The convent was founded in 1390 by Grand Prince Oleg Ivanovich of Ryazan on a high bank of the Staritsa River, where it merges with the Solotcha River. For a long time, it served as the northern outpost of Pereyaslavl-Ryazansky. According to legend, the prince decided to establish the convent after meeting two hermits, Vasily and Euphemia, on the banks of the Solotcha. Oleg of Ryazan cared for the convent until the end of his days, took monastic vows there, and was buried. His son Fyodor Olgovich, grandson Ivan Fyodorovich, and other Ryazan princes and princesses generously donated to the development of the convent. In the early 15th century, Salahmir, an ancestor of the noble Ryazan families of Verderievsky, Apraksin, and Duvanov, was buried here. In 1552, the troops of Ivan the Terrible stopped at the convent on their way to Kazan. In 1618, the convent was attacked by the troops of Polish prince Vladislav and hetman Pyotr Sagaidachny. A new flourishing of the monastery occurred in the late 17th century thanks to Archimandrite Ignatius Shangin, under whom the convent acquired its modern appearance. In 1764, during the secularization reform of Catherine II, the convent was classified as second class. In 1768, the Oka River eroded the bank, causing part of the walls along with the Protection Church to collapse. On May 12, 1827, Ilariy Irodionov became the archimandrite, who significantly enriched and improved the convent over seven years. In 1917, the convent was closed by the Soviet authorities and used as a colony for minors. Later, the architectural complex became part of the Ryazan Historical and Architectural Museum-Reserve, and in the 1960s, restoration of the buildings began.

The first church of the convent was a wooden Protection Church, where Prince Oleg Ivanovich of Ryazan and his wife Euphrosinia were buried. In the mid-16th century, a stone church dedicated to St. Alexius, Metropolitan of Moscow, was built in honor of Ivan the Terrible's campaign against Kazan. However, these buildings have not survived: the Protection Church was lost in the late 18th century due to the bank collapse, and the church of St. Alexius was dismantled in the 19th century due to its dilapidation. Three churches of the convent have survived to this day: the gate church of John the Baptist from 1695, built during Archimandrite Ignatius Shangin, and the Holy Spirit Church with the refectory from 1688 and 1689. These structures in the Naryshkin Baroque style were likely created according to the design of architect Yakov Bukhvostov. The territory of the convent also includes the 17th-century Abbot's House, the five-domed Nativity Cathedral from 1691, and the fortress walls from 1688. Stepan Polubes worked on the tile decorations of the gate church, known for his works in the New Jerusalem and Joseph-Volokolamsk monasteries.