De Gerenday was brought to America at the age of eight months by his parents; his father was a minister and author, and his mother was an opera singer and music teacher. He studied at the Butler Institute in Youngstown, Ohio; South Dakota State School of Mines; Ursinus College in Collegeville, Pennsylvania; the University of Shrivenham, England; the Academy school; and at the Beaux-Arts Institute of Design, New York. Among his teachers were Charles Hinton, Leon Kroll and Arthur Covey; he also served an apprenticeship with the sculptor Alexander Finta. He married, first, Mary E. Lord and, following her death in 1976, he married Elisabeth Gordon Chandler in 1979.
De Gerenday is a specialist in relief carving. Among the medals of his design are the Gold Medal of the Society of Electrical Engineers and the bronze Admiral Farragut medal of the New York University Hall of Fame. In coinage, he has designed the Battle of the Alamo and the Centennial of Professional Baseball silver coins, both for the National Commemorative Society. His larger works include reliefs for the court house in Aberdeen, South Dakota; an equestrian relief portrait of Lt. Junot for the Museum of Algiers, Algeria; and portraits of Dr. Otto Klitgord, P. H. Batten, and Jacques Lipchitz.
He is a member of the National Sculpture Society, the Allied Artists of America, and the National Arts Club, among others. His many awards include the Academy's Speyer Prize which he won in 1947, and again in 1962. De Gerenday first served on the Academy Council from 1945 to 1948, and was returned to it when he was elected its recording secretary in 1957 and 1958.