Wauwatosa was established in 1835 as Hart's Mills; it was renamed in 1842, shortly after the town of the same name was established. Among the early settlers to the area was Oliver Damon, who built a small home along the west side of present-day Wauwatosa Avenue. The roadway developed along a section line and led nearly directly into the heart of the village. Although settlement along the roadway was sparse between the 1840s and 1880, development grew in the 1880s as a number of subdivisions were created from the larger farmstead parcels.

Between 1885 and 1900, the roadway truly began to develop its identifiable residential character. Specifically, the street was graded and graveled in 1898 and sidewalks were installed around the turn of the century. It was not, however, until 1919, when the street was paved with concrete. By the late 1920s, all of the lots along the Avenue had been purchased and improved, resulting in the residential, tree-lined street that is still seen today.

Because of the district's nearly 80 span, its homes comprise a distinct and dense collection of high-style architecture that was popular between the 1840s and 1920s. Styles include Greek Revival, Italianate, Queen Anne, English and American Arts and Crafts and Craftsman, Georgian and Colonial Revival, as well as Italian Renaissance and Mission/Spanish Colonial Revival, with a minimum of vernacular examples. Also found within the district are three designs directly identified to published catalog or magazine plans by Gordon Van Tine, the Architects' Small House Service Bureau, as well as renowned Arts & Crafts proponent Gustav Stickley. While some modern materials have replaced the originals, the vast majority of the homes retain a very high level of historic integrity.

The houses in this district are private residences, please respect the privacy of the owners.