In a study comparing the satisfaction of older adults (1200 men and women aged 55 years and older) with their neighborhoods in different urban and rural regions in East and West Germany we found considerable differences. Our paper will present the results of hierarchical regression analyses including objective and subjective predictor variables, showing the importance of subjective evaluations of different neighborhood conditions. The findings can contribute to a better understanding of person-environment relations for the future planning of urban environments suitable for the well-being of the people.