The first mention of the monastery dates back to 1676, when its churches and monastic cells were wooden. In the 1760s-1770s, the monastery was rebuilt in stone thanks to donations from merchants. From 1752 to 1763, the stone "summer" cathedral of Dmitry of Thessalonica was erected. In the early 19th century, this church was rebuilt and repainted. Services resumed in it in 1829, but work on the interior finishing and paintings continued until 1854. In 1770, south of the cathedral of Dmitry of Thessalonica, a stone "winter" church of Sergius of Radonezh was built with funds from A.F. Kareev, which was expanded in 1863. In the second quarter of the 19th century, a stone fence was built around the monastery, and a three-tiered belfry with gates was constructed.

In 1918, the monastery was closed, its buildings were nationalized and transferred to a local collective farm. A pigsty was placed on the territory of the former monastery, warehouses were arranged in the churches, and a school was opened in the brotherhood building. Later, the collective farm was reorganized, and the buildings began to be dismantled for construction materials. As a result, only ruins remain of the once-famous monastery, linked to the events of the Battle of Kulikovo in 1380.

On January 4, 1996, by decree of the Holy Patriarch and the Holy Synod, the parish of Dmitry of Thessalonica was transformed into the Holy Dmitrievsky Men's Monastery. In early 2010, all the buildings of the monastery were restored.