The first American settler was General Uriah Forrest, an aide-de-camp of George Washington. IN 1793, he built an estate on nearly 1,000 acres, original named "Pretty Prospects" and later renamed Rosedale. The estate served as home for the Youth For Understanding international student exchange organization for some time. In 2002, the Rosedale grounds were placed in a public conservancy and the farmhouse, said to be one of the oldest houses in the District, returned to residential use. Gardiner Greene Hubbard, first president of the National Geographic Society, built a colonial Georgian revival called "Twin Oaks" on 50 acres in 1888 as a summer home for his family. It is now site of the diplomatic mission of the Republic of China on Taiwan. Tregaron, present-day home of the Washington International School, is a Georgian house that was built in 1912.

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 (aka "Oak Hill" and "Red Top"). Cleveland lost re-election in 1888 and the estate was sold, with the Oak View subdivision subsequently platted in 1890. The Cleveland Heights subdivision was platted around the same time, and the Cleveland Park subdivision soon thereafter. Most of the houses built during this period were intended use as summer houses with wide porches, large windows, and long, overhanging eaves to combat seasonal heat.The extension of the Georgetown and Tennallytown electric streetcar line along Wisconsin Avenue generated development in Cleveland Park, but the real 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," similar to Chevy Chase, 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, Georgian Revival, and the Mission Revival.Later, simpler designs like Prairie style and Tudor Revival were popular.

Development was sporadic, affected by events such as the bankruptcy of the Cleveland Park Company in 1905 and the Great Depression. This resulted in a diverse collection of dwellings of different sizes, types and styles, often built next to one another. In the later 20th century, noted architects Winthrop Faulkner and I. M. Pei designed houses in the neighborhood.

Today's Cleveland Park offers a wonderfully diverse collection of architectural styles and home sizes of varying price points, along with some multifamily buildings and a growing retail center.