Given its integrated benefits, urban agriculture, especially community gardens, may significantly enhance the socio-environmental condition of vulnerable districts and communities. This review examined different aspects of urban agriculture to highlight its value beyond profitability and food production in terms of social empowerment, health, and well-being. The paper seeks to understand the reasons behind the failure of a community garden initiative that took place in a distressed urban area of the city of Rome and to clarify the connections between community garden initiatives, socioeconomic context, and urban structure. Multiple-case study research was conducted to compare successful best practices with the case study mentioned above to identify invariants and draw cross-case conclusions. All case studies are linked to bottom-up processes in marginal areas where public space could represent a catalyst capable of embracing cultural, social, environmental, and eco-systemic matters. The study indicates how critical elements for a successful and long-lasting implementation of community garden initiatives must include identification of the community's primary needs, institutional and financial support, extensive engagement of inhabitants, and the role and diversification of stakeholders. These aspects drive the meta-design phase and long-term planning of the overall process.