We investigated the relationship of edentulousness, dental health, and dental health behavior to depressive symptoms in the 55-year-old population of Oulu (a medium-sized Finnish town), 780 of whom (78%) participated. The dental examination included an assessment of oral health status. Depressive symptoms were determined with the Zung Self-Rating Depression Scale (ZSDS). The participants were also asked about their dental health behavior, smoking habits, health, life satisfaction, and factors related to their work. Depressive symptoms were associated with edentulousness among non-smoker men. When further evaluated by logistic regression analysis, edentulousness was independently associated with depressive symptoms in this subpopulation (odds ratio = 6.4, confidence interval = 1.4–29.2) after adjusting for confounding factors. Depressive symptoms were not associated with dental caries, periodontal status, or number of teeth. The dentate women with high rates of depressive symptoms had a more negative attitude towards preserving their natural teeth, used sugary products more frequently, reported a longer time since their last dental visit, and tended to have a lower percentage of filled tooth surfaces than the non-depressed dentate women. The aspect of depression should be borne in mind by dentists when treating edentulous patients. On the other hand, certain subgroups of depressed patients might benefit from dental implant therapy. Thus, the importance of teamwork between clinicians, psychiatrists, and dentists is emphasized.