The Sarasota County School Building Program 1955-1960 is revisited through a detailed examination of how architects and educators collaborated to design an innovative group of public schools that provided opportunities for the transformation of learning space. This multi-dimensioned examination is grounded in an historical contextualization of the school building program; in visual and discursive archival analysis related to four of the schools considered especially notable; and in the integration of contemporary voices of some of the teachers, students, and educational employees who worked in these schools. A concluding section discusses four key lessons of this artistic-educational collaboration that might be fruitful for educators to ponder as they seek to create the kinds of learning environments that optimize students’ educational experience.