Areas of disused military barracks are commonly exploited as a land resource that is attractive for redevelopment, within the urban city area. Their commercial potential is high on the list of attractiveness, primarily based on the value of the site?s disposition, size, and capacity for redevelopment in terms of rebuilding. Contemporary architectural practice is often directed towards urban redevelopment projects in military areas whose position and other characteristics are valued by investors as crucial commercial benefits. These sites may be places of tangible cultural heritage based on recognized architectural heritage and social memory. The paper presents a comparative study of the redevelopment of two former military barracks in Nis - Bubanjski Heroji and Filip Kljajic. These sites share the same disposition within the city but diverge in terms of their size, historical importance, and discourse of redevelopment. The comparison is presented from four perspectives: planning, built heritage, public perception, and cultural meaning. By examining the transformation of the complexes, the paper aims to perform a critical review which compares the reality of urban transformations in Serbia with the theoretical background and current urban regeneration policies promoted worldwide. This paper exploits the HUL approach, an integrated approach to urban management promoted by UNESCO, by extracting and analyzing four principles: the historical layering of cultural and natural heritage and attributes, dynamic character of urban space, promotion of social diversity, and balanced relation between artificial and natural. The conclusions highlight the difference between the local practices of commercially- and heritage-led redevelopment in order to suggest some improvements for similar redevelopment projects in the future.