Introduction: This paper analyzes the formation and development of major medieval settlements that emerged in the 14th–16th century within the boundaries of the modern Bakhchysarai. We studied written and archaeological sources to examine the evolution and structure of these settlements, and provide a general overview of the surviving architectural ensembles and landmarks. Bakhchysarai, the former capital of the Crimean Khanate, is one of those Crimean settlements where the medieval planning structure of the old town and the original organic links to the natural landscape survive to this day. Purpose of the study: We aimed to identify the historical background and specifics of how the Old Town and the surrounding historical complexes formed in Bakhchysarai. Our research involved examining historical, archaeological, and contemporary scientific sources and written media, as well as selecting and analyzing theoretical works, normative documents, and architectural designs relevant to the subject at hand. When making a systemic summary of the data that we examined, we used the following methods: structural and functional analysis, synthesis, deduction, generalization, and the comparative historical method. Results: Our findings show that, at the early stages of statehood in the Crimean Khanate, several settlements thrived in the region: Eski Yurt, which started out as a cultural, administrative, and economic hub and eventually became a major religious center; Qırq Yer, an ancient fortified cave settlement that survived into the early 20th century; and the Salacık settlement at the foot of Çufut Qale, which became the most direct precursor of the new capital in Bakhchysarai. The ruins of these settlements are part of the modern Bakhchysarai’s cultural heritage; they lie within its boundaries and greatly influence its modern appearance.