After a large-scale disaster, many damaged buildings are demolished and treated as disaster waste. Though the weight of disaster waste was estimated two months after the 2016 earthquake in Kumamoto, Japan, the estimated weight was significantly different from the result when the disaster waste disposal was completed in March 2018. The amount of disaster waste generated is able to be estimated by an equation by multiplying the total number of severely damaged and partially damaged buildings by the coefficient of generated weight per building. We suppose that the amount of disaster waste would be affected by the conditions of demolished buildings, namely, the areas and typologies of building structures, but this has not yet been clarified. Therefore, in this study, we aimed to use geographic information system (GIS) map data to create a time series GIS map dataset with labels of demolished and remaining buildings in Mashiki town for the two-year period prior to the completion of the disaster waste disposal. We used OpenStreetMap (OSM) data as the base data and time series SPOT images observed in the two years following the Kumamoto earthquake to label all demolished and remaining buildings in the GIS map dataset. To effectively label the approximately 16,000 buildings in Mashiki town, we calculated an indicator that shows the possibility of the buildings to be classified as the remaining and demolished buildings from a change of brightness in SPOT images. We classified 5701 demolished buildings from 16,106 buildings, as of March 2018, by visual interpretation of the SPOT and Pleiades images with reference to this indicator. We verified that the number of demolished buildings was almost the same as the number reported by Mashiki municipality. Moreover, we assessed the accuracy of our proposed method: The F-measure was higher than 0.9 using the training dataset, which was verified by a field survey and visual interpretation, and included the labels of the 55 demolished and 55 remaining buildings. We also assessed the accuracy of the proposed method by applying it to all the labels in the OSM dataset, but the F-measure was 0.579. If we applied test data including balanced labels of the other 100 demolished and 100 remaining buildings, which were other than the training data, the F-measure was 0.790 calculated from the SPOT image of 25 March 2018. Our proposed method performed better for the balanced classification but not for imbalanced classification. We studied the examples of image characteristics of correct and incorrect estimation by thresholding the indicator.