Swedish municipalities are taking an active role in shaping and implementing sustainability-related policies in urban development by initiating and governing sustainability-profiled district developments on municipally owned land. To drive sustainable development and innovation in these districts and develop future policies, municipalities use land allocation agreements to set project-specific sustainability requirements on housing development projects that go beyond the current national building regulations. Developers play a key role in implementing these municipal sustainability requirements. The purpose of this paper is to explore housing developers’ perceived barriers to implementing municipal sustainability requirements in their projects, which ultimately constrain possibilities for municipalities to drive sustainable development. Findings are based on case studies of two sustainability-profiled district developments in different Swedish municipalities. Main barriers perceived by the developers could be categorized into: (1) increased costs when adapting to unforeseen changes that constrain project budgets and (2) conflicting interests and objectives between interdependent actors. These barriers are contextualised within the relationship between the developers and municipalities. Contributions are made to literature on developers’ roles and perspectives in sustainability-oriented urban development. We illustrate how conflicting short-term and long-term interests between developers and municipalities complicate and impede problem solving in housing development projects. This calls for more research on these actors’ interests, and how they align and conflict in these types of projects. Findings also illustrate how developers resolve issues through interactions with municipalities, indicating collaborative problem solving processes to investigate further.