The EU 2030 climate package calls for raising energy efficiency, increasing usage of RES and decreasing the carbon footprint. There are stringent requirements for new buildings, but the energy efficiency potential in the existing building stock is still not fully explored. The latest trend in urban energy efficiency is the Positive Energy Block (PEB) strategies for new developments. It includes raising building energy efficiency, optimizing energy flow and implementing renewable energy sources (RES). Transforming all existing blocks in a city centre to a PEB would radically change the pattern of energy supply and consumption. European cities have historic centres with great architectural and cultural value. Any urban regeneration strategies must respect and preserve historic values. This paper describes double multi-criteria analysis evaluating urban blocks from both the energy efficiency and cultural heritage perspective with the goal to select the sample block for a “Smart urban regeneration – transition to the Positive Energy Block” case study. Proposed criteria for multi-criteria analysis to evaluate cultural heritage, liveability and energy efficiency potential describes specific qualities of the urban block. The obtained results show that blocks with higher cultural value show less energy efficiency potential and vice versa. It is recommended to apply cultural value and liveability qualities in the Smart urban regeneration process to those blocks with high energy efficiency potential.