The rapid and uncontrolled territorial transformation processes that have characterized the global scenario over the past decades have generated a widespread sense of uncertainty and unpredictability, making the implementation of adaptive and flexible territorial management policies increasingly necessary. The need for urban strategies capable of addressing recent environmental, health, and geopolitical emergencies has consequently grown, through governance plans aimed at the efficient management and mitigation of associated risks. In this context, the real estate sector plays a crucial role in the development of resilient and sustainable urban planning programs. In this regard, the development of planning tools based on an accurate assessment of risks and influencing factors has become highly relevant. Specifically, given the complexity of real estate investments, which involve high initial capital and multiple types of risk, rigorous quantitative and objective evaluation models should be adopted and applied. To this end, this study, through a systematic review of the existing academic literature, identifies and analyses the variables considered most decisive for real estate investments. This research, indeed, aims to support the development of integrated approaches for a comprehensive assessment of the financial, socioeconomic, and market factors that contribute to defining the volatility and uncertainty associated with real estate investments.