Exact documentary information about the time of the monastery's foundation has not survived to this day. The first hermit, Fyodor, settled on the banks of the Ustya River, arriving from Novgorod. Three years later, Pavel joined him, and together they became the first inhabitants of the new male monastery.

In 1363, Sergius of Radonezh arrived in Rostov land to resolve conflicts among local princes. This was a time when Rus was strengthening, preparing for a decisive blow against the Horde. To unite the principalities and coordinate actions, fortified monasteries began to be built around Rus.

Fyodor and Pavel turned to Sergius of Radonezh for help in establishing a new abode. Sergius, in turn, convinced Prince Konstantin Vasilyevich to support them. The monastery was dedicated to the holy princes Boris and Gleb, who are especially venerated in Rus.

The monastery was located on the northeastern borders of the Moscow state and quickly developed, attracting monks and craftsmen. The first wooden churches and cells were built here, and the territory was surrounded by a strong wall that protected against Tatar and Polish-Lithuanian invaders.

The fame of the monastery spread quickly, and pilgrims flocked here from all directions. Sergius of Radonezh often visited the abode, and Grand Prince Vasily II the Dark found refuge here from persecution. In the monastery, he baptized his son, the future Tsar Ivan III.

According to legend, the legendary Peresvet became a monk in the monastery. The abode enjoyed special favor from the rulers of Rus, which contributed to its prosperity. As a result, the monastery became one of the largest landowners in Russia, owning 360 settlements and 22,000 desyatinas of land.

A special chapter in the history of the monastery is associated with the Venerable Irinarh (Ilya), who, after 30 years of trade, took monastic vows and led a life of seclusion. Kuzma Minin and Dmitry Pozharsky came to Irinarh for blessings.

In the 18th century, the monastery thrived and became the center of the Borisoglebskaya sloboda, around which fairs were held and crafts developed. However, at the end of the century, Catherine II seized part of the sloboda for Count Orlov, leading to the loss of many valuables and weakening the abode.

With the advent of Soviet power, the monastery was abolished in 1924, and its premises were transferred to the Rostov Museum. Many icons and bells were destroyed, but thanks to the intervention of the People's Commissariat for Education, the bell tower was preserved. Services continued until 1928.

From the 1930s, various institutions were housed in the monastery, including the police and post office. The museum was closed from 1954 to 1961, but then the entire territory was returned to it, and restoration work began.

In 1994, part of the territory was transferred to the Orthodox Church, and in 2015, the entire abode came under its management.

The first stone buildings appeared in the 16th century. The Borisoglebsky Cathedral, laid in 1522 by the order of Vasily III, is attributed to architect Grigory Borisov. The cathedral was rebuilt multiple times, and during the 1925 reconstruction, evidence of its five-domed appearance was found.

The stone Annunciation Church was also built in the 16th century as a refectory church. A century later, it underwent significant alterations.

On the territory, a two-story abbot's house from the 16th century has been preserved, which was rare and testified to the wealth of the abode. To the north is the building for the brethren.

The brick wall was erected during Ivan the Terrible. During the Time of Troubles, it protected against Polish-Lithuanian troops. Historians disagree on whether the monastery was captured or the Poles retreated. It is only known that after the invasion, the fortifications were rebuilt.

The abode is adorned with defensive walls with towers and the gate churches of Sergievsky and Sretensky. From the monastery's fortifications, a beautiful view opens up over the entire territory and surroundings.