ABSTRACT The redevelopment and management of brownfield sites by grassroots cultural organizations have been shown to have a transformative role on communities and cities, implementing bottom-up culture-led urban regeneration rather than top-down models which often lead to gentrification. Based on analyses and interviews with actors from major grassroots cultural centres in Berlin (ufaFabrik) and Bratislava (Nová Cvernovka), this study challenges previous research on cultural brownfields focusing on temporary artistic interventions, arguing instead that long-term commitment, care, participation and cooperation between cultural organizations and local administrations can lead to more sustainable regeneration models in which cultural brownfields operate as commons-based ecosystems of care. The study also offers a unique insight into the “western” vs. “eastern” specifics, highlighting the fact that post-socialist administrations can serve as a barrier to a successful redevelopment through stigmatized public-NGO relationships, where artists and communities are often perceived as a “political opposition”.