The monastery was founded in the late IX century during the reign of the Macedonian dynasty, by the first wife of Leo the Wise, who made a lot of valuable donations. In addition to the land that fell into the ownership of the monastery, it was given unique shrines, such as: the Honest Head of St. Anastasia and a part of her right foot, as well as the scepter of Emperor Leo VI, lost during the fire of 1821, which destroyed the monastery to its foundation.
There is no much information about the first years of the monastery, but there is a version that Saint Theophania was one of its founders, as the monks who restored the monastery after the fire decorated the iconostasis with the icon representing her holding the monastery in one hand and the scepter in the other.
With the capture of Greece by the Ottoman Empire, the monastery of St. Anastasia played an important national and enlightening role. It was here that the inhabitants of the Halkidiki Peninsula were looking for support during these difficult times. Adults worked on the monastic fields, while children taught literacy. Later, a real school appeared here, where the teachers were the monks themselves.
At the end of the 16th century, the Patriarch of Alexandria Meletios Pigas, proclaimed the freedom of the monastery. The sixteenth century was the century of greatest prosperity. Many educated monks appeared from the circle of those children, and created some manuscripts known all over the world.
Difficulties began in the first half of the XVII century, when the Ottomans took away the monastery’s ownership right over of all of its property and asked for a ransom. To find money, the monastery sought help not only in Greece, but also in Russia. In 1644 the delegation went to Moscow to meet the Tsar Mikhail Fedorovich, who agreed to help the Orthodox brothers. In 1652, for the same purpose, the delegation went to Moscow to meet the Tsar Alexei Mikhailovich.
The Holy Great Martyr Anastasia lived in the 3rd c. in Rome and came from a noble family of a patrician. Her husband, Poplionas, an idolater, was enraged to learn that his wife was secretly visiting prisons, handing out food to prisoners, supporting them with a kind word, and preaching Christianity. When the exhortations did not have the proper effect on Anastasia, Poplionas delivered her to the hands of justice. In 290, Anastasia, after much torture, by the order of Diocletian, was burned at the stake.
Today, pilgrims from all over the world come to this monastery to pray to Saint Anastasia for the relief of the prisoners’ fate and for the strengthening of faith.