Sustainable development of local heritage areas can boost the economy and people’s standard of living. This research describes transformational leadership contributing to the sustainable development of local heritage in Medan City and Semarang City. This research uses a descriptive qualitative method. Data were obtained by observation, documentation, and interviews. Data analysis techniques were used by reducing data, presenting, and making conclusions. The results showed that transformational leadership contributes to the development of sustainable development of the Kesawan area in Medan City and the Kota Lama area in Semarang City, which is seen based on four characteristics of transformational leadership, namely: idealistic leadership, inspirational motivation, intellectual stimulation, and individualized consideration. Medan City has potential as the condition of the building is still very good in the Kesawan area. The obstacles are the legal aspects where many illegal buildings are built and the need for coordination between the government and non-government organizations. In Semarang City, the driving factor is more influenced by the government’s and stakeholders’ readiness and awareness regarding the Kota Lama Area as a cultural heritage. Barriers regarding the level of security and bureaucracy over the massive turnover of members who have the authority to continue the management of the Kota Lama. From the Implementation results, Medan City is still in revitalization and infrastructure development, so the results must be concrete and specific. On the other hand, the Semarang City Government has provided concrete and specific contributions, especially in economic and socio-cultural aspects.