A healthy school environment is an important element of the Coordinated School Health model, which periodically focuses on the quality of a school’s physical and esthetic surroundings as well as its psychosocial climate, safety, and culture. According to previous studies, the characteristics of a school environment are statistically related to the students’ health and academic achievement. Therefore, the purpose of this paper is to examine various aspects of a school environment, their influences on the well-being of the school community, and the need for improvements. A comprehensive study on school health promotion was conducted with a representative sample of schools in the region of Pleven, Bulgaria. Data were collected by means of a self-administered questionnaire among students, parents, and staff as well as through interviews with school principals. In the region of Pleven, there are a total of 118 schools, which were built between 1912 and 1998. The majority of the buildings have been renovated, and the school surroundings are generally well-maintained. However, approximately 60% of the buildings have no easy access for disabled persons, and according to the school documents, any deviations from the standards of temperature, lighting, and ventilation in the classrooms have not been registered. In addition, approximately 40% of the respondents felt that improvements in human relationships and job satisfaction would create a healthier school community. Based on the findings, the influence of a healthy school environment on the welfare and academic performance of students and staff is confirmed and such an environment should be a precondition for the welfare of other school communities.