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This chapter explores adaptive reuse as a sustainable urban design strategy that balances heritage conservation with environmental and social needs. Using the National Urban Design Awards (NUDA) in Malaysia as context, it examines how emerging designers reimagine existing urban spaces into culturally rich and ecologically responsive environments. The study blends Shin's typological analysis with Li et al.'s Multi-Criteria Decision Model (MCDM) for both interpretive and evaluative depth. Grounded in theories by Rossi, Lynch, Jacobs, Gehl, Hillier, Yeang, and Bentley et al., it frames adaptive reuse as key to architectural sustainability in tropical cities. Findings show student proposals creatively reinterpret cultural memory and spatial potential, yet reveal gaps in policy and stewardship. The chapter concludes that adaptive reuse should be a core principle in sustainable urban transformation, linking education, practice, and civic policy.