To date, the predominant tools for the evaluation of built environment quality and impact have been surveys, scorecards, or verbal comments—approaches that rely upon user-reported responses. The goal of this research project is to develop, test, and validate a data-driven approach for built environment quality evaluation/validation based upon measurement of real-time emotional responses to simulated environments. This paper presents an experiment that was conducted by combining an immersive virtual environment (virtual reality) and electroencephalogram (EEG) as a tool to evaluate Pre and Post Purple Line development. More precisely, the objective was to (a) develop a data-driven approach for built environment quality evaluation and (b) understand the correlation between the built environment characters and emotional state. The preliminary validation of the proposed evaluation method identified discrepancies between traditional evaluation results and emotion response indications through EEG signals. The validation and findings have laid a foundation for further investigation of relations between people’s general cognitive and emotional responses in evaluating built environment quality and characters.