This systematic review and meta-analysis examined whether and how music listening impacts cognition and affect in healthy older adults, specifically considering the emotional connotations of music (happy- or sad-sounding music) and its presentation modality (background or prior to the tasks). Based on the PRISMA guidelines and preregistering in PROSPERO (CRD42022366520), we searched the Scopus, PsycInfo, and Web of Science databases. Out of 2,675 articles, 27 met the inclusion criteria. The synthesized findings on cognition (23 studies) revealed an uncertain influence of music type and presentation modalities on memory outcomes. In contrast, happy-sounding music seems to support executive functioning (2 out of 4) and processing speed (1), when presented in the background, and facilitate language processes (2 out of 3), when given prior to the task. However, the high heterogeneity and inconsistency in the music type and presentation modalities, as well as in the cognitive outcomes considered, prevented us from drawing clear conclusions on the effect of music listening on older adults’ cognition. For affective outcomes, a narrative synthesis of the findings on mood (12 studies) and arousal (7 studies) outcomes showed that, regardless of music presentation modality, happy- and sad-sounding music increase or decrease mood/valence and arousal, respectively. Results from meta-analysis showed no significant cognitive benefits from music listening (SMD = 0.09, [95% CI: −0.17, 0.35], p = 0.51) and suggest a positive effect of happy-sounding music on arousal (SMD = 0.44 [95% CI: 0.13, 0.74], p = 0.005), but not on valence (SMD = 0.79 [95% CI: −0.25, 1.84], p = 0.14). The methodological shortcomings of the extant literature call upon the need for further studies adopting more rigorous and consistent approaches that better elucidate the potential benefits of music listening on cognitive and affective outcomes among older adults.