Kennedy was from Kansas and married Alberta "Abbie" May Francis (Kennedy) and they had a son, George Milton Kennedy (1904 – 1979), but Abbie died in 1913. Roy and George moved to Oakland, and Roy married Violet Stut (Kennedy) (September 30, 1884 – February 2, 1970) on November 24, 1915. The 1920 census lists Roy's profession as wholesale meat salesman; the 1924 directory lists Roy and George as contractors; by 1930 Roy's profession was real estate salesman.
The Kennedys lived in the house and office on Foothill from at least 1920 to 1942. In 1940 George was living there with his wife Margaret Critchlow (Kennedy), their son Jack Lawrence Kennedy, and Margaret's mother Blanie Critchlow. From c.1928 George was working as a fireman for the fire department in Alameda, where they lived for a time.
Roy died in 1953 and Violet in 1970, and they are buried in Evergreen Cemetery.