The Monastery was initially founded in 1370 on a land that belonged to the boyar Simeon Khovrin, who took vows under the name Simon (hence the name of the monastery). It was meant to be a part of Moscow’s defense.
Around 1380, the monastery was moved to its current location. In 1405 the Assumption Cathedral was added. In 1640 it was heavily fortified so as to fulfill its defense purposes.
Shut down in 1923, most of its buildings were destroyed so as to build the ZILA Culture Palace. Nowadays the only remnants of the monastery are a part of the wall and three towers.