In 1969 and 1970, during the study of the modern Nativity Cathedral by M.Kh. Aleshkovsky and B.L. Altshuller, the foundations of an ancient temple were discovered, dating back to the second half of the 14th century. This led to the assumption that the temple was built with the participation of the holy and righteous Dmitry Donskoy. However, modern researchers attribute the cathedral to a later period, the early 15th century, based on the characteristics of stone processing. It is possible that a wooden church preceded the stone one. The appearance of the white-stone cathedral is quite clearly reconstructed: it was a tall three-apsidal temple made of smoothly hewn blocks, single-domed, adorned with elegant carvings. The facades had a three-part elevated structure, and the roof was likely topped with kokoshniks, on which rested a drum with a helmet-shaped dome and a cross.

In 1753, Archimandrite Ignatius appealed to Bishop Gabriel of Kolomna and Kashira with a report about significant destruction in the cathedral and monastery. The archimandrite and the brotherhood, testifying to extreme poverty, asked the Synod to fulfill the will of the late bishop Savva and allocate three thousand rubles for the construction of the monastery. The request was granted, and in 1757, the construction of a new brick cathedral began under the guidance of Abbot Anthony. The monastery was then managed by Abbot Andrew. In 1763, an Officer's inventory was compiled, describing the state of the construction and the monastery. It was evident that the temple was almost ready, but the bell tower was still unfinished, with only part of the first tier laid. Catherine II was preparing a monastic reform known as secularization, during which monastic lands were transferred to the treasury, and monasteries were divided into classes, receiving salaries accordingly. Bobrenev Monastery found itself among such monasteries. In 1764, it was left off the state list, which had a detrimental effect on it for the next twenty years. The nearly completed construction of the new cathedral was halted. In 1790, the monastery was revived, and under Bishop Athanasius, active construction began. In 1790, the Nativity Cathedral was completed, its bell tower was finished, and the white church, like a candle, illuminated the Kolomna plain. The monument is characterized by a majestic-archaic appearance, devoid of the lavish decorations typical of baroque, which confused researchers who dated the bell tower to the 17th century, although it was completed in 1790. In 1917 and 1918, the monastery was plundered, and the gallery of portraits of Kolomna bishops was lost. According to legend, during the Civil War, there was an attempt to rob the Theodorov Icon, and one of the church servants was killed. In the early 1920s, the monastery was closed. In March 1991, His Holiness Patriarch Alexy II of Moscow and All Russia and the Holy Synod blessed the reopening of Bobrenev Monastery, and restoration work immediately began. On July 18, 1992, His Eminence Metropolitan Juvenal of Kolomna and Krutitsy celebrated the first Divine Liturgy in the renewing monastery.