The monastery was founded in 1494 by the Venerable Kosma, who became its first abbot. Initially, he was a monk at the Kiev-Pechersk Monastery, but after a vision in which he was commanded to return to his homeland and establish a monastic community, he went to the Vladimir region. There, in a secluded place, Kosma founded the monastery. However, his solitude was short-lived, as the fame of him attracted people wishing to stay close to him. Soon, this place became a monastic settlement, and the brethren persuaded Kosma to become the abbot. He built the Church of the Assumption of the Mother of God and established monastic order. The Venerable Kosma passed away on October 14, 1513, and his relics rest in the cathedral church. The main shrine of the monastery is the Yakhromsk Icon of the Mother of God, which miraculously appeared to the Venerable Kosma. Among his successors are Monk Hilarion and Bishop Mitrofan, who later became the bishop of Voronezh. The monastery has an altar dedicated to Bishop Mitrofan.

From 1666 to 1675, when Bishop Mitrofan was the abbot, the stone Church of the Savior, the cell building, and the cathedral Church of the Assumption were built. In 1694, the Nikolsk Church appeared. The bell tower was erected in 1657, and in 1909, a bell weighing 311 puds was installed on it. During the Soviet era, the bell tower and the stone fence with four towers were destroyed. The two-story Church of the Savior had two altars: one for Bishop Mitrofan of Voronezh and the other for the Venerable Kosma.

In 1863, Abbot Naum established a school for 40 peasant boys at the monastery. In 1879, Abbot Misael became the head. At that time, there were several monks and novices in the monastery. In 1903, under Abbot Veniamin, the cell building was expanded. On the 9th Friday after Easter, a solemn service dedicated to the Mother of God and the Venerable Kosma was held at the monastery, and a fair was opened at the walls of the monastery. In 1689, Abbot Sergius appealed to Patriarch Joachim with a request to free the monastery from duties from the deserted village of Nebyloye. Until the early 17th century, the village of Nebyloye had an independent parish with a wooden Church of the Resurrection of Christ, but during the Time of Troubles, the village was devastated, the church was burned, and the peasants were assigned to other parishes.

During the Soviet era, the monastery was closed and desecrated, and the chapel over the well dug by the Venerable Kosma was destroyed.

In 1992, the Nikolsk Church of the monastery was handed over to the Russian Orthodox Church after unfinished restoration. The church still did not have a dome with a cross, and other buildings housed the Nebyloye Children's Music School and a library. In 1995, the monastery was granted the status of a monastery, which was confirmed by a resolution of the Holy Synod on December 27, 1996. By the order of the Ministry of Culture on June 9, 1997, the entire monastery complex was returned to the Vladimir Diocese of the Moscow Patriarchate of the Russian Orthodox Church. In 2004-2005, major restoration work was carried out, a new bell tower of the Assumption Cathedral was built, and thanks to benefactors, new bells were installed. Today, 12 residents live in the monastery, including 2 hieromonks and 1 hierodeacon. There is also a small farm and a guesthouse for pilgrims.