The accelerated densification of Western European cities driven by economic growth has major spatial implications for their overall livability. Often, new homes must be built within an existing urban fabric, creating higher density environments. However, the impact on the experience of these high-density environments at eye level remains unstudied and unknown. This chapter reviews two experiments that sought to understand the unconscious reception of streetscapes using eye-tracking technology to investigate the sequence of users’ (visual) experience, their behavior and perception. The research project seeks to establish more ‘evidence-based’ design guidelines for streetscapes in high-rise urban settings.