The Cradle to Cradle (C2C) paradigm is emerging as an important regenerative design approach. C2C is aiming to create a positive footprint of the built environment, beyond carbon neutrality. However, there are very few studies that address the application of the C2C concept in building design. More importantly, there is hardly any documentation processes on methods or tools currently being used to design and evaluate C2C buildings. Therefore, the purpose of this paper is to design, model and assess a C2C building prototype with a focus on energy and materials. The research methodology is based on literature review, case study design and performance (energy/materials) evaluation (DesignBuilder/SimaPro). The paper articulates the values, principles and goals of the C2C paradigm and translates them through the prototype design in the Swiss context. The results of the prototype design point to a 74% independence from non-renewable energy resources, compensating the operating and embodied energy during the building’s life. On the other hand only 8% of the building materials were totally recyclable according to the C2C principles. The design process delivers insights on the application of the C2C concept in the built environment reporting on the limitation and means of improvement.