The system of financial monitoring establishes specifically designated entities on the real estate market. The assessment of a client’s risk of money laundering when entering into agreements in this market is a complex task and requires the development of new tools for implementing the risk-oriented approach, which is a priority in accordance with international standards in the financial monitoring system. The purpose of the study is to develop a risk-oriented approach to assessing the client and to develop practical recommendations for determining its level of risk in financial monitoring in the real estate market. To achieve a specific goal, a system of general scientific and special research methods, expert rankings and optimization modeling are used. On the basis of Methodical materials on financial monitoring issues for business entities, which provide services in the course of real estate purchase and sale operations, the points of client’s correspondence to high risk, which corresponds to the concept of developing a risk-oriented approach based on the main criteria of client risk assessment: geographic location of the state, client type and business relations. Taking into account the complexity of such assessment and the necessity of operative decision-making, a risk assessment rating (cost) scale has been developed for an integrated automated determination of a client’s risk level and an assessment of high-risk clients in the Decision Making Helper decision-making support system software on specific examples of legislation violations concerning the financial monitoring on the real estate market. The feasibility of implementing a new risk-oriented approach to assessing high-risk clients has been proved by automating the process of determining its level to reduce the time to decide on prevention and counteraction to the legalization of incomes and money laundering.