In 1444 on the outskirts of the city of Borovsk, Kaluga region, at the highest point, where the river of Estrema flows into the river Protva river, was founded by men of the St. Paphnutius Borovsk monastery. The monastery is named after its founder – Abbot Paphnutius.

In 1467 instead of the wooden Church was built of white stone Cathedral called Christmas. Subsequently, the Cathedral has survived. Nativity of the virgin Mary known for the murals, which he was decorated – it was one of the first works of the great icon painter Dionysius. All of Dionisy's frescoes was carried out under the guidance of the elder Simonov monastery — Ikonnikov Mitrophan.

In 1586, during the reign of Tsar Fedor Ivanovich, the Cathedral was demolished and in its place built a new five-domed. Material for construction of the Foundation of the new Cathedral was white stone blocks painted icon painter Dionysius the XV century. Thus, the fragments of the work of the icon painter Dionysius and Ikonnikov Mitrofan has been preserved and stored in the Borovsk Kaluga branch of the state regional Museum and the Central Museum of ancient Russian culture and art named after. Andrei Rublev in Moscow.

In the XVI century the monastery was fenced by stone walls, the monastery began to serve as a border fortification. In the same century was built the Church of the Nativity with a stone refectory. In 1523, was built the bell tower, and in 1688 it was replaced by a bell tower.

Walls and towers Belonging Borovsky monastery belongs to the buildings of the XVI—XVII centuries. There is a theory that St. George, the Armory and Cook towers of the monastery were created under the guidance of the famous architect, author of the buildings of the White city in Moscow, Smolensk Kremlin and Simonov monastery - Fyodor Savelyevich Horse. However, the specialists of our time claim that the walls of the St. Paphnutius Borovsk monastery and the ancient round tower, which survived until our days, were built after the erection of the Cathedral and bell tower by the same architect. Other towers: taynitskaya, St George's were rebuilt after the devastation of the monastery during the time of troubles in 1635 master trom Serotinum, and the last tower: the Watchtower and the Entrance was restored in 1636 or after. It should be noted that the fortress was designed for the defense outdoor "legit" wall, which is characteristic of the FOURTEENTH and fifteenth centuries, t.to. the tower, built at a small distance from each other, the floor side of the fortress were designed for active resistance and simultaneously performs the function of the Central architectural facade of the monastery.

In 1610 from the poles, the monastery was defended by Prince Mikhail Volkonsky, but he was taken and burned.

In the period of reforms of Patriarch Nikon, Bishop Paul of Kolomna, hieromonk Polict Borovsky and some other of the leaders of the monastery were against Church reforms. Subsequently, the opponents of reform were repressed, and Bishop Paul of Kolomna and hieromonk Polict Bohr were executed.

Since the reforms of Patriarch Nikon, the St. Paphnutius Borovsk monastery began to decline. During the reign of Catherine II in the monastery left 33 monks and novices, and almost all belonged Belonging Borovsky monastery estates were selected. In 1812, the French burned the monastery, but after the fire it was able to restore.

In 1923 the property belonging Belonging Borovsky monastery was transferred to the leadership of the General Directorate of museums, but soon it was placed a penal colony, and after – the agricultural school. In the 1960-ies, when restoration work was found 194 white stone block, and only 29 fragments of stories decorative painting, Dating from the early sixteenth century.

In 1991 the monastery was given to the Russian Orthodox Church, and in March of the same year it was opened. The relics of the monk Paphnutius, the founder of the monastery, are stored in the Nativity Cathedral.