Using the “user-centered” design perspective and the construct of design “humanization” as theoretical underpinnings, this field study verified the role of “objective” design quality of residential facilities for the elderly in the prediction of “subjective” users’ psychological responses. A sample of over-65-year-old adults (N = 114) was recruited in eleven residential facilities, which differed for the degree of “objective” design humanization (rated on the basis of a design expert assessment). Participants had to fill in a questionnaire including measures of both specific perceived environmental qualities (spatial-physical and social-relational) and more general psychological responses (such as residential satisfaction and psychological well-being). Outcomes revealed that older residents living in high-humanization structures show higher scores of residential satisfaction, psychological well-being and perceived environmental qualities than those living in low-humanization structures. Moreover, significant correlations emerged between specific perceived environmental qualities of the facility and general psychological outcomes. These results confirm the importance of design features for supporting elders’ needs and fostering their quality of life.