The recent diffusion of urban sustainability concepts has pushed new developer-driven master-planned models of sustainable neighborhoods to emerge around the world. Once built, project assessments usually reported higher-than-expected resource consumption and various operational challenges, which kept these neighborhoods from fully meeting their sustainability goals. Many experts have attributed such challenges to wrong design decisions and lack of accountability post-operation, while social scientists criticized developers for greenwashing their projects. I draw from communication studies, actor-network theory, and urban studies to frame these new projects as an eco-system of dynamic cultural iterative processes rather than a linear design, construction, and delivery process. I recognize sustainable neighborhoods as spaces with multiple identities and actor interrelations. They are spaces produced through various overlapping stories. Hence, the assessments and indicators used to evaluate these neighborhoods must be based on different actors' expectations and use-values. This dissertation is comprised of three standalone articles that make independent scientific contributions to the same problem. In the first article I conducted textual analysis on popular press articles portraying new master-planned sustainable neighborhood projects in three countries. In the second and third articles, I carried in-depth go-along interviews with 46 residents, developers, designers, and various professionals involved in developing and managing a sustainable neighborhood. I developed an actor-indicator matrix map, connecting preferred evaluation indicators with different actor groups. In addition, I mapped the fundamental controversies that might affect the performance of market model of sustainable neighborhoods according to different actors. The results in the first article indicate that the press often represents such projects as utopians ignoring issues related to performance and management, which might create unrealistic expectations. Findings from the second article suggest that users and diverse local actors will prioritize different metrics than expert-based models when allowed to express their opinions. In the third article I mapped five main controversies fundamentally associated with the performance of privately developed sustainable neighborhoods: branding, innovation, behavior, governance, and market dynamics. I develop recommendations that can limit the rise of similar controversies in future developments. Recommendations include tax deductions for residents who choose to live in a sustainable neighborhood, a code of conduct to regulate behavior in sustainable neighborhoods, and resident representative committees to enhance the civic agency of the residents. Taken together, these 3 articles suggest a need for new analytical lenses to address the practical challenges that face market driven sustainable neighborhoods post operation. It is evident that operational success is not only limited to executing optimal designs and technologies; factors such as communication, expectations, choice of indicators, and competing priorities within the ecology of actors all interfere with the success of a market-driven sustainable neighborhood.