A property video listing system is provided including an Internet connected server configured to : provide a website for receiving a plurality of video files from a user to upload in association with a property listing; upload all of the received video files to a video hosting service while providing identifying data with each uploaded video file; and display the property listing and provide thumbnail photos with links to each of the uploaded video files whereby visitors of the website may view the video files within the pro perty listing. Alternatively/additionally the server may : identify each thumbnail photo by one of a plurality of different feature designations; track access by visitors of each of the video files; and generate reports of relative interest in each property listing by th e visitors as a function of an extent of access by the visitors of the video files associated with each property listing.