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Road authorities worldwide can leverage the advances in vehicle technology by continuously monitoring their roads’ conditions to minimize road maintenance costs. The existing methods for carrying out road condition surveys involve manual observations using standard survey forms, performed by qualified personnel. These methods are expensive, time-consuming, infrequent, and can hardly provide real-time information. Some automated approaches also exist but are very expensive since they require special vehicles equipped with computing devices and sensors for data collection and processing. This research aims to leverage the advances in vehicle technology in providing a cheap and real-time approach to carry out road condition monitoring (RCM). This study developed a deep learning model using the You Only Look Once, Version 5 (YOLOv5) algorithm that was trained to capture and categorize flexible pavement distresses (FPD) and reached 95% precision, 93.4% recall, and 97.2% mean Average Precision. Using vehicle built-in cameras and GPS sensors, these distresses were detected, images were captured, and locations were recorded. This was validated on campus roads and parking lots using a car featured with a built-in camera and GPS. The vehicles’ built-in technologies provided a more cost-effective and efficient road condition monitoring approach that could also provide real-time road conditions.