The first church in the monastery was built between 1629 and 1645 during the reign of the first tsar from the Romanov dynasty, Mikhail Fyodorovich. The main altar was consecrated in honor of the Kazan Icon of the Mother of God. A chapel in honor of St. Alexius, the Man of God, was arranged in the stone refectory church with funds from Ivan and Peter Alexeyevich.

Under Catherine II, the monastery was surrounded by a stone fence, as seen in the 1776 plan, but the cells remained wooden until the monastery's closure in 1922.

In 1823, under Abbess Augusta, a chapel was arranged on the northern side of the refectory in honor of the Czestochowa Icon of the Mother of God.

From an essay by Alexei Znamensky in the Kaluga Provincial Gazette of 1889, we learn that all buildings, except for the church, inside the monastery were wooden. However, in the city plan, the monastery was marked as stone, so on November 11, 1828, Abbess Angelina sent a request to the Kaluga governor asking to change the city plan in the area of the monastery and allow wooden buildings within its enclosure. She explained that the monastery is located at the foot of a hill, surrounded by a stone fence and greenery, and that most of the cells are personal property of the nuns, who cannot afford to rebuild them. The abbess requested permission to build wooden cells more suitable for sick and elderly nuns, and received this permission.

Bishop Philaret (Amphiteatrov) wrote to the capital in 1820-1821 that there was only one women's monastery in the Kaluga diocese, and the conditions there were so cramped that the sisters could hardly accommodate themselves.

Under Abbess Angelina (Yanovskaya), the construction of a new three-altar church began, for which the old one was dismantled.

The consecration of the new cathedral church took place on July 6, 1903. According to the description of pre-revolutionary local historian D.I. Malinin, the building is made in the Byzantine style with five domes, of which the central one has a diameter of 11 arshins. The dome is supported by four columns, the arches are high, and the choir is located on the western side. The iconostasis is four-tiered, with contemporary painting.

After the revolution, the monastery was closed by decree in 1918, but the nuns restored it as the first women's labor artel. In 1922, the monastery was finally abolished, and all 118 nuns were evicted within two weeks. They, like many believers, were subjected to repression, dying in prisons and camps. During the fascist occupation, the Germans set up a ghetto on the monastery grounds, which they burned upon retreat, and all the wooden cells were destroyed.

The monastery was revived as a monastic community on February 10, 1992. The community was formed from the sisters of the Sisterhood in honor of the Holy Martyr Grand Duchess Elizabeth, which existed under the charitable department of the diocese. The sisters lived in a small wooden house next to the Nikolsky Church in Kaluga, as the former territory of the Kazan Women's Monastery and the monastery cathedral had not been returned to the Church. This house long served as the residence of diocesan archbishops during the persecution of the church.

With the arrival of Archbishop Clement to the Kaluga diocese, the building of the seminary was returned to the diocese, and the community settled in this house.

On December 26, 1995, the Holy Synod blessed the opening of the Kazan Women's Monastery. From 1995 to 2007, the monastery was located in the building of the former Spiritual School, which also housed the Orthodox Gymnasium and the Kaluga Spiritual School. The domestic church in honor of St. Guriy of Kazan, consecrated by Archbishop Clement in 1995, was the monastery's church.

The building of the cathedral church in honor of the Kazan Icon of the Mother of God has still not been transferred to the diocese. However, in 2012, a plot of land was allocated next to the cathedral church for the construction of a sisterhood building. Although the plot is not very suitable for construction, this event instills hope for the revival of the oldest women's monastery in the Kaluga diocese.

On March 19, 2017, services are held in the church of St. Guriy of Kazan on Sundays and holidays.