The adoption of Precision Farming (PF) practices involving ubiquitous computing advancements and conceptual innovations of “smart” agricultural production toward Agriculture 4.0 is a significant factor for the benefit of sustainable growth. In this context, the dynamic integration of PF facility systems into the Internet of Things (IoT) represents an excessive challenge considering the large amount of heterogeneous raw data acquired in agricultural environments by Wireless Sensor and Actuator Networks (WSANs). This paper focuses on the issue of facilitating the management, process, and exchange of the numerous and diverse data points generated in multiple PF environments by introducing a framework of a cloud-based context-aware middleware solution as part of a responsive, adaptive, and service-oriented IoT integrated system. More particularly, the paper presents in detail a layered hierarchical structure according to which all functional elements of the system cope with context, while the context awareness operation is accomplished into a cloud-based distributed middleware component that is the core of the entire system acting as a Decision Support System (DSS). Furthermore, as proof of concept, the functionality of the proposed system is studied in real conditions where some evaluation results regarding its performance are quoted.