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In the last twenty-five years, financial transactions have increasingly come under scrutiny for connection to money laundering and terrorist financing; in Canada as in the United States and other OECD nations, individuals working in specific industries in the private sector must examine financial transactions to ensure that they are not facilitating the financing of terror, economic crimes, or the work of criminal groups. In real estate, as in banking, insurance, or other cash-intensive industries, those individuals conducting transactions on behalf of clients must report any suspicious activity to their national anti-money laundering and counter-terrorist financing body. Little criminological research has been conducted into this topic. In this paper I will explore the reporting practices of real estate agents. Recent regulatory crackdowns in the US suggest that the real estate industry is an area of particular concern, yet there is a dearth of information regarding the policing practices of real estate agents and brokers. In this paper I explore the risk-based decision-making practices institutionalized in real estate regulations in Canada in order to understand how responsibilized individuals engage with these laws and determine whether a client might be laundering money or facilitating terrorism.