In the late 14th century brother Savva founded a new monastery on the Storozha Hill, one of the oldest in the Moscow Region.
The first buildings of the Monastery were made of wood. On the Storozha Hill the brethren erected the Church of the Nativity of the Virgin and some cells. Prince Yuri, second son of Grand Duke Dmitri Donskoi, actively patronized the new establishment, granting it gold, villages with their grounds, exemption from taxes and duties for all those living on the monastery's lands.
In 1404-05 the wooden cathedral is replaced by one made of white stone, dedicated to the Feast of the Nativity of the Virgin. The stone altar was created in the 15th century.
In the early 17th century, during the Polish-Lithuanian invasion, the monastery was severely damaged. After the invasion, the monastery was restored and began to play an important role in the development of the Russian statehood. Beginning with the epoch of the first tsars of the Romanov Dynasty it was unique in combining the functions of a royal residence and a place of pilgrimage.