The Kaluga St. Lawrence Monastery is the oldest monastery in the city of Kaluga and the entire Kaluga region. It is dedicated to St. Lawrence of Kaluga, who lived in the house of the pious prince Simeon. Taking on the feat of foolishness for Christ, Lawrence preferred solitary prayers on a hill near Kaluga, next to the Church of the Nativity of Christ. There he built himself a hut for prayer and fasting. In ancient icons preserved in the Kaluga region, St. Lawrence is depicted barefoot, in a shirt and sheepskin, with an axe on a long handle.

Lawrence remains the prayer patron of the Kaluga land. In 1512, when the Tatars attacked Kaluga, he foresaw this and, taking an axe, went to the battlefield, supporting Prince Simeon and the Russian army not so much with his presence as with prayer and the call: "Do not be afraid!" As a result, the battle, which seemed lost, ended in victory for the Russians. Since then, Lawrence has been venerated as the savior of the city. In 1515, after his death, the saint was buried in the Church of the Nativity of Christ, where his relics are still considered a source of healing.

Over time, a stone monastery grew at his burial site, which became a favorite place for the people of Kaluga. Destroyed in 1617, it was restored after 1622. From 1776 to 1800, a Spiritual Seminary was located here, followed by an Archiepiscopal residence. By the early 20th century, the monastery had three churches, a bell tower, the building of the former archiepiscopal residence, cells, a fence with towers, and a necropolis.

Many notable citizens and heroes of Russia were buried on the monastery grounds, including Generals K.F. Baggovut and A.M. Vsevolzhsky, participants of the Patriotic War of 1812. In the 18th century, Catherine II visited the monastery, and in the 19th century, N.V. Gogol and members of the royal family. At the end of the 18th century, the Kaluga Diocese was established, and the monastery became an Archiepiscopal residence. After 1917, almost all the buildings of the monastery were destroyed, with only the building of the former archiepiscopal residence remaining. The territory was used as a camp for prisoners, then for a school and housing.

In 1991, the monastery was granted the status of a local natural monument. Three years later, part of the archiepiscopal residence was returned to the Kaluga Diocese, and in 1994, the Archiepiscopal residence, Kaluga St. Lawrence Monastery, was established here.

Today, all remaining buildings have been returned to the monastery, and active restoration work is underway.