The exact date and circumstances of its founding remain unknown, but legends attribute its appearance to the 13th century, possibly during the reign of Prince Roman of Uglich. Initially, it was located on the banks of the Volga, near the mouth of the Trinity stream. It is first mentioned in documents from the second half of the 15th century, when Archimandrite Nafanail, a contemporary of Uglich Prince Andrei the Great, attended the consecration of the Protection Cathedral at the namesake Uglich monastery in 1482. The archimandrite's authority remained in the monastery until its closure in 1764. By the decree of Prince Dmitry Zhilka in 1509, the monastery was granted the village of Sintsovo with its hamlets and the village of Olifnnikovo. In 1609, the monastery was captured by the Poles, resulting in the deaths of Archimandrite Lavrenty, about 60 monks, and around 500 defenders of the monastery.

According to sources, in the 1670s, only wooden structures were present on the monastery grounds, including the cathedral Resurrection Church, the Church of the Smolensk Mother of God Odigitriya with a refectory, the gate church of Mary of Egypt, a tented bell tower, residential and utility buildings, as well as a fence. Between 1674 and 1677, by the order of the Rostov Metropolitan Ionas Sysoevich, a stone ensemble of the Resurrection Monastery was built at a new site known as "Luzhitsy," representing an outstanding example of Rostov architecture from the second half of the 17th century. The complex consists of three buildings arranged in a line and connected by a gallery. On the northern side stands the large Resurrection Cathedral with two chapels: the northern in honor of Archangel Michael and the southern in honor of Jacob. Next is a three-arch bell tower with an altar of Mary of Egypt. The ensemble is completed by the refectory and the Church of the Smolensk Mother of God. Above the refectory is a clock tower. The walls are adorned with glazed tiles. It is possible that the construction was overseen by the "stonework apprentice" I. Sakuyain, while the frescoes were executed by Kostroma icon painters under the guidance of Ionin, with only a few small fragments remaining.

In 1764, the monastery was abolished and transformed into a parish church, with Hieromonk Philotheus as its rector. Icons, utensils, and church items were transferred to the Uglich Alexeyevsky Monastery and later partially returned for the parish church's arrangement. The altar of Mary of Egypt was abolished, and the names of the chapels of the Resurrection Cathedral were changed: the northern became in honor of the Vladimir Mother of God, and the southern, Znamensky. In 1777-1778, a commission from the spiritual consistory inspected the condition of the stone buildings and recommended urgent repairs. The wooden structures were also in a state of disrepair. From the 1780s, the refectory housed the district spiritual school. In the early 19th century, restoration work began, including roof repairs, strengthening of the walls and vaults of the cathedral, and restoration of the fence. By 1811, the brick gates were fully restored. From 1814, the restoration of the decorative painting in the Vladimir and Znamensky chapels of the cathedral began. In 1851, artist A.I. Nenastev painted the dome of the Resurrection Cathedral, and in 1862-1865, D.G. Burenin repainted the walls of the church. Fragments of the frescoes have survived to this day. Despite intensive work in the early 20th century, the ensemble found itself in a state of emergency due to weak soil.

In 1918, the monastery was transferred to the Uglich Museum of Antiquities, where part of the collection of ancient Russian art was temporarily housed. In the 1920s, the basement premises were used as warehouses. In the mid-1930s, the monastery fell within the construction zone of the Uglich Hydroelectric Power Station and was used for the needs of "Volgostroy" of the NKVD. In the 1950s-1970s, a comprehensive restoration was carried out, including chemical soil stabilization, which saved the monument from destruction. In the late 1980s, the museification of the monastery began but was halted due to a lack of funds.

In the spring of 1999, thanks to the efforts of the late Archbishop of Yaroslavl and Rostov, Mikhail, the complex of buildings was transferred to the Russian Orthodox Church, and a men's monastery was revived there. The first abbot was igumen, now Archimandrite Viktor Zakharov. On June 6, 2000, the first Divine Liturgy was held, and on September 18 of the same year, the Church of the Smolensk Icon of the Mother of God was consecrated by Bishop Joseph.