Machine learning systems, methods, and techniques for detecting damage and/or other conditions associated with a building, land, structure, or other real property using a real property monitoring system are disclosed. The property monitoring system is used in conjunction with machine learning techniques to determine and/or predict various conditions associated with the real property, including particular damage thereto, e.g., based upon dynamic characteristic data obtained via on-site sensors, static characteristic data, third-party input descriptive of an event impacting the building, etc. Accordingly, damage and/or loss associated with the building/real property is more quickly and/or accurately ascertained so that suitable mitigation techniques may be applied. In some scenarios, previously undetectable or uncharacterized damage and/or other conditions may be discovered and mitigated.