According to a legend, a shepherd from the village of Kuremäe witnessed a divine revelation near a spring of water to this day venerated as holy.
Later in the 16th century, locals found an ancient icon of Dormition of the Mother of God under a huge oak tree.
In 1888, the Russian Orthodox Church sent a nun from the Ipatiev Monastery in Kostroma to establish a convent in Pühtitsa.
Following the second invasion and occupation of Estonia by the Soviet Union in 1944, the convent managed to survive despite the uneasy co-existence with the Communist authorities.
Patriarch Alexius II who was the bishop (later the archbishop) of Tallinn and Estonia in the 1960s was instrumental in the fight to keep the convent from closure.