The first Round Hill School was built in 1786 and was located on land lying in Blagg's Clove, bounded on the south by Blagg's Clove Road and on the other two sides by two roads, one from Coleman's Mill the other from Blooming Grove into Blagg's Clove. This is now the intersection of Round Hill and Helms Hill Roads. Jonathan Tuthill, who had come to Orange County from Long Island in 1735, gave land for the original school. Sunday school was also held in the schoolhouse. Books used at that time included Thompson's Arithmetic and Brown's Speller and Reader.

The second Round Hill School was built in 1864 on the same site by James Wite, who left immediately after completing the job to fight in the Civil War. The original school was torn down and many of the stones and timbers were used to enlarge the new building. The new schoolhouse was described as a "stone building shaded by ancient and noble trees on a half-acre triangular plot at the foot of Round Hill and the junction of country roads. The growth of myrtle that adorned the area then is still evident today.

In cold weather, the one and only teacher was expected to stoke the coal stove that provided heat for the one room schoolhouse. Around the coal stove sat twenty to twenty-five children ranging in ages from five to nineteen, on benches holding approximately four students. Subjects taught to the children included arithmetic, reading, geography, local and American history, and Palmer penmanship. Physical education was composed of doing knee bends and other strenuous exercises. Many of the young boys left the schoolhouse in May to help their fathers raise sheep, tend to the fields, and farm.

By 1933, area schools had become centralized and use of the Round Hill School came to an end. Blooming Grove children attended school in Washingtonville and the old one room school sat idle. Today, the one room schoolhouse remains a private home; however, through three decades of growth and development the Round Hill School continues to flourish with students eager to learn! With "Elementary" added to the school's moniker, the third rendition of the Round Hill School opened in 1968 at the intersection of Route 208 and Round Hill Road. Today the Round Hill Elementary School serves as a testament to the strength and growth of education in the Washingtonville Central School District."