Well known for his Long Island estates of the 1910s and 1920s and public work in Washington, D.C., designed in partnership with Chester Holmes Aldrich, Delano designed several country houses in Virginia and the Charlottesville area. Kenwood, for General and Mrs. Edwin Watson, is the most accessible of these and has some historical significance as well, since General Watson was Franklin D. Roosevelt's military attaché, and, from 1940 onward, his secretary. President Roosevelt visited the house during World War II. Delano's preference for English classical forms is well demonstrated. An interesting variation on the traditional plan is the entrance through what is essentially the service wing into a long hall that terminates in a double cube sitting room–music salon designed to display a set of antique Belgian tapestries and containing original furnishings. The music salon overlooks the boxwood garden. The other public spaces are to either side.

The cornerstone was laid in 2000 for a 15,000-square-foot research library building (Hartman-Cox of Washington, D.C.) sited adjacent to the house and designed to harmonize with it.