Kenwood, designed by the New York architect William Adams Delano, was built in 1939 as a weekend retreat for Major General and Mrs. Edwin M. Watson. In 1935 General Watson, a senior military aide and later secretary to President Franklin D. Roosevelt, chose the 78.5 acre site (land once owned by Thomas Jefferson and the site of Fancy Hill, the original eighteenth century estate house) while visiting the area as Roosevelt's representative to a Monticello graveside ceremony.
The most distinguished among Kenwood's many visitors was President Roosevelt, for whom the guest cottage – dubbed the "Little White House" by Life magazine – was built in 1940-41. Roosevelt, however, preferred the social activity of the main house to the privacy of the cottage, and on subsequent visits stayed in the bedroom nearest the entrance on the ground floor. The president made at least three more visits to Kenwood between 1941 and 1945, including four days in June 1944 while awaiting news of the Normandy invasion.
After General Watson's death in 1945, Kenwood was gradually transformed from a weekend retreat to a year-round residence by Mrs. Watson and her niece Miss Ellen Nash, who continued to occupy the cottage until her death in 1993. The bequest of Mrs. Watson left Kenwood to the University of Virginia, which in turn has granted a long-term lease to the Thomas Jefferson Foundation.