This study investigated the impact of stay-at-home orders on depressive symptoms among community-dwelling older adults during the early stages of the COVID-19 pandemic. A questionnaire was administered to older adults living in Ayase City, Kanagawa Prefecture, in July 2020, after the Japanese government declared its first COVID-19 state of emergency and stay-at-home order. In a sample of 1056 people, 69.1% were stay-at-home, and 30.9% were not. Those in the first group were more likely to be women, young-old, or non-workers. In addition, the patients tended to have more diseases. Of the participants, 39.3% had depressive symptoms and 60.7% did not. Multivariate analysis revealed that depressive symptoms were associated with increased frequency of being alone during the daytime (OR = 1.27; 95% CI = 1.07, 1.51), less face-to-face contact with friends or acquaintances (OR = 0.78; 95% CI = 0.65, 0.94), increased contact with friends or acquaintances through email/LINE app (OR = 1.29; 95% CI = 1.03, 1.60), and refraining from going out (OR = 1.54; 95% CI = 1.12, 2.09). These results suggest that quarantine measures related to soft lockdowns may aggravate the mental health of community-dwelling older adults. Therefore, it is necessary to consider macro-level policies.