Housing cooperativism in Chile shows a discontinuous trajectory through different arrangements between the State, the market, and civil society. Since the mid twentieth century, cooperatives and self-organised housing developed alongside each other. While cooperatives for waged workers were supported by the government, a self-managed housing movement grew amongst the popular classes. The Military Dictatorship and its neoliberal reforms from 1973–1989 meant the demobilization of both groups and the fracture of the existing knowledge of self-organisation and cooperativism in housing. Despite this rupture, since the 2000s, cooperatives are re-emerging thanks to renewed links with Latin-American cooperativism and government’s support to self-management. From a historical perspective, we examine the main challenges faced by the re-emerging cooperatives amidst a persistent neoliberal policy environment. Our theoretical lens combines cooperative value-orientations with examples of agency in the new cooperatives. We conclude that the future of housing cooperativism in Chile depends on its positioning between ‘pragmatic’ and ‘reformist’ values to align with their environment.