Acquiring sociospatial experiences at nested geographical scales is a lifelong meaning construction process, and this has great implications for aging in place. Various experiences trigger older people’s attitudinal and sentimental reflections regarding how they evaluate and attach themselves to where they live; this invokes residential satisfaction, and subsequently, place attachment. Through a questionnaire survey of 501 community-dwelling individuals aged sixty-five and older in Hong Kong, an ultra-high-density Asian city, this article examines the relationship between sociospatial experiences and well-being through a sequential path analysis model. It identifies five dimensions of sociospatial experiences: “homes and housing estate,” “social environment,” “living convenience,” “pedestrian experience,” and “blue and green” features. All dimensions predict emotional, social, and psychological well-being via residential satisfaction and then place attachment. Place attachment is a more robust mechanism than residential satisfaction in the environment–well-being association. Developing a satisfying relationship, and subsequently, functional and emotional links with the place of residence, is conducive to achieving well-being. This uncovers an important mechanism of person–environment interactions for aging in place.