The monastery is first mentioned in documents from 1578, but the exact circumstances and time of its founding remain unknown. The most common version is the story that the monastery was founded by the voivode Bobrok, who commanded the ambush regiment in the Battle of Kulikovo. According to legend, Grand Duke Dmitry Ivanovich Donskoy, returning from Kulikovo Field to Kolomna, vowed to build a monastery in honor of the Nativity of the Mother of God, the feast of victory over Mamai. This vow was fulfilled the following year. According to another version, the monastery was founded by a repentant robber named Bobrenya. Etymologists suggest that the name of the monastery comes from the name of its founder, Bobren or Bobrenya, which is a diminutive of 'beaver.' The monastery was founded not in Kolomna, but on the opposite bank of the Moscow River and may have participated in the defense of Moscow, although it is not mentioned in documents until the end of the 16th century. In the late 19th and early 20th centuries, the monastery was known for its medical assistance to local residents. Abbot Varlaam opened a church-parish school at the monastery on April 14, 1903. Until the closure of the monastery, prayers were said here daily for the warriors who fell at Kulikovo Field. In 1929, the monastery was closed and desecrated, and its buildings were used as warehouses. By 1987, the monastery was in a state of disrepair. In March 1991, after the blessing of Patriarch Alexy II of Moscow and All Russia, restoration work began. The restoration was undertaken by the community of the Church of All Saints in Sokol under the leadership of Boris Kudinkin. A chapel was arranged in the brotherhood building, and restoration of the Cathedral of the Nativity of the Mother of God and the Theodorov Church began. The first rector was Abbot Ignatius Kreksin. On July 18, 1992, Metropolitan Juvenaly of Krutitsy and Kolomna celebrated the first Divine Liturgy in the reviving monastery. After the death of Boris Kudinkin on September 4, 1992, funds for restoration ran out. On June 7, 1993, Patriarch Alexy II visited the monastery. In 1998, the new abbot became Ignatius Zhidkov, who changed the external appearance and internal life of the monastery, contributing to its rapid restoration. Since 2013, the rector has been Abbot Peter Dmitriev. Restoration work continues, a Sunday school operates, and active church and local history work is underway. In 2014, the Society of Lovers of Church History named after the Holy Confessor Theodosius was established at the monastery, and since 2016, a local branch of the Union of Local Historians of Russia has been active. Among the monastery's relics are the Theodorov Icon of the Mother of God, a cross with a particle of the Life-Giving Cross of the Lord, an icon with a particle of the relics of Saint Spyridon of Trimythous, an icon of Saint Sergius of Radonezh, and the Vladimir Icon of the Mother of God.