According to the latest 2021 Demographia International Housing Affordability Survey, Hong Kong continues to top the world's 92 metropolitan housing markets as the least affordable. Its house price-to-income ratio is 20.7, compared to Singapore's 4.7. Despite lengthy debates over the past decade, with various attempts to manage demand and increase land supply, and recent urge by the Central Government to have the problem tackled with determination, housing affordability remains lagging seriously behind needs and expectations. Is it just a land problem? What about planning restrictions and community politics? Can Hong Kong learn from Singapore? This policy dialogue re-examines these critical questions, with some insight from the Singapore experience.