In 1444 on the outskirts of the town of Borovsk, Kaluga region, at the highest point where the river flows into the river Istrema Protva was founded male Pafnutyevo-Borovsky monastery. The monastery is named after its founder - the abbot Paphnutius.

In 1467 instead of the wooden church was built of white stone cathedral, called Christmas. Subsequently, the cathedral has not been preserved. Nativity of the Virgin is famous for the fact that the painting, which he was decorated - it was one of the first works of the great Dionysius. All the paintings were carried out under the leadership of Dionysius the Elder Simonov monastery - Ikonnikov Mitrofan.

In 1586, during the reign of Tsar Fyodor Ivanovich, the cathedral was demolished and in its place erected a new five-domed. The material for the construction of the foundation of the new cathedral were the white stone blocks with Dionysius frescoes of the XV century. Thus, fragments of the works of Dionysius and Ikonnikov Mitrofan survived and stored in Borovsk branch of Kaluga State Regional Museum and the Central Museum of Ancient Russian Culture and Art. Andrei Rublev in Moscow.

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

Walls and towers Pafnutyevo-Borovsky monastery belongs to the buildings XVI-XVII centuries .  There is a version that George, the Armoury and table tower of the monastery were created by the famous architect, author of White City buildings in Moscow, Smolensk Kremlin and the Simonov Monastery - Fyodor Savelyevich Horse .  However, experts of our time claim that the wall Pafnutyevo-Borovsky monastery and the most ancient round tower, which survives to this day, were built after the construction of the cathedral and the bell tower by the same architect .  The rest of the tower: Taynitskaya, George had been restored after the destruction of the monastery in the days of the troubled times in 1635 Trofim Sharutin master, and the most recent tower: Watchdog input and restored in 1636 or after .  It should be noted that the plan was a fortress designed to defend the floor "pristupnaya" wall, which is characteristic of the XIV-XV centuries, that is, . to .  Tower, built on a small distance from each other, through the outdoor side of the fortress were designed for resistance and at the same time perform the function of the central architectural facade of the monastery . 

In 1610, the Poles defended the monastery Prince Mikhail Volkonsky, but he was captured and burned.

During the reforms of Patriarch Nikon, Bishop Paul of Kolomna, monk Poliekt Borovsky and some other leaders of the monastery were against church reforms. Subsequently, the opponents of reform were repressed, and Bishop Paul of Kolomna and monk Poliekt Borovsky were executed.

After the reforms of Patriarch Nikon, Pafnutyevo-Borovsky monastery began to decline. During the reign of Catherine II in the monastery left 33 monks and novices, and almost all belonged Pafnutyevo-Borovsky monastery estates were selected. In 1812, the French burned the monastery, but after the fire it was restored.

In 1923, property belonging Pafnutyevo-Borovsky monastery was transferred to the leadership Glavmuzeyu, but soon it was posted a penal colony, and after - the agricultural school. In 1960, when restoration work was found 194 white stone blocks, and only a 29-minute fragments of stories decorative painting, dating from the beginning of the XVI 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 St. Paphnutius of Borovsk, founder of the monastery, are stored in the Cathedral of the Nativity.