The monastery’s establishment dates back to 1345, the time of the Second Bulgarian State (which ended with the Ottoman invasion in Bulgarian lands at the end of the 14th century) and the reign of the Bulgarian King Ivan Alexander (1331-1371). In contrast to most other Bulgarian monasteries, Virgin Mary of Vitosha was saved from destruction by the Ottoman conquerors. Nevertheless, a few years later, it was abandoned by its monks. Soon afterwards, in 1476, it was renovated and brought back to life by a Sofia boyar, Radoslav Mavar. During this reconstruction, the small church of the monastery was decorated with beautiful frescoes, most of which have been preserved to present days. Among these, the portraits of Radoslav Mavar, his wife and two sons carry the highest ethnographic and artistic value. In the 17th century, the central part of the church was decorated with new wall paintings. In 1932, the church was expanded with the attachment of a new building to it - currently, the two parts represent an integral whole with the one sign of their distant époques being the different architectural styles.

In addition to its valuable frescoes from three different time periods, the monastery is also famous for hosting a so-called cell school during the Ottoman rule, and producing the Dragalevtsi Testament. Besides being a cultural and educational centre (with its apogee in the 15-16th centuries), the Dragalevtsi monastery is a typical representative of the still-preserved Bulgarian monasteries, as it took active part in the secret revolutionary activity against the Turks in the mid-19th century. The abbot of the monastery, Genadii, was a close friend and collaborator of the national hero Vassil Levski, and helped him actively in the organisation of revolutionary committees in the Sofia region. While Father Genadii served as a mailman of the secret revolutionary committee of Sofia, Vassil Levski hid more than once in the monastery while travelling in the country with Ottoman troops after him. After one of the most active members of the revolutionary organisation, Dimitar Obshti, was arrested while the Turkish authorities became aware of Genadii’s underground activities, Father Genadii escaped to Serbia in order to joint another revolutionary, Panayot Hitov, and continue his work from there. Genadii’s escape however did not put an end to the monastery’s involvement in the preparations for a national uprising, as his successor at the monastery, Father Ignatii of Rila, restored the secret revolutionary committee of Sofia and followed in the steps of Genadii.