Governments across Central and Eastern Europe have enacted agri-environmental legislation over the past decade. This paper explores how the legislation has played out in practice, using property as an analytical lens to examine the social dynamics surrounding agri-environmental problems. The analysis proceeds by way of three case studies on irrigation management in Bulgaria, biodiversity conservation in the Czech Republic, and the preservation of open space in Poland. The findings highlight the discrepancy between the legal rights accorded to land owners and their rights-in-practice. Land owners contest the constraints imposed by agri-environmental legislation through strategies ranging from avoidance to open violation. They also counter the goal of environmental protection by invoking competing social values. The material and symbolic contestations form new sets of regulations blurring the boundary between public oversight and private rights delineated in agri-environmental legislation.