Two sets of data, each containing property listings, are obtained from two discrete merchant platforms. Each property listing in a set of data of a first merchant is sequentially paired with each of the property listings in a set of data of a second merchant. For each pair, each image of the property listing of the first merchant is compared to each image of the property listing of the second merchant, and images of statistically sufficient similarity are identified. The similarity of images, and in particular, of similar images likely to be rooms of the property, are considered in a determination of whether the product listings of the first and second merchant are for the same cross-listed product.