The Oak Hill Historic District is an early-to-mid 20th century residential neighborhood. Historically, the district is associated with a period, 1900-1941, in which Hagerstown experienced industrial and population growths unprecedented in the city's history. The district is also important for its association with persons significant in local history. Oak Hill was home to many, if not to most, of the city's industrial, commercial, social and cultural leaders of this period. The Oak Hill addition to Hagerstown was laid out in 1909 for Mrs. Clara Hamilton, the widow of William T. Hamilton, Governor of Maryland (1880-1884). The properties were sold by the Hamiltons with covenants in the deeds affecting type, use, cost, siting and settings of buildings. Only residential structures were allowed. The minimum cost of a house was designated at $2,500. Objectionable and unsightly outbuildings were forbidden. Mrs. Hamilton also retained rights to the trees lining the streets.

Architecturally, the houses in the district represent examples of the major architectural styles popular for residential construction in the first third of the 20th century. The houses are generally Colonial or Georgian Revival in stylistic influences although excellent examples of Spanish and Tudor Revival, Foursquare, Queen Anne, Dutch Colonial Revival, and Arts and Crafts Bungalow are present. The buildings include some of the finest examples of these styles found in Hagerstown and collectively exhibit a range of architectural expression, craftsmanship and technique of the period. From the point of community planning, the Oak Hill area is important as the first and only significant section of Hagerstown to be developed along the lines of the garden city movement that began in the country in the mid 19th century. The district is characterized by large lots, open spaces, deep set-backs, curving streets and tree-lined boulevards.