Road safety is key to sustainable mobility. Rapid technological advances have allowed several road safety-related analyses, previously performed in situ, to be conducted virtually. These virtual analyses benefit understanding of how roads operate and how users perceive them. Additionally, they facilitate the assessment of several parameters that are fundamental to road design and operation. The available sight distance (ASD) is one of these parameters that, if not provided adequately, could alter the proper functioning of roads. This study presents a framework to assess the impact of certain features on visibility. First, the ASD is estimated using a geographic information system (GIS)-based procedure with LiDAR-derived three-dimensional (3D) models. Afterward, obstructions are detected and categorized. If the obstruction cannot be removed, their redesign or relocation is simulated to re-run the analysis. These simulations are performed using 3D city objects, and their results are statistically evaluated, providing evidence as to their effects on visibility. The results proved that the procedure helped achieve the efficient use of roadside space, while including safety concerns. Additionally, this study reflects the need for more inspections on the impact of on-street parking on drivers’ fields of view.