This study addresses the importance of sustainable investment in urban heritage sites as a pathway to economic, social, and cultural development. It aims to analyze and assess various international and regional experiences, including those of Jordan, Morocco, and Italy, to derive lessons that support the sustainability of heritage sites. The study employs a comparative analytical methodology to examine factors impacting investment in urban heritage sites. These factors include strategic, legal, organizational, administrative, economic, social, cultural, and technical aspects, contributing to a comprehensive evaluation of the effectiveness of sustainable investments. This study highlights the significance of engaging local communities as a cornerstone of conservation efforts and activating cultural policies to enhance heritage awareness. It also examines the role of international charters and their diverse applications in supporting investment programs, providing a practical framework for both local and global policies to aid in sustaining these sites. The findings suggest that urban heritage sustainability requires an organized legal framework with local regulations aligned with international charters, along with governmental and financial support to foster public-private partnerships. The research recommends adopting advanced technical practices and methodologies to preserve the historical character of heritage sites while promoting cultural awareness to ensure sustained community engagement. Additionally, it proposes recommendations to enhance sustainable investment mechanisms, including fostering community participation, developing long-term strategic plans, and stimulating the local economy by repurposing heritage buildings to support cultural tourism and sustainable investment. These actions contribute to comprehensive and sustainable development.