This study aimed to identify the perceived advantages and drawbacks of teleworking and their correlates, including health problems, among Lebanese workers holding a university degree. A web-based cross-sectional self-report questionnaire created on Google Forms was used to survey 230 participants through snowball sampling between October 2022 and March 2023. The majority of respondents recognized both the advantages (67.03%) and drawbacks (66.34%) associated with teleworking, suggesting mixed feelings toward this format. Despite the limited satisfaction with teleworking, respondents acknowledged the advantages associated with remote working; in particular, younger, less physically active, and more educated participants valued teleworking more than their counterparts. The mean perception of advantages and drawbacks of telework did not significantly change with participants’ work status (hybrid, online, and in-person). The study revealed a high prevalence of consistent sleeping difficulty (35.7%), limited regular physical activity (60.4%), work-related musculoskeletal disorders (48.7%), back pain (5.7%), and visual disorders (48%) among Lebanese workers. Despite the limited satisfaction with teleworking, respondents acknowledged advantages such as cost and time savings. Older workers showed a preference against teleworking, potentially due to its impact on well-being. Factors such as education, career satisfaction, and prior teleworking experience influenced individuals’ perceptions of telework benefits.