In 1858, hieromonk Feoktist was appointed as the builder of the monastery. Thanks to the generosity of the church founder, Feoktist was able to quickly erect a new church of the Entry into Jerusalem on the site of the old ruins, dedicated to the Fedorov Icon of the Mother of God. The construction was completed in 1860. The church was built according to a quality project in the style of late classicism. Although its exterior decoration was somewhat restrained, the overall impression of the building was dignified. The majestic and calm appearance of the church harmonized with the ascetic spirit of the ancient monastery. The construction avoided the influence of "degrading classicism" and the gaudiness of the "Russian style."

In 1917 and 1918, the monastery was subjected to looting, and the gallery of portraits of Kolomna bishops was lost. In the early 1920s, the monastery was closed, and it gradually fell into disrepair. The brotherhood building was converted into apartments for workers of the state farm, while the abbot's building housed an elementary school, a medical station, and accommodation for workers. For decades, the church was used for storing mineral fertilizers. However, even in the mid-20th century, part of the monastery library remained in the sacristy. The final blow was the establishment of a garage in the church of the Fedorov Icon: the altar wall was breached, and tractors drove into the church through it. Monastery books and manuscripts were thrown into the street, and ultimately, the monastery turned into a dump.

In March 1991, His Holiness Patriarch Alexy II of Moscow and All Russia and the Holy Synod blessed the reopening of the Bobrenev Monastery. Since then, the restoration of the monument associated with the Kulikovo victory began. The restoration was undertaken by the community of the Moscow Church of All Saints in Sokol, under the leadership of elder B. S. Kudinkin. A small house church was opened in the brotherhood building. On July 18, 1992, His Eminence Metropolitan Juvenaly of Kolomna and Krutitsy conducted the first Divine Liturgy in the restoring monastery. On August 29, 2005, the solemn Great Consecration of the restored Fedorov Church took place, also performed by Metropolitan Juvenaly.