Medieval European urbanization presents a line of continuity between earlier cities and modern European urban systems. Yet, many of the spatial, political and economic features of medieval European cities were particular to the Middle Ages, and subsequently changed over the Early Modern Period and Industrial Revolution. There is a long tradition of demographic studies estimating the population sizes of medieval European cities, and comparative analyses of these data have shed much light on the long-term evolution of urban systems. However, the next step—to systematically relate the population size of these cities to their spatial and socioeconomic characteristics—has seldom been taken. This raises a series of interesting questions, as both modern and ancient cities have been observed to obey area-population relationships predicted by settlement scaling theory. To address these questions, we analyze a new dataset for the settled area and population of 173 European cities from the early fourteenth century to determine the relationship between population and settled area. To interpret this data, we develop two related models that lead to differing predictions regarding the quantitative form of the population-area relationship, depending on the level of social mixing present in these cities. Our empirical estimates of model parameters show a strong densification of cities with city population size, consistent with patterns in contemporary cities. Although social life in medieval Europe was orchestrated by hierarchical institutions (e.g., guilds, church, municipal organizations), our results show no statistically significant influence of these institutions on agglomeration effects. The similarities between the empirical patterns of settlement relating area to population observed here support the hypothesis that cities throughout history share common principles of organization that self-consistently relate their socioeconomic networks to structured urban spaces.