According to legend, the Svyato-Lavrentiev Monastery was founded in 1515 by Prince Simeon of Kaluga. It was established around a wooden church dedicated to the Resurrection where St Laurentius (Lavrenti) of Kaluga had been buried. St Laurentius was a holy fool who was known for walking around barefooted and in light clothing all year round. He is credited with saving the city in 1512 when he warned the prince of an approaching Crimean Tatar army. During the Times of Troubles the Second False Dmitri sought shelter here and the monastery was virtually destroyed in subsequent battles. Afterwards the monastery was restored and more stone construction work took place in the 18th and 19th centuries.

By the 20th century the monastery had three churches. In 1918 the monastery was closed and later used as a forced labour camp. The monastery's churches were knocked down in 1929. In 1993 a wooden cross was erected over the supposed burial site of St Laurentius and the territory and buildings were returned to the Kaluga Eparchy in 1994, which re-established the monastery. The monastery's churches are now in the process of being rebuilt. The Resurrection of Christ Cathedral is being rebuilt incorporating the foundations of the 1650 version. St Sergius of Radonezh's Church was consecrated in 1994.