The concept of smart sustainable cities—as a favorable response to different challenges faced in urban areas—is rapidly gaining momentum and worldwide attention. This trend has driven the exploration of various technologies to improve the utilization of limited resources and idling capacities (i.e., underutilized physical assets such as buildings or facilities). In fact, a new business model has been introduced recently to smart cities, known as “shared economy”. The shared economy is a socioeconomic system that enables intermediary exchanges of goods and services between people and/or organizations, which boosts productivity and leverages underutilized resources to maximum potential. However, one of the inherent issues hindering the wide adoption of shared economy systems is the lack of trust between the providers and users of such systems. To this end, this study focuses on long-term shared properties/buildings and proposes an intelligent, IoT-enabled device and dynamic pricing model to address the issue of information asymmetry. First, 10 indicators were identified to assess the condition of the shared property. Next, multiple sensors were used, calibrated, and integrated into an IoT-enabled sensing device where the collected data was combined using intelligent sensor fusion technologies in a real-time manner. Third, a survey was developed and distributed to examine the significance of the 10 indicators, and an innovative reliability index was created accordingly to reflect the overall condition of the shared property. Fourth, a dynamic pricing model was developed to reward condition-conscious property users and penalize condition-unconscious ones. To ensure applicability and robustness of the proposed device and model, a pilot project was implemented in a smart long-term rental property in Newark, NJ, United States. Ultimately, this research provided insights on how to improve the operational efficiency of shared economy systems by offering (1) the providers of shared properties visibility over the condition of their properties through real-time assessment of the user reliability, and (2) the users of shared properties assured safety and monetary incentives to maintain the shared environment in a good condition.