The conventional building design and construction have detrimental impact onto the environment. With the current pace of development of the contemporary society, these issues cannot be fully addressed with the concept of sustainable design and construction, which is based on causing less harm to the environment. Thus, the regenerative concept is gaining relevance, as it is changing the construction paradigm toward the delivery of a human-centric environment, which, when coupled with the circular economy, aims to enable the natural environment to evolve. In order to have a more frequent delivery of regenerative buildings, it is necessary to broaden the knowledge on regenerative design, which is the objective of this paper. The aim is to investigate the design process, strategies, and technologies that are applied during the design and construction of a refurbished residential building, which is intended to be the first regenerative building in Spain, and is currently in the process of certification as per the Living Building Challenge (LBC) standard. Therefore, a literature review was performed, followed by a site visit of the case-study building. The research is organized according to the seven categories (petals) of the Living Building Challenge standard, and all 20 imperatives of the LBC are discussed. Additionally, the aspects of costs and project management are investigated. The findings point out the main design features and challenges toward the realization of regenerative refurbishment, in order to fully adhere to the demands of the LBC, and discusses their potential for a broader application in rural as well as urban settings. The analysis of the case-study design and construction can serve as a valuable insight to deliver future regenerative buildings and accelerate their implementation in the construction industry. This article is based upon the work of COST Action RESTORE CA16114, supported by COST (European Cooperation in Science and Technology).