The post-socialist urban restructuring of Skopje, North Macedonia has been characterized by significant changes in the built fabric of the city, resulting from the political, economic and societal processes following the dissolution of Yugoslavia. In early 1990s and post-privatization, there was a dynamic transformation of the city’s housing stock in post-WWII prefabricated apartment buildings. Flat owners in socialist-era housing estates in Skopje modified their apartments by expanding and enclosing balconies, thus gaining more living space. Garages were converted into shops and ground-floor and first-floor apartments were renovated into offices, resulting in commercialization of previous residential space. To better understand the spatial disorder triggered by transformation of housing estates during the lengthy transition from a centrally-planned system to a market economy, this article evaluates various spontaneous and planned practices of transformation of residential space in housing estates in post-socialist Skopje. We analyze these changing practices of transformation through fieldwork and focus group discussions with residents. We also review archival material and administrative and legal documents, including municipal master plans and national planning laws and decisions related to housing estates in post-1991 Skopje. Findings emphasize the complex interplay between many actors, ideologies and interests that shape the experience of urban life in post-socialist Skopje, evidenced by outcomes related to housing choice and renovation practice, especially the enclosure of balconies for providing more living space. Such interventions are viewed as important steps towards improving living conditions in prefabricated apartment buildings in Skopje. Individual decisions about apartment renovation affect urban planning at the neighborhood level, and the findings from this research thus inform residential mobility and neighborhood-level strategic decision making. The aim is to help neighborhoods—built in an earlier socio-political era under a central planning system—to adapt to future demands.