In recent decades, the steady increase of energy consumption from building construction and operations cause atmospheric pollution and significant financial burden, mainly due to the high costs imposed from energy production. This study examines ways under which modern designs of a building can be applied on construction and domestication while following conventional methods of construction, compared to a building that has been constructed and domesticated under bioclimatic architecture. Particularly, two buildings were investigated in terms of the energy consumption incurred, being built on the same seaside area and period of construction and at adjacent plots of the same distance from sea for ease of comparison. The first building (A1) was constructed under the principles of bioclimatic architecture, being also facilitated with green and smart technologies. The second building (A2) was constructed under conventional construction techniques. The energy efficiency of both buildings was calculated by the “TEE KENAK” software, while specific parameters were recorded. Energy classifications of both buildings were valued and a proposed scenario and interventions unveiled the energy classification upgrading from A2 to A1. Our analysis revealed, as also found in the literature, that during thermal energy oscillating conditions, corresponding relative humidity stresses were observed, indicating that the vapor pressure handling should be taken into account towards comfort. The preliminary incremental cost evaluation and comparison of A1 and A2 energy upgrading under the criterion of simple payback period were critically discussed.