There is a disagreement in place-based research regarding whether objective indicators or individual perceptions of environments are better predictors of well-being. This study assessed environmental influences on well-being for 373 individuals with psychiatric disabilities living independently in 66 neighborhoods in the southeastern United States. Three questions were examined utilizing random effects models: (1) How much variance in personal and neighborhood well-being can be explained by neighborhood membership? (2) What is the relationship between participant perceptions of neighborhood quality and researcher ratings of neighborhood quality? and (3) What is the relative influence of individual perceptions, perceptions aggregated by neighborhood, and researcher ratings of neighborhood quality in predicting personal and neighborhood well-being? Results indicate that individual perceptions of neighborhood quality were more closely related to well-being than either aggregated perceptions or researcher ratings. Thus, participants’ perceptions of their neighborhoods were more important indicators of their well-being than objective ratings made by researchers. Findings have implications for measurement approaches and intervention design in placed-based research.