Parking road vehicles is one of the most tedious and challenging tasks a human driver performs. Despite the low speeds involved, parking manoeuvres are among the main causes of minor and sometimes major traffic accidents, especially in urban areas where limited parking spaces are available. Furthermore, searching for a parking space wastes time and contributes to unnecessary road occupancy and pollution. This paper is dedicated to the development of an autonomous parking system for on-street parking in urban areas. The system is capable of fully automated parking manoeuvres from drop-off to pick-up zones, thus removing human drivers from the vehicle control loop. The system autonomously navigates to the parking space and parks the vehicle without human intervention. The proposed system incorporates a communication protocol that connects automated vehicles, parking infrastructure, and drivers. Several convenient human–machine interface concepts for efficient system communication and state monitoring have been developed. A methodology for validating the system in real time is proposed, which includes functionality requirements and a description of parallel and perpendicular parking manoeuvres. The proposed pipeline is tested on an electric vehicle platform with automated functions, where successful technological functionality is demonstrated.