The available sustainability tools and rating systems need to better incorporate the broader socioeconomic settings associated with the built environment. This paper develops, and contributes to the current body of knowledge, two innovative system-based benchmarks for sustainability assessment. On one hand, the "work" benchmark defines the behavioral relationships between the construction products and actors to study technical, social and cultural, and economic sustainability. On the other hand, the "nature" benchmark defines the interactions between construction processes and the surrounding ecosystems to study environmental, individual, and economic sustainability. The authors developed and distributed an expert survey to validate these two benchmarks. Consequently, to test these two novel concepts, the authors analyzed three different civil infrastructure projects. To this end, the authors evaluated the actors, products, and dynamics within the construction processes and their interactions. The analysis provided insights related to degrees of communication between communities and the construction industry, and highlighted occurrences of a lack of communication. The relationship between the construction industry and its customers was also investigated, and it was clear that within a single construction project, all sustainability indicators can cross boundaries and overlap. Based on the results, the authors succeeded in: (1) defining a holistic sustainability systems-based approach to studying the built environment; (2) assessing the degree of communication between the construction industry and its community host systems; and (3) evaluating the relationship between the construction industry and its customers. For future work, the authors are developing a flow benchmark to predict the overall system change through overtime simulation of human-built environment resource dynamics.