Increasing volumes of spatial data about urban areas are captured and made available via volunteered geographic information (VGI) sources, such as OpenStreetMap (OSM). Hence, new opportunities arise for regional exploration that can lead to improvements in the lives of citizens through spatial decision support. We believe that the VGI data of the urban environment could be used to present a constructive overview of the regional infrastructure with the advent of web technologies. Current location-based services provide general map-based information for the end users with conventional local search functionality, and hence, the presentation of the rich urban information is limited. In this work, we analyze the OSM data to classify the geo entities into consequential categories with facilities, landscape and land use distribution. We employ a visual overlay of heat map and interactive visualizations to present the regional characterization on OSM data classification. In the proposed interface, users are allowed to express a variety of spatial queries to exemplify their geographic interests. They can compare the characterization of urban areas with respect to multiple spatial dimensions of interest and can search for the most suitable region. The search experience is further enhanced via efficient optimization and interaction methods to support the decision making of end users. We report the end user acceptability and efficiency of the proposed system via usability studies and performance analysis comparison.