As climate change continues to manifest its effects globally, the built environment faces escalating challenges in maintaining functionality and resilience against extreme weather events. This study analyses the interaction between functional service life and building resilience amidst climate change impacts, focusing on contrasting regions within Chile: the north and extreme south. Through a series of 158 case studies, this research examines how buildings in these regions adapt and endure under changing climatic conditions. Employing a qualitative and quantitative approach, data collection involved on-site inspections, interviews with stakeholders, and analysis of historical records. The findings underscore the importance of localized solutions tailored to the specific climatic challenges faced by each region. Furthermore, the research highlights the significance of proactive measures such as robust design, materials selection, and maintenance protocols in enhancing building resilience. By synthesizing insights from diverse climatic contexts, this study contributes to a broader understanding of the complex dynamics shaping the functional service life and resilience of buildings in Chile. Finally, the findings offer some guidance for different stakeholders seeking to enhance the built environment against the escalating impacts of climate change.