The history of the Orzhev Monastery is closely linked to the noble family of Tisheninov. Vasily Markovich Tisheninov, a college adviser, and his wife Nadezhda Vasilievna owned the estate of Tisheninovka, located near the village of Orzhevka in the Kirsanov district. Nadezhda Vasilievna dreamed of establishing a monastic community in her estate and bequeathed to her children to realize this idea. After the tragic death of her brother Nikolai and sister Vera, Maria Vasilievna Tisheninova took on the execution of this will. On July 6, 1859, she appealed to the Holy Synod with a request to allow the opening of a women's community in her estate.

At first, Maria Vasilievna had neither people to create the community nor leaders. However, she was confident that such people would be found. At a meeting of the Tambov Spiritual Consistory, it was noted that Tisheninova could not become the head of the community due to illness in her legs and arms, and could not yet present women willing to live in the community, but hoped that over time many, especially orphans, would want to join.

The Synod, considering that Tisheninova would take on the material support of the community, made a positive decision. On May 14, 1864, a decree was issued approving the opening of a women's community in the village of Orzhevka. This date is considered the day of the official opening of the monastery. The decree also stated that initially, those admitted to the community would be accepted without the right to be tonsured as nuns. The staff was set at 50 people, with the possibility of increasing at the discretion of the head. It was specified to accept individuals not connected with other monasteries. A significant contribution to the opening of the monastery was made by S.V. Sosulnikov.

The monastery actively engaged in charity. In 1877, it donated 52 arshins of canvas, 7 shirts, 2 sheets, and copes to the Kirsanov branch of the Society for the Care of the Sick and Wounded. The sisters also donated funds to the church of the spiritual school in Tambov, to a missionary school, to the construction of the Ashgabat Cathedral, and to the society for the blind. In 1904, 12 girls aged 9 to 12 were educated in the Orzhev Monastery school-orphanage. The diocesan authorities particularly noted the care for the students and expressed gratitude to the abbess for her kind attitude towards the children. In 1904, the monastery hospital admitted 1,098 people, 20 of whom were treated as inpatients.

During the war of 1914-1918, the material condition of the monastery worsened. By the end of 1914, only 6 rubles and 51 kopecks remained in the treasury. Despite this, the leadership decided to maintain a small hospital for the wounded. In 1914, there were 46 nuns and 194 novices in the monastery. The internal life of the monastery corresponded to the monastic rule. The "unfailing" Psalter was read with the commemoration of the deceased and an akathist before the main shrine of the monastery, the Bogolyubskaya Icon of the Mother of God, gifted by the Moscow merchant T.D. Zotova in 1864.

Every year on July 1, it attracted many pilgrims. Among the notable figures of the monastery was schemamonk Dorothea, but details of her life have not survived.