After assessing the current state of maintenance, performed primarily by residents, of traditional wooden houses along major streets, we examined the challenges for maintaining such wooden houses in the future, taking the streetscape into account. Residents work regularly and continually to keep their houses in good condition. To ensure that they can live in the house for a long time, they carry out repairs and improvements and take measures to prevent or retard deterioration of parts and materials. In this way, the continuity of occupation is maintained. Survey responses show that many residents incorporate regular home care as part of their daily schedule. On the other hand, the attitudes of residents regarding maintenance have changed over the years due to factors such as changes in family structure, aging of residents, and feelings regarding streetscapes and neighborhoods. Awareness of the need for maintenance and the importance of its continuity are required since it is connected to regular home care. It is also necessary to consider the long-term, not simply maintaining the house as a building, but also preserving tradition by adapting the feelings of family and past generations to contemporary life. Further study is needed on ways to facilitate not only self-help, but also cooperative and public assistance.