Floods are consistently ranked as the most financially devastating natural disasters worldwide. Recent flood events in the Netherlands, Caribbean, and US have drawn attention to flood risks resulting from pluvial and fluvial sources. Despite shared experiences with flooding, these regions employ distinct approaches and flood management strategies due to differences in governance and scale—offering a three-site case study comparison. A key, yet often lacking, factor for flood risk and damage assessments at the parcel level is building elevation compared to flood elevation. First-floor elevations (FFEs) are a critical element in the vulnerability of a building flooding. US-based flood insurance policies require FFEs; however, data availability limitations exist. Drone-based FFEs were measured in all locations to assess the flood vulnerabilities of structures. Flood vulnerability profiles revealed 64% of buildings were vulnerable to a form of inundation, with 40% belonging to “moderate” or “major” inundation, and inundation elevation means (IEMs) of −0.55 m, 0.19 m, and 0.71 m within the US, Netherlands, and Puerto Rico sites, respectively. Spatial statistics revealed FFEs were more responsible for flood vulnerabilities in the US site while topography was more responsible in the Netherlands and Puerto Rico sites. Additional findings in the Puerto Rico site reveal FFEs and next highest floor elevations (NHFEs) vulnerable to future sea level rise (SLR) flood elevations. The findings within the Netherlands provide support for developing novel multi-layered flood risk reduction strategies that include building elevation. We discuss future work recommendations and how the different sites could benefit significantly from strengthening FFE requirements.