“Age-Friendly Cities and Communities” is an initiative launched by the WHO in 2007 that has spread to more than 1000 cities and communities around the world. This initiative is based on an integrated physical and social environment for older people, and a model of participatory, collaborative governance. An enabling social environment setting is just as important as material conditions in determining well-being in later life. The objective of this study is to analyze the interaction between age-friendliness (physical and social) and subjective well-being in women and men aged 55 and over in the Basque Country. The methodology was based on a survey of a representative sample (n = 2469 individuals). In order to know the predictive power of age-friendliness over subjective well-being, linear regression models separated by gender were constructed. The predictive models of age-friendliness are composed by different variables for men and women. In both cases, the physical environment variables do not remain in the final model. Among the predictors of well-being in men, the coexistence stands out as a safety and support network. In women, the neighborhood has proved to be a very important resource. The conclusions of this study contribute to literature and interventions promoting more effective strategies that enhance older people well-being, considering the gender perspective.