Amid trends of privatization, financialization, and decreasing access to agricultural land, there is a call for more sustainable and equitable land tenure and access. In response, I present four cases as interventions into the story of private property in the Canadian prairies, asking how stakeholders negotiate the multiple and sometimes competing functions of agricultural land in economic development, food production, conserving and enhancing ecological resources, recreation, and reconciliation. In qualitative studies of a) persuasive stories used by respondents to government consultations on land ownership to foster change b) public responses to changes in trespassing legislation, c) conflict and collaboration among stakeholders managing land for agri-environmental goals in alternative grazing land tenure models and d) a network of settler landholders sharing land with Indigenous land users, I employ critical realism to analyse interviews and secondary data. I consider questions of rights and responsibilities to land, mechanisms of inclusion and exclusion from land, the public good, and the discourse and actions that challenge or legitimize land access/tenure practices and related policies/legislation. Each case also explores the possibility of different futures for land regimes based on changing social relations as people work to challenge or further entrench private property rights. Alternatives to private land ownership cultivate diverse relationships in relation to, and with, land and people.