Community development tends to focus on large-scale, government-funded transformations or on small-scale, grassroot initiatives. In the US, the financial resources, available infrastructure, and broad-based civic support to implement large-scale community transformations are frequently lacking. In contrast, niche interventions, while often locally successful, tend to be unscalable. Accordingly, many community development programs either do not go beyond an ideational stage, or they are unscalable or unsustainable in the long run. In this qualitative case study, we analyze the Eastern Market in Detroit, Michigan, a local institution that contributes considerably and in several ways to the sustainability of multiple communities. Using Content Configuration Analysis (CCA), we conduct a bottom-up exploratory analysis of fieldwork notes, nonparticipant observations, as well as audio, visual, and written materials including policy and strategy documents from the City of Detroit, Wayne County, and the State of Michigan, academic publications, strategy and annual reports, websites, blogs, vlogs, social media outlets, newspapers, podcasts, and interviews along two lines of inquiry: first, to examine how the market contributes to sustainable community development and, second, to explore the systemic underpinnings that facilitate such development. Specifically, we focus on the Eastern Market to identify system-relevant actors, interests, relations, interventions, and outcomes that illustrate an institution which operates well beyond the ideational confines of a conventional farmers market. In the process of exploring the adaptive nature of the Eastern Market within its financial and infrastructural constraints, we also exemplify with this case that a well-established institution, a farmers market, can reinvent itself to serve multiple needs of larger, heterogeneous communities, and that the successful adaptations associated with this reinvention reimagine the community in which it is embedded.