The transition towards nature-based cities has increasingly become a central focus in political–environmental agendas and urban design practices, aiming to enhance climate adaptation, urban biodiversity, spatial equilibrium, and social well-being as part of the ongoing socio-ecological urban transition process. Climate adaptation in cities is a complex problem and one of the main collective challenges for society, but the relationships between city managers and citizens as to urban green care still face many challenges. Parks design guided by technical-expert and globalised criteria; inflexibility from bureaucratic inertia; and citizens’ demands to participate in the urban green transition, sometimes without the necessary knowledge or time, are some of the challenges that require further research. In this study, we examine four long-lasting approaches to green-space management in four cities in the Netherlands, ranging from municipality-driven to community-driven management forms, and encompassing diverse spatial configurations of greenery within the urban fabric. Utilising the theoretical lens of the Social–Ecological Systems Framework, we employ a multiple-case-study approach and ethnographic fieldwork analysis to gain a comprehensive understanding of the norms, collective-choice rules, and social conventions embodied in each urban green management arrangement. The purpose of this research is applied, that is, to provide urban managers and decision-makers with a deeper understanding of drivers to promote effective collaborative management approaches, focusing on specific organisational rules that may contribute to more sustained planning and maintenance pathways for urban green spaces, regardless of changes in political leadership or significant external funding sources. The results of the investigated cases show that long-lasting collaborative management of forests and parks has established a set of collective-choice rules for resource transfer between municipalities and citizens, including non-monetary resources (such as pruning-training courses or guided tours that attract tourists and researchers). Additionally, these arrangements have been favoured by the existence of legal norms that enable co-ownership of the land, and monitoring and sanctioning mechanisms that offer a slightly different interpretation from the evidence identified so far in the scientific literature on collective resource management and organisational studies.