The paper proposes an analysis of the social–ecological resilience of the Limarí Basin, an agriculture-intensive dryland in the north of Chile, featuring one of the most innovative market-based water managements and the most active water rights market in the country, but concurrently affected by an ongoing water stress situation. The Chilean water market, one of the main examples of the application of neoliberal policies in water management, has received mixed appraisals although, at present, few empirical studies evaluate the social and environmental conditions associated with their operation. This paper, on the contrary, maintains the necessity to assess the capacity of market-based models to face situations of water stress, particularly since mega-drought phenomena are projected to become a recurring and increasing problem during the following decades because of climate change. The study offers a mixed bottom-up and top-down qualitative empirical analysis of how the Chilean water market operates, providing relevant insights into four dimensions of the social–ecological resilience of the watershed: redundancy, diversity and flexibility; connectivity, collaboration and collective action; social–ecological memory and learning; self-organization and governance of system changes. The conclusion is that water scarcity is self-produced: despite the flexibility provided by market-based water management, the combined effect of strong deregulation, of the absence of territorial planning and integrated management of water resources, and of short-term attitudes and generalized mistrust, has led the system to the critical situation it is now facing.