The closure of schools due to the COVID-19 pandemic has forced adolescents to stay home. These disruptions, as well as a significant decrease in social access, have impacted smoking behavior. This study identified the association between the adolescents’ type of residence and tobacco product use. A cross-sectional study (using data from the Korea Youth Risk Behavior Web-based Survey) examined 3774 students in 2019 (pre-pandemic) and 2575 students in 2020 (during the pandemic). The participants were South Korean middle and high school students aged 13–19 years. Using multinomial logistic regression, it was shown that adolescents who lived alone or in a boarding house had a higher risk of being an e-cigarette smoker compared with those who lived with family or relatives (OR = 6.49, CI = 2.06–20.45). Living in a dormitory or orphanage also increased the risk of dual tobacco use compared with living with family (OR = 2.09, 95% CI = 1.13–3.84). With the advent and continuation of the COVID-19 pandemic, this effect became more significant in 2020 than in 2019. Our findings support the theory that residential differences affect adolescent smoking behavior and highlight the importance of integrated smoking bans and educational programs to control adolescent smoking.