Although a growing body of literature examines the post-socialist European context of urban regeneration, studies on the demolition-based approaches are relatively scarce. Moreover, the regeneration policies of cities in non-EU Balkan countries with a distinctive transitional path remain largely unexplored. The paper contributes to filling these voids by investigating a specific demolition-based urban regeneration strategy named permanent reconstruction, which has been launched in Novi Sad, Serbia’s second largest city, and applied to low-density neighborhoods with a derelict housing stock, being seen as a tool for achieving sustainable urban development. The specific research aims are to explain the origin of this strategy; analyze the institutional and planning framework, mechanisms, and dynamics of the regeneration process through a case study; and assess its outcomes based on a mixed methodology. The main research objective is to identify the issues of a post-socialist entrepreneurial urban governance, primarily deriving from Serbia’s distorted transition, which hampered the development of a strategic, integrated, and locale-conscious approach. The findings suggest that Novi Sad and other Serbian cities necessitate socially responsible and context-perceptive regeneration that would produce sustainable regeneration projects. The authors propose the means for redefining them, emphasizing the responsibilities of the public sector and the significance of involving the local community in the planning and decision-making process.