In Jamaica, schools are placed in six regions which involve one to three parishes, but in one instance, two regions are partially located in one parish. While schools in any jurisdiction should perform in accordance with stated standards and established criteria, there are many factors which seem to mitigate against this expectation. This failure usually results in weaker schools located in some regions whose performance differ based on factors such as location-urban versus rural, the levels and types of schools, the overall population of these schools, and quality of human resources, including teachers and principals, among others. In Jamaica, Region 1 comprises three adjoining parishes, Kingston, St. Andrew and St. Thomas. Five of the regions are essentially in rural Jamaica, except region 1 and even then substantial parts of St. Andrew are rural and St. Thomas is fully rural. The fact that schools are located in mainly rural settings means that the leadership displayed by the principal will be influenced by the given context and his/her ability to use personal abilities and characteristics to influence change. This study seeks to determine if school constituents' ratings of the leadership dimensions of high-performing principals based on the regional location of schools. A knowledge of the ratings of high-performing principals is important because the leadership provided by the principal is central to school performance generally. This paper locates the study of high-performing principal in the Jamaican school context and provides a review of the relevant literature with emphasis on the phases of leadership development and the four dimensions related to the performance of high-performing principals. The overview of the methodology presents the sample, procedures and statistical tests which were used and the findings presented and discussed in regards to the four dimensions related to the performance of high-performing principals. The conclusion makes specific suggestions and recommendations regarding strategies and approaches to address some of the problems related to the differences in the ratings of the performance dimensions of high-performing principals based on school regions.