This study aims to describe the management strategy of waqf-based Pesantren applied by Pondok Modern Darussalam Gontor (PMDG) in developing human capital and entrepreneurship education. It uses qualitative descriptive methods. The data were collected through observation, interview, and documentation, and then processed through triangulation techniques. The result shows that waqf-based pesantren strategies aimed to develop human capital and entrepreneurship Education is implemented through community-based education (Kiai, teachers, santri, and society). This strategy makes pesantren as a medium of learning combined with the internalization of islamic, cultural, and philosophical values, leadership and strengthening of modern management systems in order to create quality generations embedded 3 intelligences including iman (faith), ilmu (knowledge), and amal (good deed).The implication of this study is to make better management of waqf in waqf-based educational institutions, and invite them to make the strategy as an instrument to develop and improve the accountability of waqf management to stakeholders.