In 1891, Highland Springs school was a one-room frame building with five pupils and a teacher. By 1905, Highland Springs had grown to about 25 students, ranging in age from seven to 16. By 1907, the community had outgrown the one-room school and replaced the building with a four-room building on the lot immediately east of the present school. It wasn’t long before an eight-room addition was needed. The current high school, located in Henrico County's Varina District, opened in 1952, and annexes were added in 1956 and 1957. During the 1970-71 school year, a massive building program began with a two story addition to the existing building. This new addition connected the two annexes with the main building.

In 2019, construction began adjacent to the school on a replacement for the 1952 building. A new two-story, 265,000-square-foot Highland Springs High School opened for the 2021-22 school year. The 1952 building was repurposed as the Oak Avenue Complex — a community hub and home to An Achievable Dream Certified Academy Secondary.