Designed by Álvaro Siza at the turn of the twentieth century, the Terraços de Bragança housing complex exemplifies his ability to harmonize contemporary architecture with Lisbon’s historic urban fabric while navigating a complex architectural production chain. Siza’s prior experience with the Chiado reconstruction, following the 1988 fire, deepened his understanding of Pombaline architecture and provided him valuable connections with planning authorities and stakeholders. The project showcases Siza’s strategies for urban integration, including the adaptive reuse of architectural forms, the creation of new volumes within traditional layouts, and the use of materials that blend seamlessly with the historical setting while maintaining a timeless identity. Its typological and morphological elements reflect parallels with Lisbon’s historic scale, volume, and spatial configuration. This research explores the interplay of architects, engineers, developers, and clients, revealing how diverse perspectives influenced the project’s outcomes, from regulatory compliance to market demands. Siza’s “starchitect” status also played a pivotal role, marking one of the first instances in Portugal where an architect’s authorship was a key marketing tool. The study highlights Terraços de Bragança as a model of sensitive architectural practice, offering insights into the challenges and opportunities of designing contemporary spaces that respect and enhance historically significant settings.