In the face of environmental challenges of unprecedented scale and urgency, the European Commission enacted in 2019 a new comprehensive growth strategy with the aim of reaching net zero greenhouse gas emissions in 2050. Named as the European Green Deal, this strategy includes energy, biodiversity, pollution, and climate adaptation targets, and envisages that all EU actions and policies will contribute to its objectives. However, to date, specific actions addressing biodiversity, climate adaptation, and health issues from within the energy sector are still missing or lagging behind. This research proposes a new form of Renewable Energy Community (REC), which combines the use of solar photovoltaic panels with green, namely vegetated, roofs to address multiple Green Deal’s objectives. First, this form of REC was grounded in the current European legislation so to ensure its eligibility for the support schemes that Member States are currently required to devise. Next, the costs and benefits of this REC were determined with value transfer for a case study in Esch-sur-Alzette (Luxembourg) and a probabilistic cost-benefit analysis (CBA) was conducted. By applying Scenario Discovery, the CBA was simulated under different combinations of input parameters and rather than only providing multiple net present values (NPVs), the ranges of input values resulting in desirable NPVs were determined. As a result, the conditions under which the photovoltaic-green roof energy community becomes economically convenient were determined, providing guidance to national policymakers designing RECs’ incentive schemes at present.