Throughout the 1960s, the urban peripheries in several Portuguese colonial cities embarked on a profound process of transformation. With different urban histories and distant geographical contexts, Lisbon and Luanda were united by urban planning and public policies defined by the Estado Novo’s response to the lack of housing supply. The neighbourhoods that expressed modern affiliation in their architecture witnessed profound changes brought about by the April 25th Revolution and the consequent process of democracy in Portugal (1974) and independence in Angola (1975). This article proposes a comparative analysis of middle-class housing complexes, demystifying the urban peripheries by an optimistic architecture that helped shape the built environment and echoed its time’s urban and political concerns. It analyses four case studies, taking into account their inherent characteristics (urban layout, architecture, and interior design), their significance as a testimony to the social and political aspirations of the time, and the quality of life and lifestyles of their current population. It draws on sociological surveys and analysis of plans, photographs, and maps to carry out a broader picture of modern housing through the work of Fernando Silva in Lisbon and Fernão Simões de Carvalho in Luanda. Based on current research, this article aims to assess the resilience of these neighbourhoods by analysing the housing landscape from an urban and architectural perspective. By mapping the changes after 50 years of use, the intention is to understand how they have adapted to current conditions (urban and social) and support future actions.