<p>The energy transition in districts is urgent and complex, necessitating new forms of stakeholder collaboration to address these challenges. In certain districts, decentralized technologies such as heat pumps present promising solutions for heating transitions. However, the transition in the building sector is slower than needed, and despite existing support mechanisms, many property owners hesitate to adopt measures that would facilitate the heating transition. To address this lack of engagement, the city of Freiburg implemented the Klimaquartier Waldsee project, an urban pilot aimed at fostering citizen engagement for sustainability. Within this project, various co-learning and co-creation formats were developed, iteratively designed, and formatively monitored. Using a conceptual framework outlining the “property owners’ journey toward climate-friendly heating,” recommendations for practitioners were developed to overcome property owners’ barriers. The steps toward adopting climate-friendly heating technology in properties are manifold, presenting diverse barriers along the way. Different countermeasures addressing exchange, information, mentoring, and strategic tasks can help mitigate these barriers. These countermeasures can be organized through social innovations, such as an “Infopoint” that combines proven and new concepts synergistically and supports practitioners in optimizing their assistance to property owners. The social innovation concept was co-evaluated by key actors of the Klimaquartier itself. Urban experimentation can lead to improved governance by bringing together key actors on topics such as positive energy districts. However, careful design and systematic monitoring are crucial for learning from experimental interventions and enabling the development and upscaling of promising new governance tools.</p>