Problem setting. Ukraine and Estonia have a very rich common history. Especially regarding law. Let us note three, as we can see, significant aspects, firstly, the law of each of these states was influenced by Roman law, secondly, both states were part of a totalitarian state and the legal system corresponding to it for 70 years, thirdly, Estonia is a member state of the European Union, and Ukraine is a candidate for joining the European Union, which, in turn, affects the legal systems of both of these states. It is also important to consider that active bilateral relations have formed between our state and Estonia. For example, the Government of Ukraine and the Government of the Republic of Estonia signed the Convention on the Avoidance of Double Taxation and the Prevention of Tax Evasion Regarding Taxes on Income and Property, the Agreement between the State Tax Administration of Ukraine and the Estonian National Tax Service on Mutual Administrative Assistance, the Agreement on Technical Cooperation between the DPA of Ukraine and Tax and Customs Board of Estonia. Therefore, conducting a comparative characterization of taxation of income received from independent professional activity is relevant. Analysis of recent researches and publications. The issue of taxation of income received from independent professional activity in Ukraine is one of the controversial ones, as evidenced by numerous publications by scientists (E.V. Postoronko). What was emphasized in the previous works is also confirmed by established judicial practice, active discussion among scientists, etc. Target of the research is to conduct a comparative analysis of the legal regulation of taxation of income received from independent professional activity in Ukraine and Estonia, to carry out a comparative characterization of it. Article’s main body. The article analyzes and compares the legal regulation of taxation of income received from independent professional activity in Ukraine and Estonia. The issue of taxation of income received from independent professional activity in Ukraine is one of the controversial ones, as evidenced by numerous publications by scientists. It was established that currently the Tax Code of Ukraine enshrines such a category of taxpayers as a self-employed person. In Ukraine, the concept of “self-employed person” is used, which in its meaning covers two types of payers: an individual entrepreneur and an individual engaged in independent professional activity, whereas in Estonia we are talking about an entrepreneur an individual (depending on the translation, the concept is used: “ self-employed person”, “entrepreneur natural person”, “individual entrepreneur”), who can carry out economic or professional activity, but in any case professional activity refers to entrepreneurial activity. It is noted that natural persons engaged in independent professional activity in Ukraine pay personal income tax, military service and, along with this, a single social contribution for mandatory state insurance. In Estonia, in their turn, the same taxpayers pay: income tax, social tax, mandatory accumulated pension contribution, unemployment insurance payment. Conclusions and prospects for the development. The conducted comparative characteristics made it possible to focus on the common and the different. It is especially worth paying attention to the fact that the activity of natural persons who are not employees within the scope of their activity is considered entrepreneurial in Estonia, both economic and professional. This approach is considered simple, clear and avoids the imbalance of public and private interests, restrictions and discrimination of taxpayers. Therefore, we consider the experience of Estonia in terms of recognizing independent professional activity as entrepreneurial to be progressive and such that it can be applied in Ukraine