This article investigates the relevance of the work of the Latin-American thinkers Humberto Maturana and Paulo Freire to learning-based transformations towards sustainability. This analysis was inspired by a case study of a Brazilian urban community seeking to develop pathways towards sustainable living and was informed by a review of their key works. The paper aims to obtain a better conceptualization of learning-based transformations and provide insights into collective learning processes focused on advancing sustainable practices. We present notions of the transformative social learning approach that underpins the case study, using the concepts of Maturana and Freire as a lens. Our results indicate the importance of a relational approach in fostering collective learning processes. Finally, we derive three principles that can guide such processes: (1) facilitating transformative interactions between people and places, (2) enabling dialogic interaction within a climate of mutual acceptance, and (3) creating space for ontological pluralism.