The Chesterfield Heights Historic District was initially laid out in 1904 by the Chesterfield Syndicate Corporation as an elite residential suburb in the city of Norfolk. The neighborhood was advertised with extensive amenities, attractive lot sizes, and strict building requirements. Initially aimed at upper-class residents, Chesterfield Heights was forced to reduce lot sizes during the years of World War I as competition among suburban neighborhoods grew; thus Chesterfield Heights began attracting more middle-income residents. The community contains homes in a range of styles, the earliest being imposing Queen Anne and Revival styles with extensive ornamentation, to the modest Craftsman-style bungalows appearing after 1914. Currently encompassing the neighboring historically separate community of Riverside, the Chesterfield Heights Historic District tells the story of suburban development in Norfolk during the early years of the 20th century.