The issues we face, such as climate change, call for the transformation of our society. It is important for schools to become agents of transformation and for school members to build capacity for transformation. However, it is not easy for education toward transformation and sustainability to be mainstreamed in schools. This study conducted a case study of A Middle School, which has been engaged in meaningful educational practices through a whole school approach. ENSI’s Quality Criteria for Education for Sustaianable Development schools and the whole school approach pentagon (WSAP) model as a framework to describe the constituent areas of the whole school approach. The analysis and description included a review of the school education plans and related literatures, and interviews with a teacher from Middle School A and a representative from the neighboring B village. First, at the level of school operations and decision-making, there is governance, with teachers and social cooperatives at the center. Village and democracy are also two pillars of the curriculum. Starting with the “Village is the School” curriculum in the early days of the Innovation School, “Community Living Agreement”, “Ecology and Energy”, and “Cooperatives” became the main curriculum topics. In recent years, the curriculum has also included the Sunlight School Project, ecological transformation education, and climate and energy conergence curriculum, which are often loosely integrated with other subjects and carried out in collaboration with the village. Many diverse and innovative pedagogies are found in the teaching and learning process, and students’ real lives, schools, and villages are often used as contexts. The management and operation of school facilities are centered around the zero-energy house and solar power plant. Students, teachers, and villagers are involved in the creation and operation of these facilities, and they are based on community partnerships. At the center of all of these activities are various “curricula”, which are based on the social learning of school members and villages. Village and democracy are key themes, and are based on a working partnership between school and village. The whole school approach to sustainable society in this school corresponds to the highest stage of the developmental stages proposed in the previous research namely stage 4, the transformational stage. It can be said that the school is creating a transformation of schooling and a transformation of the community through a whole school approach, which provides meaningful implications for many schools attempting to implement a whole school approach to sustainability.