While governments worldwide develop policies to promote urban densification, critics point to possible negative effects of densification on social sustainability. The occurrence and distribution of these negative social effects are strongly influenced by land policies. This makes it crucial to monitor the role of land policies and understand what processes shape urban development in the context of densification. To do so, detailed, large-scale international comparisons of densification patterns, including building and social changes, are needed. We address this issue by introducing a method to measure and compare urban development in two countries with contrasting planning systems: the Netherlands, where public actors play a strong and active role, and Switzerland, where strong private property titles and a highly democratic planning system are prevailing. Our GIS-based method analyses densification processes within their surrounding morphological and socio-demographic context. A k-proto cluster analysis on highly detailed spatial and statistical data based on housing units, covering 2011–2019, results in five densification types. The distribution of these types reveals different patterns in the two city regions of Utrecht (NL) and Bern (CH). Most strikingly, contiguous redevelopments frequently occurred in Utrecht but hardly in Bern, pointing at possible advantages for Dutch municipalities to intervene in property rights. While having developed an empirical basis in this study, future research that refines the analysis of the legal, planning and ownership conditions underlying the identified densification patterns can contribute significantly to policy evaluation.