The Silver Hill Historic District, Weston, retains its integrity of location, design, setting, materials, workmanship, feeling, and association; and fulfills Criteria A and C of the National Register at the local level.Under Criterion A, the Silver Hill Historic District is important to Weston history as the location of the town’s first large-scale subdivision. The Weston Land Association was organized in 1905 to meet a growing need for middle class housing. To raise the money to purchase land, the association sold shares. Two curvilinear streets were laid out with regularly-spaced house lots.

Silver Hill was only the second, and by far the largest, Weston example of this relatively-new type of “suburban” planned development, sometimes referred to as a “garden suburb.” The fact that the Weston Land Association was a joint stock association funded by middle class entrepreneurs differs from other Weston subdivisions laid out by large estate owners. Early owners included skilled tradesmen and white collar workers.

Under Criterion C, the Silver Hill Historic District contains a diverse collection of architecturally notable houses set along one of Weston’s early scenic roads and within the early-20th century subdivision. The district is exclusively residential and includes Queen Anne and ColonialRevival houses ranging in date from 1892 to 1941, as well as 10 houses built after World War II.

Because houses have continued to be built within the Silver Hill Historic District up to the present day, the period of significance spans from 1892 (the date of the earliest house) to 1954 (the 50-year cut-off date).