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This article examines the role of legal actors in mediating urban land conflicts involving informal settlements and the social and environmental functions of private property. This problem reveals the challenges of conciliating two constitutional rights—the right to adequate housing and the right to a healthy environment. Methods include an analysis of the urban policy and legal framework regulating environmental protection, housing provision, property rights, and land use law. The legal case analysis of Ocupação Anchieta, a young land occupation in São Paulo’s periphery, offers additional evidence through interviews with key informants, fieldwork including household surveys, participatory planning meetings, direct observation, and mapping of existing conditions. Findings demonstrate that private property rights continue to have uncontested power in the legal system, especially during the first years of an informal settlement. Furthermore, planning regulations do little to help young land occupations, vis-à-vis consolidated informal settlements, in establishing sustainable practices from the beginning. Peripheral urbanisation through informal land occupations of environmentally protected areas remains one of the most pressing problems of the Global South. Thus, legal actors and planners should develop land use laws, urban policy, and mechanisms of private property conflict mediation that distinguish between young land occupations and consolidated informal settlements.