Objectives: The work system reform and the COVID-19 pandemic in Japan have prompted efforts toward telecommuting in Japan. However, only a few studies have investigated the stress and health effects of telecommuting. Therefore, this study aimed to clarify the relationship between telecommuting and job stress among Japanese workers. Material and Methods: This was a cross-sectional study. In December 2020, during the “third wave” of the COVID-19 pandemic, an Internet-based nationwide health survey of 33 087 Japanese workers (The Collaborative Online Research on Novel-coronavirus and Work, CORoNaWork study) was conducted. Data of 27 036 individuals were included after excluding 6051 invalid responses. The authors analyzed a sample of 13 468 office workers from this database. The participants were classified into 4 groups according to their telecommuting frequency, while comparing scores on the subscale of the Job Content Questionnaire (JCQ) and subjective job stress between the high-frequency, medium-frequency, low-frequency, and non-telecommuters groups. A linear mixed model and an ordinal logistic regression analysis were used. Results: A significant difference in the job control scores of the JCQ among the 4 groups was found, after adjusting for multiple confounding factors. The high-frequency telecommuters group had the highest job control score. Further, after adjusting for multiple confounding factors, the subjective job stress scores of the high- and medium-frequency telecommuters groups were significantly lower than those of the non-telecommuters group. Conclusions: This study revealed that high-frequency telecommuting was associated with high job control and low subjective job stress. The widespread adoption of telecommuting as a countermeasure to the public health challenges associated with the COVID-19 pandemic may also have a positive impact on job stress. Int J Occup Med Environ Health. 2022;35(3):339–51