Floods pose a significant threat to road networks globally, disrupting transportation, isolating communities, and causing economic losses. This study proposes a four-stage methodology (avoidance, endurance, recovery, and adaptability) to enhance the resilience of road networks. We combine analysis of constructed assets and asset system performance with multiple disaster scenarios (Reactive Flood Response, Proactive Resilience Planning, and Early Warning Systems). Advanced flood Geospatial-AI models and open data sources pinpoint high-risk zones affecting crucial routes. The study investigates how resilient assets and infrastructure scenarios improve outcomes within Urban Resilience Index (CRI) planning, integrating performance metrics with cost–benefit analysis to identify effective and economically viable solutions. A case study on the Lisbon Road network subjected to flood risk analyzes the effectiveness and efficiency of these scenarios, through loss and gain cost analysis. Scenario 2, Proactive Resilience Planning, demonstrates a 7.6% increase compared to Scenario 1, Reactive Flood Response, and a 3.5% increase compared to Scenario 3, Early Warning Systems Implementation. By considering asset performance, risk optimization, and cost, the study supports resilient infrastructure strategies that minimize economic impacts, while enabling communities to withstand and recover from flood events. Integrating performance and cost–benefit analysis ensures the sustainability and feasibility of risk reduction measures.