Provided are an information processing system and an information processing method with which real estate property information can be provided favorably in accordance with image content. Included are means for managing a plurality of images relating to a real estate property together with image evaluation information that represents objects shown on the images and is attached thereto using a first evaluation model generated by machine learning, means for managing entry evaluation values that relate to entries respectively representing a plurality of real estate properties, and are calculated using one or more pieces of the image evaluation information associated with each of the plurality of real estate properties, and means for outputting a list of the entries relating to the plurality of real estate properties, an order of the entries on the list being determined in accordance with the entry evaluation values.