On the day of the Nativity of the Virgin Mary in 1380, the Battle of Kulikovo took place, and since then this holiday has gained special significance in Russia. Therefore, shortly after the battle, a monastery was founded in Moscow in honor of the Nativity of the Virgin Mary. The monastery was established in 1386 by Princess Maria Kestutyevna, the wife of Prince Andrei Serpukhovsky and the mother of Prince Vladimir the Brave, a participant in the battle. Later, the princess took monastic vows under the name Martha and was buried in the monastery cemetery in 1389. Due to its location by the Neglinnaya River, the monastery was called 'on the Tube.' Initially wooden, it became stone from the 16th century. Reconstructions continued until the revolution, and now the monastery complex includes buildings from the 16th to the 20th century.

The oldest building, the Cathedral of the Nativity of the Virgin Mary, has a central part that is a cross-domed church with one dome. It was built between 1501 and 1505 and later supplemented with a gallery with chapels and a burial vault for the princes Lobanov-Rostovsky. The western part of the gallery was created in the early 20th century by architect F.O. Shekhtel. Previously, a tented bell tower stood over the right apse of the cathedral, but it was destroyed by lightning in 1835. In 1835-1836, a new four-tiered bell tower with a church on the second tier was built in its place in memory of the son of the church builder. The warm monastery church of John Chrysostom has been known since 1626, but the modern building was erected between 1676 and 1687 with funds from Princess F.I. Lobanova-Rostovskaya. In 1904-1906, a building in the neo-Russian style was constructed against the northern wall of the monastery for a refectory and school. The monastery walls from the 17th century have also been preserved.

In 1525, the wife of Grand Duke Vasily III, Solomonia Saburova, was forcibly tonsured under the name Sophia in the monastery. In 1670, the burial vault of the Lobanov-Rostovskys was built, which later received a second floor. The Lobanov-Rostovsky family has been known since the late 15th century and still exists today.

In the 1920s, the monastery was closed, and its buildings were used for housing and offices. In 1989, the complex was transferred to the Moscow Architectural Institute, but three years later, the process of transferring it to the Orthodox community began. Since 1993, the monastery has been operating again, and restoration work has been carried out, leading to the revival of the cathedral and churches. By 2018, the facades of the churches and burial vault had been restored. The work has been ongoing since 2017 under the supervision of Mosgornasledie. The churches have the status of cultural heritage sites of federal significance. In 2020, the complex became a laureate of the 'Moscow Restoration' competition for the best restoration projects.