The Monastery complex is formed in the period before the conquer of the Ottoman Empire, meaning in the first half of the XIV century. As the time went by, the city of Chebren started to disappear and only the monastery remained. The Monastery at the beginning of the XVIII century had a school with priests who performed worship servicein the churches throughout the Mariovo area and it was very active up to the first decades of the XX century. In its centennial existence, it was renovated couple of times due to the frequent fires, thefts and destructions.
There is some data which says that during the First World War, some parts of the monastery were ruined and destroyed. The Monastery complex was protected with a fence wall which does exist even at present, yet it is also partially demolished.