Systems and methods for property feature detection and extraction using digital images. The image sources could include aerial imagery, satellite imagery, ground-based imagery, imagery taken from unmanned aerial vehicles (UAVs), mobile device imagery, etc. The detected geometric property features could include tree canopy, pools and other bodies of water, concrete flatwork, landscaping classifications (gravel, grass, concrete, asphalt, etc.), trampolines, property structural features (structures, buildings, pergolas, gazebos, terraces, retaining walls, and fences), and sports courts. The system can automatically extract these features from images and can then project them into world coordinates relative to a known surface in world coordinates (e.g., from a digital terrain model).