The current study aimed to enhance the sustainable utilization framework of the underutilized Greek native Rosa canina L. (rosehip) germplasm as a potential novel crop that can deliver high-quality products with minimum environmental impact. The first part of the work includes asexual propagation trials on cuttings of two Greek R. canina genotypes, assessing the potential of various alternative rooting enhancers to the conventionally used indole-3-butyric acid (IBA), as affected by rooting substrate and cutting type. The propagation results showed commercially acceptable (>50%) rooting rates for 2500 ppm IBA, coconut water, rooting gel and aloe vera treatments and similar rooting attributes of root number and length, providing evidence for the feasibility of using alternative rooting enhancers. The second part of the work presents the results of an ongoing ex situ cultivation trial assessing the potential of a diversified organic fertilization regime against conventional fertilization on fruit size and yield, coupled with macro- and micro-nutrient concentration, in the leaves of four Greek R. canina genotypes. The results showed a genotype-specific response in rosehip fruit size and yield to fertilization, with the organic regime showing comparable results to the conventional fertilization. In addition, diverse patterns, depending on the element, of macro- and micro-nutrient content were measured in the leaves in both fertilization regimes, which were, however, genotype-dependent. Overall, the current study reports for the first time the potential of alternative rooting enhancers for commercial R. canina propagation coupled with the application of organic fertilization as a means of establishing a diversified cultivation protocol for underutilized R. canina germplasm. The current results can be employed to further facilitate a value chain creation for Greek rosehips as a raw material for use in the agro-alimentary and medicinal–cosmetic sectors.