By the First World War, three decades and a half after the end of Ottoman rule, Sofia had largely received its physiognomy as the modern capital of a European nation-state. The combined efforts of foreign engineers and architects and, by the turn of the century, a young cohort of Bulgarian professionals with Western education, under the strict control and guidance of the central state authorities, had resulted in a new city plan combining the radial and the grid systems, and an architectural profile in line with contemporary European models. Against this background, national historiography has interpreted Ottoman rule as a destructive regime imposed by a conqueror who carried a backward, if any, understanding of urbanism. The five centuries of foreign yoke were a period of stagnancy for the city and its infrastructures, a time when the urban substance degraded and succumbed to an elementary mode of living and mediocre building practices. This paper problematizes the dominance of the grand narratives of rapid modernization and de-Ottomanization elaborated in the Ottoman successor states as the legitimate framework for the study of modernity. Focusing on Sofia as one of the stereotypical examples of rapid de-Ottomanization, my research addresses the city’s transformation from an Ottoman provincial center to the modern capital of a nation state in the aftermath of empire. While the level of reconfiguration of urban space in Sofia in the decades following the Russo-Turkish war of 1878-79 was indeed exceptional, some of the main directions in the transformation of the urban fabric had already been charted in the Ottoman period. One example is the regularization of the street network and the efforts taken towards straightening and widening of the main streets, a process initiated by the Ottoman authorities already in the 1860s. My research, furthermore, points at a remarkable degree of continuity in the use and management of the city’s water supply network, an area that was otherwise at the forefront of the modernization project. Tracing the roots of urban transformation in the Balkans to the Ottoman period, and stressing the porous nature of the boundary between empire and nation-state, my analysis ultimately seeks to re-focus the modernity discourse on a three-dimensional system with Western, Ottoman, and Bulgarian actors.