According to some records the monastery existed as early as the time of Crusades (11th – 13th c.) and in 1419 it was razed to the ground by the Turkish. Later it was restored.
For the first time the monastery was mentioned in a handwritten note from 1693. In 17th and 18th century Kalugerovo Monastery was a centre of literary activities.
During the April rising (1876) the monastery was set on fire by the Turkish. In 1906-08 it was rebuilt.
A marble slate from the time of the Roman emperor Julian has been preserved as well as a few marble slates from 19th and the beginning of 20th century with inscriptions in Bulgarian.
The monastery is active, without monks.