One of the most impressive Colonial Revival-style schools in the Shenandoah Valley, Robert E. Lee High School is located on five acres atop a hill overlooking an important crossroads in the City of Staunton. Designed by the local firm of T. J. Collins and Sons in association with St. Louis-based architect and notable authority on the design and planning of schools William Butts Ittner, the high school was built in 1926 as an enduring testament to the importance of education in Staunton and was the city’s first separate school for secondary education. The noble detailing, careful proportioning, and prominent siting of the building were intended to inspire both students and passersby. Most of the exterior of the building and much of the interior have remained unaltered since it was built, a tribute to the lasting elegance of the structure. The school’s period of significance begins in 1926 and ends in 1954, with the addition of the flanking wings. Robert E. Lee School closed for public education in 1983, and was later converted for use as apartments under the name Gypsy Hill Place.