Fresh pasteurized milk consumption is evaluated from environmental and socio-economic perspectives. Two different supply chains are analysed: traditional supply chain and vending machines—a circular business model based on a short supply chain. Milk vending machines show that consuming milk in proximity, eliminating intermediaries between producers and consumers and, therefore, reducing the use of resources and energy (packaging and transportation), has environmental advantages. Hence, milk distribution, electricity consumption and consumer transport caused the largest impacts. When the environmental profiles of pasteurized milk consumption in supermarkets and vending machines are benchmarked, the vending machine has a considerable lower impact. The sensitivity analysis emphasizes the latter findings, highlighting the relevance of consumer choices upon the environmental profile of milk consumption. Despite the environmental benefits, vending supply chain unexpectedly failed in Spain from a socioeconomic point of view due to several factors: the farmers’ lack of processing and marketing capacities, the difficulty of networking and collaboration with other key stakeholders, the necessity to raise consumer awareness of the benefits of pasteurized milk and the limited range of dairy products offered. The development of a close short supply chain can bring significant environmental and socio-economic benefits. Notwithstanding, the case analysed in this paper indicates that the isolated entrepreneurship is not sufficient and the transformation of the food system towards a circular model requires political and societal commitment.