In this paper, we propose the integration of mobile-based and web-based Interfaces called City Probe system for the spatial identification and assessment driven by citizens’ participation. The City Probe system provides the potential method to engage the power of citizens’ participation in the city governance. It allows citizens’ on-site and off-site identification and assessment of contextual features. The City Probe system sets up the measuring rule from −10 (most negative) to +10 (most positive) to standardize citizens’ participation. Individual citizens can quantify their contextual feature identification into assessable standard. Three kinds of maps including DOT, BLOCK, and HEAT modes can be made and visualize the quantitative results. The experiment based on the City Probe Mobile APP is conducted according to the features pre-made by subjects. It demonstrates how the City Probe system could be adopted to almost any contextual feature. The results also use visualized maps to present the potential positive (blue) and negative (negative) areas of target features derived from subjects’ participation.