Telecommuting has reached unprecedented levels in Japan, previously established due to the sudden outbreak of the COVID-19 pandemic; however, there is a lack of in-depth research on telecommuting frequency from the perspective of the post-pandemic era. Hence, this study investigated the relationship between employees’ expected levels of telecommuting allowed by the company and their preferred telecommuting frequency after the pandemic using an ordered response probit model with a correlation effect. Data were collected through an online questionnaire in three major metropolitan areas of Japan; the questionnaire included questions on sociodemographic, commuting, household, and work-related characteristics. The findings revealed that work-environment characteristics are prime factors influencing both expected and preferred telecommuting frequency; therefore, a telecommuting-oriented work environment is crucial for bridging the gap between employees and employers regarding telecommuting. Also, the results indicated that the preferred level of telecommuting is unattainable probably due to a lack of support from the company. Finally, a gap was identified between the expected telecommuting frequency that companies would allow and the preferred telecommuting frequency. This study provides implementations to achieve a work environment better adapted to the post-pandemic era and contributes to the establishment of future traffic forecasting models that enable effective mobility management through telecommuting.