AbstractGreen-Win is the proposal where that government, society, and business can all reap benefits while at the same time playing a vital role in the transition to sustainable development and lower carbon futures. We argue that, while the Green-Win proposition is central to many state and expert models of sustainability transitions, as a construction, it belies more complex trade-offs and cognitive models of sustainability and societal transitions. Cultural models are cognitive representations shared by a community which provide bothmodels ofthe world, which aid in interpreting what is in the world, how it works, what is possible (or not) and why, andmodels forthe world, which suggest how to act in it to bring about desired outcomes (cf. Geertz 1973). We surveyed 225 respondents in Shanghai, China, Istanbul, Turkey, and Beirut, Lebanon to assess their basic beliefs about sustainability, specifically whether it is possible to implement concrete practices that realize environmental sustainability goals in conjunction with economic development—the Green-Win proposition. We found important similarities and differences among urban stakeholders’ cultural models of sustainable development. For example, Chinese and Lebanese respondents displayed a strong belief that economic growth and environmental sustainability are compatible, while Turkish respondents showed significant disagreement with this proposition. We argue that such basic notions about the possibility of Green-Win opportunities between environmental sustainability and economic development are important to understand in the context of mitigating and adapting to climate change in critical urban environments. Cultural modelsofandforgreen development may either enable or inhibit transformations in urban systems according to local conditions. Finally, we discuss the potential implications of cultural models’ research for targeting communications and engendering collaborations among diverse stakeholders in order to align perspectives and overcome barriers that may otherwise limit successful visioning, planning, and implementation for transformation towards sustainable development.