The significant energy demands of wine production pose both a challenge and an opportunity for adopting a low-carbon, more sustainable and potentially less expensive energy model. Nevertheless, the (dis)incentives for the wider adoption of local production and self-consumption of energy (also known as “prosumerism”) from renewable energy sources (RESs) are still not sufficiently addressed, nor are the broader social–ecological benefits of introducing RES as part of a sustainable viticulture strategy. Drawing on the social–ecological systems (SESs) resilience framework, this article presents the results of a Living Lab (an action-research approach) implemented in Alentejo (South of Portugal), which is an important wine-producing Mediterranean region. The triangulation of results from the application of a multi-method approach, including quantitative and qualitative methods, provided an understanding of the constraining and enabling factors for individual and collective RES prosumer initiatives. Top enablers are related to society’s expectation for a greener wine production, but also the responsibility to contribute to reducing carbon emissions and energy costs; meanwhile, the top constraints are financial, legal and technological. The conclusions offer some policy implications and avenues for future research.