This work describes the design, development and evaluation of a software Prototype, named ArchReco, an educational tool that employs two types of Context-aware Recommendations of Design Patterns, to support users (CS students or professionals) who want to improve their design skills when it comes to training for High Level Software models. The tool's underlying algorithms take advantage of Semantic Web technologies, and the usage of Content based analysis for the computation of non-personalized recommendations for Design Patterns. The recommendations' objective is to support users in functions such as finding the most suitable Design Pattern to use according to the working context, learn the meaning, objectives and usages of each Design Pattern. The current work presents the Semantic Modeling of the Software Design process through the definition of the context that defines the Software Design process and in particular the representation of the Design Patterns as Ontology model, the implemented Context Aware Recommendation Algorithms and the evaluation results extracted from a user based testing for the ArchReco prototype.