Vysotsky Monastery was founded in 1374 by Prince Vladimir Andreevich the Brave of Serpukhov with the blessing of St Sergius (Sergi) of Radonezh. Much of the monastery was destroyed in Crimean raids in 1571 and subsequently rebuilt. During the Soviet period the monastery was closed and even at one point used as a barracks. Now the monastery has been returned to its former glory surrounded by large white walls and is once again a functioning monastery. The monastery has a revered copy of the Inexhaustible Chalice Icon, which is said to help cure alcoholism. It is not permitted to take photos on the territory of the monastery and this policy is usually strictly enforced for some reason!

The monastery's main entrance is next to the Bell Tower which includes the Three Holy Hierarch's Church. After this is the Intercession Church which was first built in the 16th century but has been rebuilt several times since. The monastery's main cathedral is the Conception of Anna Cathedral which stands in the centre and has five large blue domes. It dates from the 16-17th centuries when it was built to replace the original 14th century cathedral destroyed by the Crimean Tatars. Behind the cathedral is a small graveyard and then the All Saints Church which stands against the monastery wall.  It was built in the late-19th century by a local fabricant to serve as a family crypt. Finally in the south-east corner is the Inexhaustible Chalice Icon Church.