Changes in the modern paradigm of ecological thinking require a significant reorganization of logistics processes and the need to transform logistics systems in the context of the concepts of green economy. In view of this, the purpose of this paper is the further development of theoretical and methodological provisions and justification of the feasibility of applying a comprehensive approach to green investment in logistics systems development, taking into account modern global environmental challenges and threats. To achieve the aim of the research, the following scientific methods were used: analysis, synthesis, induction, deduction, observation, comparison, formalization, classification, expert evaluations, statistical analysis, and structural and logical generalization. The article clarifies the meaning of the concepts “sustainable financing”, “green investments”, and “green bonds” from the standpoint of logistics systems development. A systematic approach to evaluating the effectiveness of the logistics systems development in the countries of the world is proposed. The key shortcomings of the existing methods of evaluating the logistics systems development have been revealed. A comparative analysis of indicators characterizing the current state of operation of the logistics system using the example of the United Kingdom, Poland and Ukraine was performed. The expediency of applying a comprehensive approach to sustainable financing of the logistics systems development is substantiated, the essence of which is the integration of the main components of the organizational and economic mechanism (principles, functions, management methods, information systems and green technologies), green investment and insurance tools for the implementation of priority areas of green transformation of logistics systems.