The Kirzhach Monastery is mentioned in the land books of 1627-1631, which included the Church of the Annunciation of the Most Holy Theotokos, the chapel of Tsar Constantine, and the Church of St. Sergius the Wonderworker with a refectory, both made of stone, while the bell tower was wooden. The monastery was surrounded by a stone fence 100 fathoms long and 70 fathoms wide, with two round stone towers at the corners and a tent over the holy gates.

In the inventory of the Trinity-Sergius Lavra and its monasteries from 1642, it is noted that the holy gates were stone with an empty church above. In the early 1840s, the family of Alexander Petrovich Solovyov lived in Kirzhach, who, after studying icon painting at the Trinity Lavra, became the elder of the Annunciation Church in 1844. He diligently worked on the improvement of the temples and buildings of the monastery. During his 17 years of service, the churches and monastery fence were decorated and rebuilt, and the holy gates were also restored.

After the monastery was closed by the Bolsheviks, it fell into disrepair until the early 1960s. In 1963-1964, the Annunciation Cathedral and the Church of the Merciful Savior were partially restored, limited to external whitewashing. In 1983, the authorities of Kirzhach decided to use the architectural monuments for public needs: a youth club was planned to be opened in the Savior Church with arcade machines, and a museum in the Annunciation Church. For this purpose, the holy gates were restored. However, the work carried out in the 1980s-1990s was done improperly, leading to the emergency condition of the buildings.

In the summer of 1990, the Annunciation and Savior Churches were returned to the Russian Orthodox Church. Pilgrims and parishioners began to enter the monastery through a gate in the eastern wall, while the holy gates remained closed. The entrance arch became an impromptu storage for construction materials left over from the restoration, as well as traces of the activities of the bread factory, which operated until the mid-1990s in the neighboring church in honor of All Saints.