The main building of the high school was built in 1969, four years after the three suburbs of Green Tree, Dormont and Castle Shannon combined their students to form a common school district. The high school was built on a tract of land in neighboring Mount Lebanon, just outside the southwest border of Dormont. The site adjoined the Kelton Avenue Elementary School, which no longer exists. The name 'Keystone Oaks' refers to the merger of the three school districts: 'key' for the 'door' in Dormont; 'stone' from the 'castle' in Castle Shannon; and 'oak' as a tree in Green Tree. The name was suggested by Thomas Clark, of the Class of 1965, and was chosen as part of a student competition to name the new school district. Due to the deteriorating state of the district's Jay Neff Middle School, a new middle school was attached to the old high school in 1996. This precipitated a massive redesign of the grounds, including the demolition of a little-used outdoor amphitheatre and the construction of a band practice field and new tennis courts. These tennis courts were later repaved in 2006. Through the summer of 2001 and the 2001/2002 school year, the high school was renovated.
Academic achievement
In 2013, Keystone Oaks was featured in U.S. News & World Report's America's Best High Schools edition. The Washington, D.C.-based American Institutes for Research study included Keystone Oaks among the top 10 percent of all public and private high schools nationally and in Pennsylvania. The report also rated Keystone Oaks the ninth best public or private high school in Allegheny County. In 2009, Keystone Oaks High School was ranked 83rd out of 123 western Pennsylvania high schools, by the Pittsburgh Business Times for academic achievement based on three years of the PSSAs on: reading, writing, math and one year of science. College remediation According to a Pennsylvania Department of Education study released in January 2009, 41% of Keystone Oaks School District graduates required remediation in mathematics and or reading before they were prepared to take college level courses in the Pennsylvania State System of Higher Education or community colleges. Less than 66% of Pennsylvania high school graduates, who enroll in a four-year college in Pennsylvania, will earn a bachelor's degree within six years. Among Pennsylvania high school graduates pursuing an associate degree, only one in three graduate in three years. Per the Pennsylvania Department of Education, one in three recent high school graduates who attend Pennsylvania's public universities and community colleges takes at least one remedial course in math, reading or English.
The high school offers a Dual Enrollment program. This state program permits high school students to take courses, at local higher education institutions, to earn college credits. Students remain enrolled at their high school. The courses count towards high school graduation requirements and towards earning a college degree. The students continue to have full access to activities and programs at their high school. The college credits are offered at a deeply discounted rate. The state offers a small grant to assist students in costs for tuition, fees and books. Under the Pennsylvania Transfer and Articulation Agreement, many Pennsylvania colleges and universities accept these credits for students who transfer to their institutions. For the 2009-10 funding year, the school district received a state grant of $9,415 for the program.
Extracurriculars
By Pennsylvania law, all K-12 students in the district, including those who attend a private nonpublic school, cyber charter school, charter school and those homeschooled, are eligible to participate in the extracurricular programs including all athletics. They must meet the same eligibility rules as the students enrolled in the district's schools.
