Located on a forty-acre parklike setting in a residential area, this outstanding Classical Revival brick building is one of the most elegant and impressive public high schools in Virginia. Believed to be the only privately endowed public school in the state, it was funded by a bequest in 1895 that Judge John Handley made to the City of Winchester. Constructed a quarter century later, the school is composed of a large two-story, hipped-roofed central block with a balustraded roof deck from which rises a three-stage wooden cupola. Centered on the east facade is a full-height, hexastyle pedimented portico with Corinthian columns, flanked by Ionic-columned loggias fronting both the central block and one-story brick wings. A wide brick terrace supported by a brick arcade below extends along the entire front of the building. The front entrance is reached at the top of a triple flight of stairs that rises from the grounds. The school is approached along a tree-lined divided boulevard that parallels the school's landscaped grounds of lawns dotted with trees.