The monastery, founded thanks to the ascetic activities of Sergius of Radonezh, was one of many that emerged at that time. Its first abbot was Sergius's disciple, Grigory Golutvinsky, appointed by the Kolomna bishop Gerasim. Sources mention the Kolomna bishop Grigory, which may indicate that this was indeed the venerable Grigory Golutvinsky. The legends of the monastery say that Sergius not only chose the site for the monastery but also laid the first church in honor of the Theophany. In the basement of the Theophany church, one can still see the remnants of its foundation, known as the 'stones of the venerable.' According to tradition, Sergius indicated to the brethren the place for a well, and soon a spring gushed forth, which functioned until the mid-20th century, when the monastery was closed, and the spring was filled in and concreted over. Before the monastery's closure in 1929, it housed relics associated with Sergius, such as his staff, cross, and vestments. The monastery on the Oka River also served a defensive function against Tatar raids, which contributed to its development.

In the 15th century, the monastery flourished, its monastic life strengthened, a winter church in honor of Sergius of Radonezh was built with a high basement and auxiliary rooms, as well as a brotherly refectory, kitchen, and bakery. Between the Sergius and Theophany churches, a bell tower was erected, which was dismantled in the late 18th century. The monastery owned lands in Moscow and Golutvinskaya sloboda, and in 1472, Prince Yuri Vasilievich gifted it the villages of Rozhek and Malivka. In 1480, Grand Duke Ivan III visited the monastery before his campaign against the Tatar Khan Akhmat.

When we entered the monastery, we were greeted and led into the large church of the Theophany with a high entrance and a gallery with three doors. The church is ancient; we attended evening prayers there and then went to another church in the refectory dedicated to Sergius. Between these churches stood a bell tower with a dome reminiscent of church domes.

The monastery thrived, visited by Tsar Ivan the Terrible, and it had a rich library. In April 1912, the revered elder Varsonofy Optinsky became the abbot, a year before his death. The monastery was closed in 1929, and in 1994 it was handed over to the Moscow diocese, and divine services resumed in December of that year. In 1995, the Moscow diocesan spiritual school was relocated here, later transformed into the Kolomna Orthodox Theological Seminary.

In October 2012, the buildings of the eastern brotherly and western hotel block, as well as other structures, were transferred to the seminary for the monastery's management.