This contribution discusses changes among the typical settlements of the Balkans during the 15th century when Ottomans ruled the region. The land was scattered with mountaintop castles of powerful feudal lords, large land-owning monasteries, and peasants living in feudal servitude. Towns with an urban structure, hosting a population living from crafts and trade, and a proper administration mushroomed all over the region. This change is studied through the example of the city Stolac (pronunciation: Stolats) in Bosnia-Herzegovina. It shows the alteration of the medieval settlements from a hamlet to an Ottoman town and Islamic cultural centre. The study analyses historical and demographical data, in combination with the architectural heritage of Stolac, benefiting from rich archival material published by the author, fed by travellers' description and fieldwork results. The case study of Stolac supports the discussion and related theories about the emergence of towns across the Balkans at the arrival of Ottomans.