Accurate loss assessment plays a vital role in understanding the economic risk of natural hazards, for planning, mitigation, and actuarial purposes. Because of its juggernaut status as the most widespread and costly hazard, both nationally and around the world, loss assessment due to flood is particularly important. One of the shortcomings in existing flood loss models is to partition the structure (or building) economic value of loss into that borne by the homeowner and that covered by flood insurance. The goal of this research is to model the loss incurred by the homeowner and that incurred by the National Flood Insurance Program, considering flood damage, building replacement value, flood insurance coverage amount, deductible, and flood characteristics (slope and y-intercept of the loss vs. return period curve). A Monte Carlo approach is used to calculate the annual average loss due to flood at the individual homeowner scale. Multiple linear regression (MLR) and Classification and Regression Tree (CART) models are trained to provide the output of the owner’s share of the loss. The CART model outperformed the MLR model with lower RMSE and MSE values and a higher R² value (0.95) on the test data set. Because out-of-pocket expenses due to flood can be devastating to financial security, the results of this study support and inform the proactive decision-making process that homeowners can use to self-assess their degree of preparation and vulnerability to the flood hazard.