The rock monastery St. Stephen inhabited by monks in the late 12th century. According to information currently cannot be ascertained, the first founder of the monastery in the year 1191/2, into the holy hermit named Jeremiah. The assembly of the building of the monastery which was founded in the 14th century completed in the 15th and 16th century. First founder of the monastery is the monk, later abbot of it Antonios Kantakouzenos. Antonios in the opinion of some researchers was the son of the Serbian Despot of Epirus Nikephoros II (1359) and a descendant of the great Byzantine family. Secondly founder is Monk Philotheos “ex Sklatainas”, which is referred to as the renovator of St. Stephen.
Theophilos erected a new the old, now Catholic, built the cells and other facilities of the monastery. During his days(1545) the monastery became stavropegic and retained this privilege as in 1743. In 1798 a new church was built dedicated to Saint Charalambos, who in the 17th century referred to as the second patron of the monastery. The 18th and 19th century for the first time several buildings and the abbey was built and took the form it has today. Since 1961 the sisterhood of nuns that lives inside is known for the remarkable social action.
The monastery is located on the southern edge of the cluster of Meteora, just above Kalabaka. Access to the monastery is very easy, since a small stone bridge connects the modern street at the entrance of the monastery. Right and left of the entrance are developed the cells of the monastery. In the eastern part of the yard is the hestia, a small square domed building, the stables and other auxiliary rooms of the monastery.
To the southeast of the yard is the old church of the monastery and the trápeza, which now houses the museum of the monastery skefofylakio. The old church is now used exclusively for religious use of monks and opens for worship only two days of the year at the celebrations of the monastery (December 27 and February 10). Founded in the 15th century. and renovated by Philotheos monk in the 16th century., and is a small single-aisled church with a simple. The painted decoration was executed in two phases. The frescoes of the first phase covering the sanctuary, the nave and the largest portion of liti associated with sponsorship of the abbot of the monastery Mitrophanes and monk Gregory. The paintings of the second phase, which are confined to the western wall of the austere and the lower zone of the pillars that tribelon, made by the painter priest Nicholas Kastrakino, on the initiative of the abbot of the monastery Gregory the 17th century.
In the northwestern part of the yard is the new church, which was built in 1798 and belongs to the type of triconch cruciform church with a spacious plain on the west side and a portico along the northern side of the temple. The surfaces of the walls of the new Catholic who until the 1980s were unadorned now are adorned with works of the famous painter of our time Tsotsonis.