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Smart City is about incorporating ‘Smart Thinking’ in the city’s urban design and planning with a focus on People Place and Planet. This chapter will explore how Smart and Sustainable Living is achieved when applying ‘Smart Thinking’ to the city’s development with Hong Kong as the case study. Housing affordability, open space provision, and cultural heritage preservation will be studied and analysed to understand their impact on the quality of living. The various initiatives from public, private, institutional, academic and community will provide a better understanding of Hong Kong’s recent efforts in creating a smart and sustainable city. This chapter enables us to conclude with the overall quality and future positioning of the city’s living environment in achieving a smart and sustainable Hong Kong.