Census-designated places (counted in New York as Hamlets) in the school district, of which Roosevelt is the sole comprehensive high school, include Haviland, Hyde Park, Marist College, Salt Point, and Staatsburg.

Construction began in 1938 and was one of three schools erected as a Depression-era Public Works Administration project in Hyde Park.

[3] It was originally called the Franklin Delano Roosevelt Junior-Senior High School and may be the only public high school in the United States built under the auspices of, and named for, a sitting president.

As enrollment increased, the town began construction on the current high school building which opened in 1965.

The original building was listed on the National Register of Historic Places in 2011.