According to the 15th-century Cypriot chronicler Leontios Makhairas, after the end of the First Ecumenical Synod in Nicaea (325), Helena went on a pilgrimage to the Holy Land when she discovered the three crosses on which Jesus and the two thieves had been crucified.

[citation needed] She had them excavated and wanted to bring them to Constantinople, but she is said to have left one of these crosses in Cyprus during an involuntary visit caused by shipwreck.

After several unsuccessful attempts to get the Holy Cross out of that mountain, Helena decided to leave a piece there, and built a small chapel to accompany it.

In addition, visitors will find two small chains which were worn by Saint Panaretos, Bishop of Paphos, during his life, and which were in direct contact with his body.

The oldest written reference dates from the Byzantine period, and it proves that Stavrovouni had been an important religious centre since the 4th century.

In its long history, Stavrovouni went through times of great poverty and hardship caused by the numerous invasions by foreigners on the island.

The walls, the church, the iconostasis, and the monks' cells in Stavrovouni were almost completely destroyed during a great fire in 1888.

The records suggest that the monastery had no monks for a period roughly between the 16th and the 19th century, a time when the Turks ruled the island.

In 1890, three more Cypriot monks, again from Mount Athos, joined him at Stavrovouni: Fathers Varnavas – who would become the next Abbot – and his two brothers Kallinikos and Gregorios.

Other monks attempted to move to, and revive, the Monastery of Saint John the Baptist in Mesa Potamos in Limassol.

Saint Filoumenos the Cypriot martyr, member of the Brotherhood of the Holy Sepulchre, is one such important monk who started his monastic life at Stavrovouni.

The Hieromonk Kyprianos († 1955) is another significant figure who lived at Stavrovouni; he was known for his strict way of life and his helpful advice to the people of Cyprus.

The legend of the foundation is recorded in these pictures: St. Helena in a brilliant red garment and the Finding of the True Cross in Jerusalem.

Moreover, locals visit the monastery, especially on feast days, and follow the monks in their worship programme – in liturgy, vespers, etc.

This rule is called avato (Greek: άβατο, meaning: entry is prohibited), and it is analogous to the strict life of monks in Mount Athos[5] where women are not allowed to enter.