This is one of the oldest squares that emerged in Podil during the time of Kyivan Rus. After the center of Kyiv was moved to Podil due to the destruction of the Upper Town by the Mongol-Tatars, Kontraktova became the main square of the city. In the 15th century, the town hall was built here, and in the 18th century, this place became the center of international contract fairs. The square acquired its modern appearance at the beginning of the 19th century. Then, the Guest House, the new Kontraktova House, was built here.