Massengale has won awards for architecture, urban design, historic preservation and architectural history. New York 1900 was the first architecture history book nominated for a National Book Award. In 1992, Massengale won the first Progressive Architecture New Public Realm award with a Subway Suburb in the South Bronx, and a year later a house he designed won prizes from 3 chapters of the AIA and Hudson Valley. After serving as Seaside Town Architect in 1986, he was awarded a Seaside 20th Anniversary Medal.