Sustainability of settlement systems is of greatest relevance in political and socio-economic stability all over the world. The development effectiveness of a rural settlement system involves the solution of a number of matters in sustainable development, namely social welfare and environmental balance, economy and industry development, improving the pipeline and utility infrastructure, and improving the efficiency of the decision-making process. Currently, the sustainability of a rural settlement system is one of the key objectives in regional planning in post-Soviet countries. The introduction of new tools for assessing and managing the settlement system development is particularly true for Belarus, as a country with a strong focus on agricultural industry. The research aim was to develop and approve a model for evaluating the settlement system development. The research methods were based on the complex and interdisciplinary approaches, namely the system-element approach, the comparative analysis, spatial and mathematical modelling, factor analysis, and the cartographic analysis. The model was approved by practical consideration for evaluating the development of the analogue object at the local planning level. The practical relevance of the research is associated with the potential for using the model as a significant tool in land use planning. The model employs both quantitative and qualitative evaluation to obtain alternative solutions towards sustainable development of rural areas. Another advantage of the model is its multifunctionality, which enables: (1) sustainability evaluation of a settlement system, (2) establishment of regional planning priority areas, and (3) development of specific measures for ensuring the sustainability of a regional settlement system and its elements.