Brookeville Academy, founded in 1808 largely by Anglicans, won acclaim as an academic and character-building institution for a century. Students came from as far as Baltimore, Washington, and Frederick. First a boys' school, then co-ed, the Academy decreed that "discipline...will be mild but firm. Pupils who, by indolence, vicious language or conduct, or by pointed opposition to authority, injure their companions, or diminish the usefulness of the institution, will not be permitted to remain..." In more recent times the building was used as an American Legion hall and election polling place.

Massive Marywood , c.1796, housed the Brookeville Academy from 1869 to 1909. It then served as a public high school until 1917. The home stands on a historic tract known as Bordley's Choice-1,000 acres purchased by John Riggs in 1751 just north of Brookeville. His four sons came onto the land in the 1760s and established the influential Riggs family on Sandy Spring's northern fringe. Tragedy struck Marywood in 1917, when 30 guests at a Silver Tea collapsed a rickety porch, fatally injuring Ella Lansdale Hartshorne.