With latest development of telecommunication technologies and end user's increased bandwidth and mobility demand reachability of information and communication technologies (ICT) became more critical. In this paper, we approach to end user behaviors and the reachability to ICT by tackling digital divide concept along with clustering analysis. To the best of our knowledge, this research is a unique case study that attempts to analyze digital divide at intra-city level by neighborhoods. While governments and institutions, such as ITU, are in question of whether the global divide is widening or narrowing, there are no studies, neither in the literature nor in practice to understand the gap between ICT users in a city. With this goal, Istanbul habitants were asked to fill a questionnaire, in order to be classified in terms of their technology reachability and reasons of using ICT. Then, clustering analysis was performed to questionnaire results. Respondents have been clustered into sub groups from digital divide perspective. The required steps and suitable clustering techniques during this process are discussed with determination of questions at the end which are commonly answered by respondents with different ICT knowledge, which may lead us determine precise reasons of digital gap later on.