The area we now call Cleveland Park in Washington D.C. was once a part of a massive 1000 acre estate owned by Colonel Ninian Biell. He called his estate Pretty Prospect and built a small stone cottage on the land in 1740. In 1790, the property was acquired by General Uriah Forrest, who would later become mayor of Georgetown, and a large wood-framed house was built onto the front of the stone cottage. Forrest renamed the property Rosedale. When his son inherited this land, he built an even bigger home and called it Forrest Hill. In 1886, Forrest Hill was purchased as a country retreat by then-president Grover Cleveland who converted the house into a Victorian mansion and renamed it Oak View. It is from President Cleveland that the current neighborhood takes its name.
After Cleveland lost his reelection bid in 1889, the land was purchased and converted into housing subdivisions. The neighborhood’s early success was made possible by the Rock Creek Railway line which ran up Connecticut Avenue from downtown all the way to Chevy Chase Lake in Montgomery County, Maryland. In order to make this streetcar line happen, a massive bridge had to be built over the Klingle Valley and Rock Creek connecting the area to the rest of the city. The neighborhood developed around the natural contours of the land, with a little help from the firm of landscape architect Frederick Law Olmstead, and you’ll find more winding roads here than in most parts of the city. Many of the houses were built to be unique to those around them and many were designed by renowned architects of the day. The result was that Cleveland Park was once heralded as the “prettiest suburb of Washington”, and many of those beautiful houses survive in the neighborhood today.