In the 18th century, the site of the modern Trading House was occupied by numerous wooden shops arranged chaotically. The idea of building a trading house with worthy architecture emerged from Governor M. N. Krechetikov shortly after his appointment in Kaluga. He proposed that local merchants finance the construction, and the city council decided to gradually demolish the wooden shops so that the merchants could erect stone buildings according to a unified plan.

The plan and facade of the future ensemble were approved in the capital, but later the plan was lost, and for a long time its author remained unknown. In 1960, T. M. Syitina suggested that the architect was P. R. Nikitin, who developed the city planning in 1776.

The first order for the construction of the trading house dates back to April 24 (May 5) 1782. Construction began with two southern buildings, and by 1788 they were erected at the expense of the merchants. In May of the same year, a group of merchants dissatisfied with the distribution of shops received permission to build a building at their own expense. The first northern building was constructed in 1789, and the second between 1792 and 1794. The fifth building was completed by 1796.

In 1797, the merchants proposed to change the project by reducing the width of the buildings to lower construction costs and improve trading conditions. However, the changes required approval from the capital, and construction was halted until 1811. The original project was lost, and a new plan was presented by Timofey Bogomazov in 1811. Construction resumed, but due to delays and disputes between the merchants and authorities, it progressed slowly.

By 1820, under the guidance of I. D. Yasnigin, the remaining buildings were constructed. In 1821, construction of the western buildings began, and by 1823, it was completed under the direction of architect N. F. Sokolov.

After the collapse of the USSR, the buildings were transferred to private tenants who were responsible for their maintenance. In 2009, the Trading House was transferred to regional ownership, and in 2010, its restoration began, which was completed by 2015. A tourist and recreational zone was planned.

In 2018, a project to cover the inner courtyard with a dome was discussed. By 2020, the Trading House housed restaurants, a museum, a barbershop, a visitor center, and other organizations, as well as the opening of the Small Hall of the Regional Philharmonic.