In the early 1920’s the School Board leased Old Stone Presbyterian Church on Piccadilly Street to house classes for the black children of Winchester. The original Frederick Douglass School, containing eight classrooms, was erected in 1925. The construction costs of $28,000 were funded by the Handley Board of Trustees.
From 1925 to 1951 Douglass housed students in grades six through eight. With the addition of a library, a gymnasium, a science room, and a shop, Douglass became a 12-grade school with an enrollment of approximately 350 students. Four more classrooms were added in 1963-64 at a cost of $70,000, and the school, renamed Winchester Intermediate School, housed some sixth grade and all seventh grade students in the city. During the summer of 1974, the school was remodeled at a cost of $98,000 and renamed Frederick Douglass Elementary School. Until June 1990 students in kindergarten through fifth grade comprised the school population.
Construction of a new elementary school was begun in March 1989 as the first phase of the Winchester City Schools Capital Improvement Program. Built at a cost of $6,000,000, the school was constructed in the southern end of Winchester to accommodate the city’s recent growth. In May 1990 the School Board voted to transfer the Frederick Douglass name to the new building. The new Frederick Douglass Elementary School received students for the first time on September 4, 1990. Since that time William Askew, John Penney, Ruth Ann Martin, and Nancy Lee have been principals. The current principal is Stephanie Downey.