To ensure smart and sustainable urban environment, it is necessary to continuously assess the actions and needs of all three groups of stakeholders: government, business, and citizens. In order to develop a consistent approach towards such monitoring, it is important not only to consider the three areas of sustainability—economic, environmental, and social—but also to analyze the needs and attitudes of citizens towards smart sustainable development (SSD). This research establishes a framework for monitoring SSD and applies it to Boksitogorsk, a town in Leningrad oblast. The findings reveal existing gaps between stakeholder groups, likely stemming from ineffective communication. By implementing a robust SSD monitoring framework, this study enhances the existing literature on SSD and offers valuable insights for practitioners aiming to create more sustainable policies.