The Vvedensky Women's Monastery in Oryol was founded in 1685 at the Vvedenskaya Church in the city center. After a fire in 1843, it was relocated to the Christ-Redeemer Church on the southern outskirts of the city, beyond the Oka River, and opened at the new site in 1848. In the 1850s, a fence with towers was built, and the second half of the 19th century was marked by the construction of monastic cells. By 1917, the monastery was populous, but it was closed in 1923, and the buildings were repurposed for housing. The restoration of the monastery began in 1995.

The monastery was founded in 1686 on the site of the burned church of Saints Athanasius and Cyril of Alexandria. The main church was consecrated in the name of the Entry of the Most Holy Theotokos into the Temple, which gave the monastery its name. In 1769-1770, the Tikhvin Church was built above the gates.

From 1821 to 1845, the monastery was managed by Schema-Hegumen Seraphima (Sokovnina), known for her piety and strict lifestyle. She became an example for the nuns of the monastery and attracted the attention of Empress Alexandra, who visited her in 1837. Documents about her life have been submitted to the Synodal Commission for the Canonization of Saints.

In the first third of the 19th century, the monastery was surrounded by stone walls with towers. In the center stood the stone Vvedenskaya Church with a bell tower, and above the holy gates rose the Tikhvin Church. There were about 75 wooden cells on the territory. Thanks to donations and support from the residents of Oryol, the monastery became a decoration of the city by the end of the 1830s.

The fire of 1843 completely destroyed the monastery, leaving 200 nuns homeless. The townspeople mourned the loss, and the sisters refused to leave the monastery, awaiting its restoration. In 1844, a new site for the monastery was chosen outside the city, near the Christ-Redeemer Church. In 1848, the monastery was solemnly opened at the new location.

In 1865, the gate church in honor of the Tikhvin Icon of the Mother of God was completed. In the 1860s, the monastery continued to develop, and the number of cells again reached 75. In 1870, a wooden refectory building was constructed, as well as a hospital, almshouse, and a school for girls. In 1885, a burial church in honor of the Resurrection of Christ was built, and in 1887, a church in the name of the Life-Giving Trinity was consecrated.

By the beginning of the 20th century, the monastery was fully equipped and considered the best monastery in the Oryol Diocese. In 1901, it housed 583 nuns. Many notable figures visited the monastery, including empresses and Saint John of Kronstadt.

In 1923, the monastery was closed, and many of its nuns faced repression. In 1937, over a hundred former nuns were arrested and sent to camps. In 1949, the territory of the monastery housed the Coopremont artel, and from 1965, the Oryol Rubber Technical Products Plant.

By the early 1990s, the buildings of the school and 37 cells remained on the monastery grounds. In 1993, the restoration of the monastery began, and in 1994, the Tikhvin gate church was consecrated. In 1995, the first tonsure took place, and the gradual restoration of churches and buildings began. Today, several churches have been restored, and new buildings for the sisters and pilgrims have been constructed. The monastery has a library, a Sunday school, and workshops. There are 26 nuns living in the monastery.