The main purpose of current research was to investigate the impact of self-rated metacognitive measures and depressive symptoms in predicting psychological well-being in different aged healthy adults. A further goal was to explore the effect of genre and age on metacognition and depression scores. Ninety-six healthy adults were, respectively, assigned to young (i.e., 20–30 years), old (i.e., 65–74 years), very old (i.e., 75–84 years), and oldest old (i.e., >85 years) groups. Participants were administered self-referent social desirability, cognitive efficiency, subjective wellness, and psychological distress questionnaires. It was found that social desirability, depression, cognitive functioning, and metamnestic scores represent the best predictors of well-being. Moreover, a significant main effect of age and genre was found on measures of depression and metamemory. Finally, personal satisfaction, coping strategies, emotional control, and general well-being levels of the very old group did not reach critical cutoff for the Italian octogenarian population.