Dengue disease incidence is related with the construction of a house roof, which is an Aedes mosquito habitat. This study was conducted to classify pitch roof (PR) and flat roof (FR) surfaces using pan-sharpened Worldview 2 to identify dengue disease patterns (DDPs) and their association with DDP. A Supervised Minimum Distance classifier was applied to 653 training data from image object segmentations: PR (81 polygons), FR (50), and non-roof (NR) class (522). Ground validation of 272 pixels (52 for PR, 51 for FR, and 169 for NR) was done using a global positioning system (GPS) tool. Getis-Ord score pattern analysis was applied to 1154 dengue disease incidence with address-approach-based data with weighted temporal value of 28 days within a 1194 m spatial radius. We used ordinary least squares (OLS) and geographically weighted regression (GWR) to assess spatial association. Our findings showed 70.59% overall accuracy with a 0.51 Kappa coefficient of the roof classification images. Results show that DDPs were found in hotspot, random, and dispersed patterns. Smaller PR size and larger FR size showed some association with increasing DDP into more clusters (OLS: PR value = −0.27; FR = 0.04; R² = 0.076; GWR: R² = 0.76). The associations in hotspot patterns are stronger than in other patterns (GWR: R² in hotspot = 0.39, random = 0.37, dispersed = 0.23).