The Assumption Church in the Oryol Holy Assumption Monastery was built in 1693. In 1820, the monastery became the residence of the Oryol bishops, and the monks were transferred to the Mtsensk Peter and Paul Monastery. By the end of the 19th century, there were several churches on the monastery grounds, including the Assumption Church, the Church of John the Baptist (1700), the Trinity Church with the burial vault of the Kochubey family (1845), the Trinity Cathedral (1879), the Archbishops' House with a chapel, the consistory, and utility buildings.

Bishops of Oryol Nikodim (1786-1839), Polikarp (1798-1867), Juvenal (1817-1882), Iriney (1836-1904), Elets vicar bishop Mitrofan (1863-1914), as well as the current Archbishop of Oryol and Livny Paisiy (in the world Pavel Nikolayevich Samchuk) (15.08.1930-20.03.2008) were buried in and near the Assumption Church.

In 1980, the building of the old Assumption Church was completely dismantled. In 1990, the construction of a new Assumption Church began, and in 1992, the territory of the former monastery was transferred to the Oryol-Bryansk Diocese. Monastic life resumed here in 1996. In 2002, the church in honor of the Assumption of the Holy Virgin was consecrated, built according to the design of architect M.B. Skorobogatov.