A stochastic model for predicting wind-induced damage to wooden houses in snowy cold region has been developed, focusing on roofs. The model consists of ‘wind loading model’ and ‘wind resistance model’. These models consider the regional features of the structures and the aged deterioration of the roofing. The evaluation methods of the wind resistant performance and the wind load acting on the roofing are based on the building code and previous studies. Furthermore, pulling-up load test was carried out to evaluate the wind-resistant performance of roof frame joints. It is found that the materials and construction of roofs commonly used in snowy cold regions tend to cause much wind damage to roofing and roof structures. The results of a probabilistic analysis of the damage indicate that damage to roofs can be reduced significantly by appropriate maintenance.