Globally, current food consumption and trade are placing unprecedented demand on agricultural systems and increasing pressure on natural resources, requiring tradeoffs between food security and environmental impacts especially given the tension between market-driven agriculture and agro-ecological goals. In order to illustrate the wicked social, economic and environmental challenges and processes to find transformative solutions, we focus on the largest concentration of greenhouses in the world located in the semi-arid coastal plain of South-east Spain. Almería family farming, predominantly cooperative, greenhouse intensive production, commenced after the 1960s and has resulted in very significant social and economic benefits for the region, while also having important negative environmental and biodiversity impacts, as well as creating new social challenges. The system currently finds itself in a crisis of diminishing economic benefits and increasing environmental and social dilemmas. Here, we present the outcomes of multi-actor, transdisciplinary research to review and provide collective insights for solutions-oriented research on the sustainability of Almeria’s agricultural sector. The multi-actor, transdisciplinary process implemented collectively, and supported by scientific literature, identified six fundamental challenges to transitioning to an agricultural model that aims to ameliorate risks and avoid a systemic collapse, whilst balancing a concern for profitability with sustainability: (1) Governance based on a culture of shared responsibility for sustainability, (2) Sustainable and efficient use of water, (3) Biodiversity conservation, (4) Implementing a circular economy plan, (5) Technology and knowledge transfer, and (6) Image and identity. We conclude that the multi-actor transdisciplinary approach successfully facilitated the creation of a culture of shared responsibility among public, private, academic, and civil society actors. Notwithstanding plural values, challenges and solutions identified by consensus point to a nascent acknowledgement of the strategic necessity to locate agricultural economic activity within social and environmental spheres.This paper demonstrates the need to establish transdisciplinary multi-actor work-schemes to continue collaboration and research for the transition to an agro-ecological model as a means to remain competitive and to create value.