The Tsiistre school was founded in 1857, when Vastseliina manor allowed one farm’s hay barn to be used as a schoolhouse. According to one recollection, it was located in the middle of the square between the former schoolhouse, dairy and local post office, while others remember it as being on the Kanasaare knoll between the currently extant schoolhouse and the Villapaiu “puddle”. In 1867, the barn was sold to Rogosi municipality and the school building’s older part was built; in 1902 the new classrooms were completed.
Already in 1890, Tsiistre school had an organ, one made by the well-known Kriisa brothers. The new organ that was also bought from the Kriisas in 1924, was destroyed in 1944 during the war. Active musical activity took place in connection with the Tsiistre school – a song choir and orchestra and wind band. Violins, accordions and string basses were made on the spot.
In 1936, it was decided to build a brand-new schoolhouse, but the building was postponed year after year and World War II put a final end to the plans.
In 1920, the school had four grades, in 1930, six, in 1945, seven and in 1960 eight grades. In 1970, the school era came to an end. Over 113 years, many subjects were taught: reading, arithmetic, religion, dancing (at first in secret), singing, love of country, German and Russian, agriculture machinery operation and much more. A total of 55 people are known to have worked as teachers, Kristjan Seim for over 40 years. In 1995, for Kristjan Seim’s birth centenary, the former teachers and pupils gathered and left a memorial stone that depicts the nib of a pen. The stone was designed by Võru architect Tõnu Laos.