This study examined the educational significance of an intergenerational art appreciation program connecting schools and the local community. Adopting a qualitative case-study approach and the constant comparative method, it analyzed how shared practices of observing and dialoguing about artworks shaped the intergenerational and core art competencies of participants spanning diverse age groups, from children to seniors. The findings indicate that observation-based dialogue enabled participants to recognize complementary generational perspectives, fostering intergenerational understanding, empathy, communication, and collaboration. Through this process, participants reflected on their own interpretive habits and life contexts, leading to a renewed sense of identity and community. These relational experiences also facilitated the development of aesthetic sensitivity and creative-integrative thinking. Overall, this study suggests that art appreciation functions as a reciprocal educational mediator that simultaneously fosters identity formation, community building, and intergenerational integration within community-based art education.