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This case study examines the land and property market constraints in Addis Ababa, focusing on both supply- and demand-side issues. The assessment evaluates land-related policies, institutional frameworks, and urban land management practices at the federal and city levels. Key findings highlight challenges such as a lack of clear regulations, inadequate institutional capacity, limited land supply, and low private sector participation. The city faces significant issues related to expropriation laws, inefficient land administration, outdated land valuation systems, and informal market expansion. High demand for residential and commercial land further exacerbates these constraints, leading to increased land prices and limited access to finance. Using qualitative and quantitative methods, the study collected data through interviews, policy reviews, and geospatial analysis. The findings emphasize the urgent need for institutional reforms, enhanced regulatory frameworks, and improved transparency in land allocation and management. Recommendations aim to foster sustainable urban development and address the challenges faced by Addis Ababa’s growing population and economy.