The Church of Saints Cosmas and Damian is one of the oldest temples in Kaluga. It was founded several decades before Napoleon's invasion. According to most local historians and art experts, the plan for the church's construction emerged in the late 1770s. At that time, Mikhail Nikitich Krechetikov, the famous Kaluga governor, took office as the governor-general of the Kaluga and Tula provinces and began the city's reconstruction. Significant architectural monuments were built then, including the Church of the Savior Not Made by Hands, completed in 1794. This church, built in the Baroque style, became one of the most beautiful.

In 1828, two altars were added to the Church of the Savior Not Made by Hands: in honor of Cosmas and Damian and Saint Nicholas, under whose names it entered history. In 1886, iconostases were installed in the altars. After the Bolsheviks came to power, the church faced severe persecution. In 1926, Hieromonk Antoniy Kobeleva and Priest Nikolai Vylezhinskiy, who served in the church, were arrested for "anti-Soviet agitation" and sent into exile. In 1937, the church was closed, and for some time it was used to house prisoners, leading to its appalling condition.

In the post-war years, the closed church building housed a garage and utility warehouses. In 1960, the church was declared a monument of architecture and urban planning of republican significance, but it continued to be used as a warehouse. The building was returned to the Kaluga Diocese only on July 17, 1992. Initially, restoration of the church was undertaken by Archpriest Nikolai Sukhodolov, followed by Georgiy Gafarov. The consecration of the central altar was conducted by Archbishop Kliment on August 27, 1998, after which regular services began, although repairs are still not completed. Since 1999, two Sunday schools have been operating at the church: for children and adults.

Today, the external architecture of the church stands out among other churches in Kaluga for its elegance and proportionality. The volumetric-spatial structure and decorative finishing of the facades alternate between classical and Baroque motifs. In plan, the church resembles a ship with a petal-shaped base. The main volume is built with four connected semicircles. The high domed vault is topped with five domes on light drums. The side entrances are adorned with tall portals featuring two pairs of slender columns, above which are more elegant columns supporting pediments. The window frames and other details are characterized by massiveness and expressiveness. The four-tiered bell tower and large refectory are executed in the strict forms of early classicism. The bell tower gradually narrows towards the top and originally stood separately from the church but was connected to it by a porch in the 19th century. The apse is characteristic of cult buildings from the mid-18th century. The side domes of the church are the fourth tier of the exedras adjoining the church. The composition of the five domes resembles churches built by the famous Rastrelli, suggesting that the architect was someone from his students. This assumption is quite plausible, considering the interest of the capital's authorities in Kaluga after the establishment of the Kaluga and Tula provinces and the appointment of Mikhail Nikitich Krechetikov as governor.