This study examines the relationships between commonly available socio-economic and environmental determinants of real estate (crime, quality of schools, racial/ethnic diversity, and built environment) and real estate values in socially and politically recognized units in the three largest cities of the U.S.—New York, Los Angeles, and Chicago. Utilizing a variety of data sources used by potential real estate buyers, we conduct correlations, mapping, and multiple regression analyses to identify the degrees and strengths of associations between select determinants and real estate values at these politically recognized units. Results suggest that the cities exhibit similar patterns for crime-related characteristics and quality of schools. However, the characteristics such as population density, vacancy rates, and especially the ethnic/racial diversity of these recognized units demonstrate nuanced differences with real estate values across the three cities