This study aims to identify the success features and indicators of smart cities and real estate projects in order to increase their smartness and integration. Additionally, the study introduces a new comprehensive evaluation framework for both levels; this framework was developed by analyzing scientific literature, indexes, and relevant frameworks. The comparative benchmarks analysis demonstrated the practical application of the framework; seven benchmarks for each level were selected based on selection criteria. The framework is based on seven categories: smart governance, smart people, smart infrastructure, smart energy, smart environment, smart technology, and real estate status. The analysis revealed that cities and projects are adopting smart solutions with a significant integration between the chosen solutions. However, there is still room for improvement at both levels. The range of smart performance and indicators performance is illustrated in the study. The correlation analysis showed a significant correlation between the indicators. Smart real estate followed different strategies for integration into the smart city. Nevertheless, it was discovered that cities could limit smart real estate development in some respects. The study revealed factors and indicators that the municipality, real estate developers, and other stakeholders should focus on in order to achieve smarter development.