This article generalizes and systematises the experience of studying mediaeval caravanserais in Karasubazar, with the ruined site of one structure located on the territory of the modern city of Belogorsk (Republic of the Crimea). Various groups of historical sources have been used, with considerable attention to the journals of numerous travellers who visited the Crimean Peninsula (P. S. Pallas, P. I. Sumarokov, F. Dubois de Montpereux, A. N. Demidov, etc.). The earliest travelogue was written by Evliya Celebi. This Ottoman traveller observed the largest khan in the town (hereinafter referred to as the Upper Tash-khan, or Sefer Gazi-aga’s caravanserai) shortly after its significant reconstruction and strengthening, which was probably made with the view of the need to strengthen the defences of the town and its residents in the view of regular devastating raids of the Cossacks in the 1620–1630s. The widely used graphic sources, particularly the works by C. Bossoli made in the early 1840s, indicate that the buildings in question were abandoned and lost their former function. The analysis has been made of the works of K. F. Bogaevskii, whose sketches of Crimean antiquities made under the order from the KrymOKhRIS (Section / Sub-department / Committee for the Protection of the Monuments of Art, Antiquity, and People’s daily Life in the Crimea) reflected the preservation of the monuments in the mid-1920s with photographic accuracy. Pencil sketches by U. A. Bodaninskii have been used as well. A set of photographs from the collections of the Bakhchisarai Historical and Cultural Archaeological Museum Preserve, A. V. Shchusev State Scientific Research Museum of Architecture (Moscow), and Central Museum of Taurida (Simferopol) allowed the ones to reconstruct the appearance of the site in the 1920–1930s. The participation of academic institutions in the study of cultural heritage sites of Karasubazar in the first half of the twentieth century has been analysed, and the activities of the Central State Restoration Workshops which sent the architect B. N. Zasypkin to the Crimea have been considered. The main stages of the creation and functioning of the trading khans in the town under study have been characterized, and the architectural analysis has been done.