The Holy Assumption Likhvinsky Gremyachev Men's Monastery was founded in the 16th century. This is evidenced by documents from the Kaluga Diocese, where the first abbot, Macarius, is mentioned in 1584. The monastery was abolished in 1764.

Tsar Alexei Mikhailovich, on his pilgrimage to Kyiv, stopped at Gremyachev Monastery. He was struck by the beauty of this place, and on the monastery hill known as "Conversation," the Holy Virgin is said to have appeared to the Tsar and conversed with him for a long time. Soon, the Tsar allocated funds for the construction of a large stone Cathedral in honor of the Assumption of the Mother of God.

The five-domed Assumption Cathedral was built and consecrated in the 1680s. The church in honor of St. George the Victorious was erected 20 years later. This is confirmed by a plaque with an inscription installed on the western wall, "in 1701 by the efforts of the hieromonk cellarer and the brotherhood." Later, a fence made of local limestone and shell rock was built around the monastery, which is a monument of 18th-century architecture.

Initially, an open gallery adjoined the Assumption Cathedral, and on the southern side, there was a wooden bell tower with a 15-pud bell, cast in 1674 by the efforts of the abbot Cornelius and the brotherhood. By the early 19th century, the bell tower had fallen into disrepair and was replaced with a new one in the classical style. Previously, a brick kitchen adjoined the western part of the refectory, which was later dismantled for the construction of the bell tower.

The monastery was not wealthy; in 1700 it had 36 peasant households with 303 men and 80 desyatinas of land. In 1724, it was annexed to the Dobro Monastery, but in 1727 it became independent again. Under Catherine II, the monastery was abolished in 1764 when spiritual states were established. The churches became parish churches, and the land within the fence turned into a necropolis.

The revolution had little effect on the monastery churches, and services continued until 1935 when the churches in Gremyachevo were closed. Local residents dismantled the church icons for their homes. In the 1990s, when services resumed, one icon returned to the monastery, and the icon of the Assumption of the Holy Virgin was transferred to the Moscow Church of Elijah on Obidenka.

From 1962 to 1988, the churches were used by the collective farm "Red October" for storing spare parts and fertilizers. Tractors entering the territory completely destroyed the ancient necropolis. However, the memory of the appearance of the Mother of God and the miracles that occurred here remained. Local residents tell of the apparitions of the Holy Virgin and the wonderful singing. In the year of the Millennium of the Baptism of Rus, they appealed for the resumption of services in the Church of St. George. In 1989, a priest, George (Zinovyev), was sent to Gremyachevo, who served for about 20 years and was buried at the altar of the Church of St. George the Victorious.

In 2008, with the blessing of Metropolitan Clement of Kaluga and Borovsk, four sisters from the Holy Nicholas Chernoostrov Women's Monastery in Maloyaroslavets moved to the monastery to restore the shrine and renew monastic life, and Gremyachev Monastery became a dependency of the Maloyaroslavl Monastery.

The monastery is currently active. Daily services are held in the churches, the number of residents is increasing, and forms of social service are being improved. The sisters care for children from the North Ageev Special Boarding School for Orphans and Children without Parental Care.