Deanwood began as farmland, much of it maintained by enslaved African Americans. After the Civil War, African Americans came to predominate in this middle- and working-class area, though the neighborhood remained mixed until the 1930s. An array of architects, including W. Sidney Pittman and Howard D. Woodson, and numerous skilled local craftsmen designed and built most of Deanwood's housing in this new suburb before World War II. Eminent educator Nannie Helen Burroughs chose this area for her influential boarding school. Today many areas, especially along Sheriff Road, retain an unusual small-town character.