This paper presents the design and experimental validation of an On-Road Wireless EV Charging System integrated with Internet of Things (IoT) monitoring. The system embeds resonant inductive transmitter coils beneath road surfaces at high-dwell locations such as traffic intersections and toll plazas, enabling contactless energy transfer without mandatory vehicle downtime. An ESP32-based edge controller manages closed-loop power regulation and RFID-based vehicle authentication, while a Firebase cloud backend and Flask web dashboard deliver real-time telemetry, session management, and automated billing. Experimental results confirm a DC-to-DC transfer efficiency of 83.2% at a 10 mm air gap and energy metering accuracy within ±1.4% of reference instruments. The system successfully passed all functional test cases including cloud synchronization, fault detection, and session deduplication, demonstrating a viable path toward eliminating range anxiety in urban EV ecosystems.