The Church of the Annunciation of the Blessed Virgin Mary above the Holy Gates of the Spaso-Evfimiev Monastery was considered one of the main adornments of the monastery in the 17th century. However, it receives little attention in literature, possibly due to its current modest appearance. One source from the 19th century mentions that this is a single-domed church where services are held rarely, as it is accessed by a steep staircase, and the church is cold, without stoves. It is also claimed that the church is not ancient, as it is not mentioned in the inventory of 1660.

These details, while containing important information, distort the perception of the Annunciation Church. The first mention of it appears in the inventory of 1628-1630, which speaks of a stone church of the Annunciation and the chapel of John the Ladder. This information does not provide exact data about its appearance or date of construction, which remains a contentious issue. It is assumed that the church may have been built between the late 16th century and 1653. Stone multi-domed churches, to which it belongs, are known from the 1620s-1630s. For example, the Church of the Assumption of the Blessed Virgin Mary in Uglich and the Cathedral of the Alexeyevsky Monastery.

Initially, the Annunciation Church harmonized with the monastery towers and the refectory Assumption Church. However, in the second half of the 17th century, its appearance changed. The similarity in composition and decor suggests that it was rebuilt by the same group of craftsmen who constructed the stone walls and the hospital church of St. Nicholas. By the mid-18th century, the church acquired its modern appearance. The inventory of 1722 mentions a stone church with five domes covered with tiles. In 1764, further changes were recorded: a wooden octagon and a painted dome. Later, the octagon was replaced with a flat ceiling, and the chapel of John the Ladder likely became part of the refectory of the Assumption Church.

Today, the Annunciation Church is a small cube above one of the openings of the Holy Gates. To the east, it has a high three-part apse, and to the west, a porch under a wooden roof. The decor made of shaped bricks is diverse and characteristic of the mid to late 17th century. Key elements include shaped window frames, the apse, and the porch, as well as the icon case of the Savior. A wide carved cornice runs above the windows, reminiscent of the decoration of the older bell tower church of the Nativity of John the Baptist. It is possible that the frieze separates the ancient masonry from later changes, and the upper belt is adorned with decorative kokoshniks and panels.