It is located at 38°56′11″N 77°3′58″W / 38.93639°N 77.06611°W / 38.93639; -77.06611 and bounded approximately by Rock Creek Park to the east, Wisconsin and Idaho Avenues to the west, Klingle and Woodley Roads to the south, and Rodman and Tilden Streets to the north.

[4] The first known settler was General Uriah Forrest, an aide-de-camp of George Washington who built an estate called Rosedale (now at 3501 Newark Street) in 1793, when he began serving as a Congressman from Maryland.

Gardiner Greene Hubbard, first president of the National Geographic Society, built the colonial Georgian revival Twin Oaks on 50 acres (200,000 m²) in 1888.

The neighborhood acquired its name after 1886, when President Grover Cleveland purchased a stone farmhouse opposite Rosedale and remodeled it into a Queen Anne style summer estate called Oak View or Oak Hill (by other accounts, Red Top).

[6]: 4 [7] Red Top in the meantime was inhabited by Washington architect Robert I. Fleming and later by his widow, and eventually demolished in 1927 to be replaced on the same site by the neo-Georgian mansion that still stands at 3536 Newark Street NW.

[8] 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.

[6]: 2  Once Cleveland Park was connected to downtown Washington, the neighborhood's second phase of development, as a "streetcar suburb", began.

Development proceeded in fits and starts, punctuated by such events as the bankruptcy of the Cleveland Park Company in 1905[6]: 9  and the Great Depression in the 1930s.

It was anchored by Piggly Wiggly and built in an L shape with dedicated parking space for shoppers in the front, a novelty at the time.

The Cleveland Park Club was founded in 1922 to "promote social intercourse, recreation and sports, literature and the arts, and for mutual improvement" of the neighborhood in the days before television and widespread broadcasting and movies.