This study focuses on the use of systematic social observations (SSO) to measure crime prevention through environmental design (CPTED) and disorder. To improve knowledge about measurement issues in small area research, SSO is conducted by means of three different methods: in-situ, photographs, and Google Street View (GSV) imagery. By evaluating the methodological quality of the observation methods, the results of our study suggest that virtual SSO approaches have considerable promise for the reliable assessment of physical properties of small areas. We discuss challenges and provide avenues for future research to encourage the evolution of a more reliable approach to measure the physical environment.