A computer vision system and method for detecting and modeling features of a building in a plurality of images is provided. The system includes at least one computer system in communication with a database of aerial imagery, and computer vision system code executed by the at last one computer system which automatically detects contours and infers interior roof features of the building. The system first processes the plurality of images to identify a plurality of two-dimensional (2D) line segments in each image. Then, the system processes the plurality of 2D line segments to generate a plurality of three-dimensional (3D) line segments. The plurality of 2D line segments are then processed to detect a contour of the structure, and the contour of the structure is utilized by the system to infer interior roof lines from the structure. A model of the roof of the structure is finally generated using the detected contour and interior roof lines. The system can execute a straight-skeleton algorithm to infer the interior roof lines from the detected contour. Additionally, the system can detect roof rakes from the images.