The foundation of the monastery dates back to the late 16th century, although the exact date is unknown. Initially, it existed as a women's community at the parish church of the Nativity of Christ and was mentioned in sources as the Nativity or Ioanno-Predtechensky. The wooden Nativity church and the later built brick temple have not survived. The monastery did not have its own land and lived modestly on state subsidies and donations. The city of Sviyazhsk and the monastery buildings repeatedly suffered from fires. After the fire in 1795, which destroyed the monastery buildings, it was given the vacant structures of the former men's monastery. This marked the beginning of a new phase in its history, when the community flourished thanks to significant state support. New brick utility and residential buildings appeared in the monastery. In 1796, the Ioanno-Predtechensky chapel and bell tower were added to the Sergievskaya church.

From 1898 to 1906, architect F. N. Malinovsky built a large cathedral in the Neo-Byzantine style in honor of the icon of the Mother of God "Joy of All Who Sorrow." Every year, starting from Thomas Sunday, this icon was carried in a procession through the towns and villages of the Kazan diocese. The tall cathedral building, located on a hill, became the architectural dominant of the city. By the early 20th century, the monastery had up to 400 nuns and novices, making it the second largest women's monastery in the diocese after the Kazan Mother of God.

The monastery was closed in 1919. During the Soviet era, all churches came under the jurisdiction of the Sviyazhsk Historical and Architectural Museum-Reserve. The ancient iconostasis of the wooden Trinity church was transferred to the State Museum of Fine Arts of the Republic of Tatarstan. The church itself was restored in 1959. The interior decoration of the large cathedral has been preserved. The building of the Sergievskaya church was studied by Kazan art historians such as G. P. Rylova, V. V. Malkovskaya, and S. S. Aydarov.

Currently, two of the three churches, except for the Trinity church, have been transferred to the Assumption Monastery.

The architectural ensemble of the monastery has been preserved quite well. It includes both structures remaining from the Trinity-Sergius Monastery and buildings from the 19th and early 20th centuries.

The oldest church not only in the monastery but also in the entire Middle and Lower Volga region, the wooden Trinity church of 1551, is the only monument remaining from the original wooden Sviyazhsk. It has unique cultural and historical value as one of the oldest wooden churches in Russia. However, its appearance has partially changed during the reconstructions of the 19th century: the church ceased to be tent-like, received a new iron roof and dome, as well as a shingle covering. The interior was significantly altered during the Soviet era, with icons from the 16th and 17th centuries removed, but the structure of the carved iconostasis has been preserved.

The second oldest church of the monastery, a stone one, is dedicated to St. Sergius of Radonezh and dates back to 1604. It is a single-domed church with a low bell tower added a little later. Inside, it represents a rare type of single-column refectory church. On the covered porch, to the right of the entrance, there is a large fresco depicting the "Old Testament Trinity" with images of Saints Sergius of Radonezh and Alexander of Svir. The fresco is contemporary with the church and attracts great interest from art historians, being an exact but enlarged copy of Andrei Rublev's "Trinity."

The third church, the cathedral in honor of the icon of the Mother of God "Joy of All Who Sorrow," is the largest and latest structure in Sviyazhsk, a monumental, multi-domed building in the Russian-Byzantine style.

The bell tower-chapel from 1901, now consecrated in honor of the Holy Royal Martyrs, and a number of residential and utility buildings of the monastery from the 1820s, 30s, and 1890s have also been preserved.