One of the architectural gems of Kaluga is the Trading House, built in the late 18th and early 19th centuries on the site of old wooden trading buildings. The initiator of its construction was Mikhail Nikitich Krechetikov, the governor of Kaluga, who did much for the city. He attracted local merchants to the construction, and at a city council meeting, it was decided to gradually demolish the wooden shops so that the merchants would build stone buildings at their own expense according to a unified plan. The project and facade of the future ensemble were approved on May 15, 1782, in St. Petersburg, and construction began two years later.

Initially, the southern buildings were constructed with funds from local merchants by 1788. The shops in the new buildings were allocated among the merchants who participated in the construction. In May of the same year, a group of 12 merchants led by Makar Chernov, dissatisfied with the allocation, submitted a request for permission to build "half a building at their own expense." The city council opposed this, but the provincial administration granted permission, and the first northern building was erected in 1789 next to the Nikitskaya Church. The second northern building was constructed between 1792 and 1794 with city funds. The fifth building was completed no later than 1796 next to the first, facing the end onto Nikitskaya Street.

In 1797, the merchants proposed to reduce the width of the remaining buildings to lower construction costs and improve convenience for trade. However, this required approval from the capital, and construction was halted until 1811. It turned out that the original project had been lost, and Timofey Bogomazov presented a new plan. The final version of the plan, drawn up by Bogomazov and architect Yasnigin in 1812, is kept in the regional museum.

The authorship of the original plan remained unknown for a long time, but in 1960 it was established that it was created by architect Pyotr Romanovich Nikitin. He also worked in other cities, such as Tver and Maloyaroslavets.

Construction of the Trading House resumed with the northern building on Nikitskaya Street, while the merchants were to build the third from the south. However, by the fall of 1813, the southern building had not yet been started. In 1814, the new governor Pyotr Nikitich Kaverin transferred the construction of the next two buildings to the city council, but the process was slow. By 1818, two brick buildings from the previous shops were completed.

In the following two years, under the guidance of architect Yasnigin, four eastern buildings were constructed. In 1821, the Meshkov merchants began building the first of the western buildings. In 1822, Governor Nikita Kuzmich Omelyanenko proposed to complete the construction of the remaining building, but this met with objections from the council. However, the provincial administration insisted on starting construction in 1823, and it was completed by architect Frolov.

As a result of 39 years of work, the Kaluga Trading House was built, one of the oldest in Russia, consisting of 14 buildings. The buildings are connected by arches decorated with columns and Gothic elements. The southern buildings have a semi-basement floor, adorned with an arcade of massive columns and a parapet with Gothic towers. The northern buildings resemble the southern ones but lack the semi-basement floor. The western buildings feature a gallery of twelve columns, while the eastern ones are decorated with half-columns and arches.

After the construction was completed, part of the premises was used for public needs. In 1847, a public library was opened in the second eastern building, which resumed operations in 1888. The remaining premises belonged to merchants and changed hands. By the end of the 19th century, the building had deteriorated, and the owners began making changes to the architecture, leading to a loss of its historical appearance. In 1910, merchant Komarov wanted to change the facade of the building in the Art Nouveau style, but public intervention prevented this.

In 1960, the Trading House was recognized as an object of cultural heritage of federal significance. In the 1970s, department stores were placed in the two southern buildings. In 1976, the area of Stary Torg was raised, and the semi-basement floor of the southern buildings went underground.

Currently, the buildings are managed by private tenants who are responsible for their maintenance. In 2009, the Trading House was transferred to regional ownership, and in 2010, restoration began, completed by 2015. A project to cover the inner courtyard with a dome is being discussed, but no decision has been made yet.