Located 3 kilometres south of the capital Sofia's neighbourhood of Dragalevtsi, Dragalevtsi Monastery was established by Tsar Ivan Alexander in 1345 at the time of the Second Bulgarian Empire.
After Sofia fell to the Ottomans in 1382, the monastery was disbanded and its buildings destroyed. It was rebuilt in the second half of the 15th century with the financial support of local feudal lord Radoslav Mavar and rapidly developed into a repository of Bulgarian cultural records. In 1612, while staying at Dragalevtsi Monastery, the monk Job Kasinets from Timișoara wrote the Boyana Beadroll, a list of medieval Bulgarian rulers. The document shows the extent to which medieval rulers were remembered in 17th-century Bulgarian lands. Other manuscripts completed in this period at the monastery's scriptorium include Priest Nicholas' Gospel of 1469, the Dragalevtsi Gospel of 1534 and a psalter finished in 1598.
Today only the monastery church survives from what was a significantly more extensive complex of buildings in the 15th century. The church was expanded in 1818 and 1932. In the late 19th century, Dragalevtsi Monastery was often visited by national hero Vasil Levski, who used it as a centre for his revolutionary activities. The monastery is currently inhabited by nuns.
The monastery church, eponymously known as the Church of the Holy Mother of God, measures 12 by 5 metres. It has a single apse and a single nave. Architecturally, it shares many features with other contemporary churches in the Sofia region. Mural portraits of Radoslav Mavar and his immediate family as church donors (ktetors) were painted on the inside of the monastery church. In addition to these, other 15th-century frescoes also survive, alongside 16th- and 17th-century paintings. The frescoes of warrior saints Demetrius of Thessaloniki, George and Mercurius on the upper reaches of the west facade date to 1475–1476.
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