The exact date of the founding of the St. Nicholas Chernoostrov Monastery is unknown, but according to legend, in the 14th century, the Obolensky princes built a church in Maloyaroslavets in honor of St. Nicholas the Wonderworker.

Archimandrite Leonid Kavelin, the first historian of the monastery, believed that the monastery was founded later, in the early 16th century, after the city was annexed to the Grand Duchy of Moscow.

In the 17th and 18th centuries, the monastery was little known and had only a few monks who lived off the monastery land. The monastery was often converted to self-sufficiency and even abolished due to lack of funds.

The revival of the monastery is associated with merchant Terenty Elizarovich Tselibeev, who dedicated his life and resources to its restoration. In 1791, he and his niece Natalia Venevtseva appealed to the Holy Synod with a request to revive the monastery. Construction progressed slowly, and initially, there were only four people in the monastery.

In 1809, at the request of the residents and merchant Tselibeev, the builder of the monastery became hieromonk Makary (Fomin) from Optina Pustyn. He accepted the monastery in a semi-ruined state. Within a year, the church, bell tower, fence, and other buildings were repaired. However, the war with the French interrupted the work, causing serious damage.

On October 12, 1812, a battle with Napoleon's troops took place near the walls of the monastery, which influenced the fate of Russia and Europe. The monastery was burned and looted, but the image of the Savior Not Made by Hands remained unharmed. Eight thousand Russian soldiers are buried in three burial mounds.

A month after the invasion, services began in the semi-ruined church, and in the spring of 1813, Father Makary began the restoration of the monastery.

In 1817, the monastery was included in the staff in memory of the victory. Emperor Nicholas Pavlovich donated "vestments for the cathedral service." The external arrangement was completed under Archimandrite Makary, who died in 1839 and was buried next to T.E. Tselibeev.

The internal arrangement of the monastery, modeled after the best Russian monasteries, was completed by Elder Anthony (Putilov) from Optina Pustyn in 1840. Under him, the construction of the Nicholas Cathedral was completed, consecrated in 1843. The Chapel of the Transfiguration of the Lord was consecrated in 1849.

In 1860, at the request of Major F.M. Maximov, a chapel in honor of St. George the Victorious was built over the graves of the 1812 warriors.

By the early 20th century, the monastery was fully restored: the brotherhood building and hotel were constructed, and the Church of All Saints was consecrated. The monastery had running water, a greenhouse, a pond with fish hatcheries, and a brick factory. A church-parish school was opened. However, prosperity did not last long: after the October Revolution of 1917, the monastery was devastated, and by 1926, all buildings were in a state of disrepair. In the mid-1920s, the monks left the monastery.

After many years of ruin, in 1991, the monastery was transferred to the Kaluga Diocese. It is now almost fully restored and conducts charitable and educational activities. Since 1993, the monastery has operated a shelter-pension "Otrad" for girls from disadvantaged families. The construction of the children's shelter complex is overseen by the charitable foundation "Connection of Generations," headed by Major General A.I. Kotelkin. The Faculty of Journalism of RSGU and a women's choir also operate at the monastery.