According to legend, the monastery was founded in 1288 by the Bryansk prince Roman Mikhailovich. The legend tells that the prince began to lose his sight and sent messengers to the Kyiv-Pechersk Monastery for a miraculous icon of the Mother of God. On the way along the Desna River, the icon disappeared from the boat and appeared on the bank of the Svyen River, where the prince arrived. After praying before the icon, he was healed and ordered the construction of a monastery and church in honor of the Mother of God at that place, as well as endowed it with lands. Until the 17th century, the monastery was called Svinsky after the Svyn River.

Documentary mentions of the monastery appear in the 16th century when Ivan the Terrible ordered the construction of two stone churches here, including the church of Saints Anthony and Theodosius of the Caves, restored in 2011. In 1583, the monastery was destroyed by the Lithuanians, and in 1664, by the Crimean Tatars.

The architectural ensemble of the monastery is executed in the style of Sloboda Baroque. In 1679, the gate church of Sretenie was built, which has survived to this day. According to church legend, Peter I visited the monastery. The house where he allegedly stayed existed until the early 20th century, and the "oak of Peter the Great" still stands in front of the monastery, being a well-known landmark.

In 1681 and 1786, the monastery was assigned to the Kyiv-Pechersk Lavra and was called Novo-Pechersk. During this period, the gate church of Spaso-Preobrazhensky (1742) and the Uspensky Cathedral (1758, demolished in 1930) were built. One of the largest fairs in western Russia took place in front of the monastery.

After the monastery regained its status as independent, it was renamed Svensky, and the Svyn River became known as Svyen. According to the Manifesto on the secularization of monastery lands (1764), the monastery was classified as third class.

The Svensk (Pechersk) icon of the Mother of God was taken to Moscow to the Tretyakov Gallery after the October Revolution. It is traditionally attributed to the Kyiv-Pechersk icon painter Alipiy (11th century).

In the 1920s, the closure of the monastery began, which was completed by 1926. In 1930, a significant part of the buildings, including the main cathedral, was demolished. The Uspensky Cathedral was blown up, damaging the church of Saints Anthony and Theodosius of the Caves, of which only the lower tier remains.

In 1992, the remaining buildings were returned to the church, and the monastery was revived. As of 2014, the restoration of the architectural complex continues, including the blown-up cathedral.

Today, the monastery is active, with daily services held in its churches. The number of residents of the monastery is growing, and forms of social service are being improved.