Cultural heritage drives and enables sustainable urban development. The adaptive reuse of cultural heritage creates values while prolonging the lifespan of heritage. Similarly, circular economy creates value while extending the useful life of materials and elements through their reuse. Existing studies on adaptive reuse challenges seldom focus on cultural heritage properties, and they are often identified through the engagement of a limited variety of stakeholders, as compared to the actors normally involved in adaptive reuse. Filling this gap, this paper provides a preliminary baseline of challenges faced by the city of Amsterdam from the perspective of various involved stakeholders, and suggests solutions to address them. The participants represented the public, private, knowledge, and third sectors. The methods used were the following: for data collection, a multidisciplinary workshop using the steps of the Historic Urban Landscape approach as an assessment framework applied to multiple scales on adaptive reuse, and for data analysis, manifest content analysis. The results expanded the range of challenges and solutions reported by previous literature on the adaptive reuse of cultural heritage in content and scale by identifying 61 themes—e.g., knowledge and civic engagement. Tools and stakeholders were also identified. These findings provide a reference for future practice, policymaking, and decision-making, facilitating the adaptive reuse of cultural heritage to capitalize on its potential for sustainable development and circular economy.