they sold it to Susan Perrin in 1861.
During this time, a shed was built across the back of the house, giving it the traditional saltbox shape. A large cooking hearth dominated the new addition. Also at this time, the two original first floor rooms were remodeled in the Georgian style. Various members of the Ward family lived in the house until it was purchased from Henrietta Heitmann by Charles Elliott Pickett in 1909. Mr. Pickett added the sunroom/library to the west side of the house. In 1865 William Wallace Ward and Israel K. Ward were among the founders of the New Haven and West Haven Horse Rail Road Company which ran a horse drawn trolley between Elm Street in West Haven and New Haven. In 1894 it was consolidated with the Winchester Avenue Railroad Company, by which it became known. In 1868 Louisa Ward Heitmann purchased the house and in 1897 ownership passed to her daughter Henrietta, a businesswoman. Henrietta Heitmann added a wing to the house,which she used as a dame school. She also raised the shed to a full two stories and added a porch to the front of the house. Henrietta Heitmann was involved in several other business enterprises, including the schooner Charles F. Tuttle.
In the 20th century, the house was occupied by several families in succession. In 1919, Marie and Philandro Armstrong may have covered the clapboards with shingles. In 1922 Marie Gouin Armstrong opened an antique shop called “The Stepping Stone,” In 1936, the Dwight Hamilton family rented the house from new owner, George E. Hodson and opened a tearoom, the Hamilton House . During the 1940s, the house was owned by the Fennessy family. In those years, the hearth room was remodeled as a “colonial restoration.”
Dr. and Mrs. Nicola Milano owned the house from 1949 to 1995. During this period, the house was modernized with upgraded electricity, additional bathrooms and a modern kitchen. However, the basic structure of the house was left intact.