The Church of St. Sergius of Radonezh with the abbot's residence was built at an unknown time. However, it is known that the founder of the monastery, Dmitry Prilutsky, met with the venerable Sergius of Radonezh. This meeting took place in 1354 in Pereslavl, where Sergius came for his ordination as a presbyter. Under the influence of conversations with Sergius, Dmitry introduced a communal rule in the Nikolsky Monastery, previously unknown in Northern Rus. According to tradition, Sergius also visited his spiritual friend in his monastery and prayed in the Nikolsky church.