This paper assesses the damage to high-set rectangular-plan houses with low-pitch gable roofs (built in the 1960 and 70s in the northern parts of Australia) to wind speeds experienced in tropical cyclones. The study estimates the likely failure mode and percentage of failure for a representative proportion of houses with increasing wind speed. Structural reliability concepts are used to determine the levels of damage. The wind load and the component connection strengths are treated as random variables with log-normal distributions. These variables are derived from experiments, structural analysis, damage investigations and experience. This study also incorporates progressive failures and considers the inter-dependency between the structural components in the house, when estimating the types and percentages of the overall failures in the population of these houses. The progressively increasing percentage of houses being subjected to high internal pressures resulting from damage to the envelope is considered. Results from this study also compare favourably with levels of damage and related modes of failure for high-set houses observed in post-cyclone damage surveys.