Over the past 15 years, Singapore’s real estate agency industry has been transformed by regulation, technology, digital listing platforms, and changing consumer expectations. Revisiting the Structure–Conduct–Performance (SCP) framework, this article examines how the competitive landscape evolved between 2011 and 2026, and what these changes mean for property agents, buyers, sellers, and investors. Drawing on the firsthand experience of a practising Key Executive Officer (KEO), it offers an insider’s perspective on one of the most significant periods of change in the industry’s history.