As ‘gatekeepers’ to the financial system, lawyers, accountants and real estate agents play an indispensible role, intentionally or unwittingly, when criminals use their services to facilitate real estate transactions with illicit funds. Recognised as a high-risk, high-value sector for money laundering, empirical research in this area is, however, scarce. The important question then becomes how effective is the policy objective to detect and deter money laundering through professional facilitators in the real estate market? This thesis answers that question with new empirical evidence drawn from New Zealand criminal proceeds real estate transactions facilitated by professionals. Unlike other countries where professionals are partly or wholly exempt from anti-money laundering regulations, obligations to detect and report suspicious real estate transactions have applied to professional facilitators in New Zealand since 1996, yet inexplicably there is almost no objective evidence in this area. This thesis uses primary sources including court records to fill a knowledge gap in the use of professionals enabling financial transactions with illicit funds. It concludes that policies to detect and deter laundering through professional facilitators achieved intended outcomes in just four percent of research cases over a 20-year period. It found that when presented with property transactions involving proceeds of crime, professionals were more often enablers than inhibitors.