The Church of John Climacus, built in 1572 with funds from the sons of Ivan the Terrible, princes Ivan and Fyodor, has a main altar and an aisle dedicated to the saints John Climacus and Fyodor Stratilates. The church stands out for its exterior appearance and ornate decoration. The cubic shape of the building, divided by pilasters into three parts, is topped with semicircular zakomaras. In the 18th century, a four-pitched roof was added, concealing two tiers of kokoshniks that previously served as a transition to the light drum of the dome. The shift of the drum to the eastern side gives the composition a slight asymmetry, which was previously enhanced by a small dome on the southeast corner. Such double domes are rarely found in ancient Russian architecture, although they are quite common in Kirillov and Ferapontov. The entrance to the church is located on the western side through a covered porch connected to the lower floor by a staircase in the southern wall. Initially, the porch had open arched openings, which were later replaced by windows, but the pilasters from the arcade have been preserved. A beautiful portal with columns decorated with melons and a keel-shaped top leads to the porch.

The interior of the church is also unique. The barrel vaults with arches supporting the dome drum rest on four pillars. The eastern pillars are traditional, quadrangular, connected by a wall separating the altar, while the western ones are round, designed as columns with bases and capitals. The bases of the vaults are marked by impost cornices. The western part of the central nave is covered with cross vaults, which is an example of 'Italianisms' introduced to Russia by foreign architects during the reigns of Ivan III and Vasily III. The apse of the church is low and rectangular, characteristic of gate and refectory churches of the 16th century, with niches-arcossoliums and a stone bench along the walls. In the southeast corner is the chapel of Fyodor Stratilates with a rectangular altar section and a four-tiered iconostasis, which retains icons from the 16th-17th centuries. Two icons not included in the iconostasis are placed on the walls. The royal gates from the 16th-17th centuries stand out with carvings in the form of a woven pattern, reflecting the folk northern ornamentation.