The wood pastures or hardwood rangelands of the southwestern Iberian Peninsula are complex social-ecological systems created from the long-term interaction of society and the landscape. Dehesa, oak woodlands managed for grazing, cropping, and other forms of production, is the most common rangeland system and one of the most distinctive landscapes. Traditionally characterized by multifunctional low-intensity management that enhances a wide range of ecosystem services, current management has shifted from the traditional toward more intensified models. This paper assesses the coproduction of ecosystem services on dehesa properties by exploring the relationship between biophysical and sociocultural factors and dehesa management practices. Based on 42 surveys we analyze 16 quantitative indicators using multivariate techniques. The results indicate that there are four main dehesa types as defined by their characteristics and management: large heterogeneous operations with diverse products; small and homogeneous operations focused on a reduced number of products; medium-large properties focused on crop production; and midsized properties with easy public access. Management is the result of the dynamics of interacting biophysical and sociocultural factors that influence manager priorities and investments. Management decisions group around the degree of multifunctionality of the operation, the relative importance of crop production, the degree of grazing pressure in the system, and how restrictive public access policy is. We find that in the study area, interactions between all the previously mentioned elements covary consistently, generating bundles of ecosystem services associated with each of three management models based on the intensity of management.