Systems and methods for roof condition assessment from digital images using machine learning are disclosed, including receiving an image of a structure having roof characteristic(s), first pixel values depicting the structure, second pixel values outside of the structure depicting a background surrounding the structure, and first geolocation data; generating a synthetic shape image of the structure from the image using machine learning, including pixel values forming a synthetic outline shape, and having second geolocation data; mapping the synthetic shape onto the image, based on the first and second geolocation data, and changing the second pixel values so as to not depict the background; assessing roof characteristic(s) based on the first pixel values with a second machine learning algorithm resulting in a plurality of probabilities, each for a respective roof condition classification category, and determining a composite probability based upon the plurality of probabilities so as to classify the roof characteristic(s).