Platteville's founder John H. Rountree originally owned all the land associated with the Bayley Avenue Historic District. Rountree's Greek Revival style house, located at 150 Rountree Avenue, was completed in 1853 and is the oldest building in the District. Both this house and all the surrounding land remained in Rountree's possession until his death in 1890. His heirs then platted it as the Homestead Addition; because it was located just to the south of Platteville's downtown commercial district, lots sold quickly. Within five years, almost half of the houses that make up the Bayley Avenue Historic District had been built, most of them located in the north half of the District closest to the downtown. More houses were built between 1896 and 1909, years during which the revitalization of the local mining industry greatly increased Platteville's population. By 1916, all but three of the District's buildings had been completed.

Nearly half of the district's houses are examples of the Queen Anne style. Built between 1890 and 1909, they tend to sit on the larger lots on the high ground at the two ends of the District. One of the District's most impressive houses is the W. N. Smith House, built at 155 Bayley Avenue in 1915-16 for the owner of Platteville's Vinegar Hill Mining Co. The Chicago firm of Miller, Fullenwider & Dowling designed this brick and stucco Craftsman Style house. The firm also designed Platteville's Craftsman Style Carnegie Library at 190 Market Street.

The houses in this district are private residences. Please respect the rights and privacy of the residents.