The neighborhood acquired its name after 1886, when President Grover Cleveland purchased a stone farmhouse directly opposite Rosedale and remodeled it into a Queen Anne style summer estate called Oak View or Oak Hill (by other accounts, Red Top). When Cleveland lost his bid for re-election in 1888, the property was sold, and the Oak View subdivision was platted in 1890. The Cleveland Heights subdivision was platted around the same time, and the Cleveland Park subdivision soon thereafter. Early large-scale development was spurred by the neighborhood’s upland topography, which provided a breezy relief from the hot, fetid air in the lowlands that were then the built-up area of Washington, D.C. Most of the houses built during this period show their intended use as summer houses in the era before air conditioning, having such architectural features as wide porches, large windows, and long, overhanging eaves.
While the first subdivisions were made in response to the extension of the Georgetown and Tennallytown electric streetcar line along Wisconsin Avenue, the success of the neighborhood was the result of the Rock Creek Railway, built on Connecticut Avenue in 1892. Once Cleveland Park was connected to downtown Washington, the neighborhood’s second phase of development, as a “streetcar suburb”, began. The Cleveland Park Company oversaw construction on numerous plots starting in 1894. Most houses were designed by individual architects and builders, including Waddy B. Wood, resulting in an eclectic mix of the popular architectural styles of the time, notably the Queen Anne style (including the Shingle style), Georgian Revival, and the Mission Revival. In later years, simpler schools of design such as the Prairie style and Tudor Revival came to dominate.