Situated towards the center of a gently sloping six-acre site, the Daine House was originally a one-story, flat-roofed structure with a rectangular footprint, a partial basement, a wide porch, and a detached two-car garage connected to the main house by a pergola. The house was clad in vertical wood siding and the roof was clad in wood shakes. Two additions--a two-story addition at the back corner of the house and a small entry vestibule--have only slightly altered the original appearance of the Daine House.
Using a palette of traditional New England building materials, architect Victor Christ-Janer designed this modest house to blend into the surrounding landscape, but its flat roofs, floor-to-ceiling fixed plate glass sash (looking out on the porch), and an open plan mark the house as clearly Modern.
In June 1953, Robert Roles, a well-known developer and contractor in New Canaan, bought four acres of land on the west side of Briscoe Road from Richard and Wynne Bolton. By September 1953, a house designed by architect Victor Christ-Janer was under construction on the site. Roles and Christ-Janer worked together on several speculative house projects in New Canaan. In the spring of the following year, Isabelle Daine purchased the property from Roles. In 1959, Daine sold the property to Horton Heath, who bought two additional acres for the site in 1962. Heath added two outbuildings to the property: a playhouse (c. 1960) and a stable (c. 1963). In 1963, the Heath family remodeled the original house and built a discreet two-story addition at the back corner of the structure. In 1968, a concrete swimming pool was built. By 1976, Nadine and James Sweeney, Jr., owned the property. At the time of the survey, the property was still held in the Sweeney family.