There is a lack of emphasis in the planning world, both academically and in the field, on preventing crime. Defensible Space and Crime Prevention through Environmental Design (CPTED) has been the two main approaches taken by planners and criminal justice officials that is design-based and that has brought some level of collaboration between the two professions. This study will analyze the built environment of select crime hotspots in the city of Boston from a design-based crime prevention perspective in order to draw correlations between high crime areas and elements of design-based theories. Using GIS, a kernel density analysis is conducted in 8 of the 13 neighborhoods in the city of Boston. Pictures taken during field observations of the hotspots are used to compare strong and weak examples of design-based crime prevention theories. A CPTED matrix is also used to provide a weighted score to Roxbury, a neighborhood that ranks high in both property and violent crime. Overall, the kernel density results reveal that the hotspots in Roxbury tend to be higher in quantity but less dense and smaller in size than other Boston neighborhoods. This study reveals that for poorer neighborhoods the condition of land uses seems to be a more prevalent factor of the physical environment than the land-use mix that are exhibited in middle and upper class sections of the city. Urban planners play a key role in bringing together and maintaining land uses that will be less conducive to crime given a neighborhood’s or greater geographic area’s history and current socioeconomic and crime context.