In this article, Kevin M. Kane, Karen Hunter Quartz, and Lindsey T. Kunisaki describe the transformative parent engagement fostered in a multigenerational afterschool arts program at a community school. Community schools bring together families, teachers, and other neighborhood partners to help students learn, grow, and thrive and often integrate health, education, and social services. This embedded case study shows how community schools can also nurture cultural assets in the form of parents' community cultural wealth. The learning of these community school parents demonstrates the mutually reinforcing relationships between transformative parent engagement, collaborative leadership, expanded learning opportunities, and integrated student supports. This study highlights the transformative impact of culturally sustaining arts on individuals, families, and the school as a whole, offering implications for researchers and practitioners in community-based arts education and community school development.