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This Note will use the Hamilton Farm incident in Winchester, Massachusetts, to discuss the effects and inefficacy of Chapter 40B.30 Part II, sections A and B, will first explore the history, usage, and contours of Chapter 40B. Part II, sections C and D, will then address the law as applied to Winchester, Massachusetts, including the motivations behind Winchester’s resistance to the proposed development of Hamilton Farm and the scheme Winchester took to avoid the law. Next, section D will introduce the Massachusetts General Laws Chapter 40R (Chapter 40R) Smart Growth Zoning and Housing Production law as an alternative to Chapter 40B. Part III will argue that Chapter 40B was, indeed, successful in motivating Winchester residents to implement more inclusive zoning laws, even though the law was not able to create affordable housing in this instance. Finally, this Note will conclude that Chapter 40B is not the most efficient means to achieve Massachusetts’s affordable housing goals despite the legislature’s admirable intentions.