This research is part of a wider study on the sustainability of high-rise buildings within the urban environment. The focus here is on wind and temperature stratifications per different height through in situ monitoring on a high-rise residential tower in the Mediterranean climate of Tel Aviv, and their impact on thermal comfort and user safety. The appropriateness of design is discussed in relation to the direct exposure to higher-up wind velocities, the thermal perception of the residents through questionnaires, and the safety and usability of the outdoors space according to height. The potential for advancing the energy efficiency of the structure is also discussed. The study covers a hot and a cold season, focusing on the specificities of the wind regime in the specific climate, through seasonal variations. Results from the monitoring of data confirmed increased wind and gust velocities per building height all year round, reaching the level of danger for the occupants during winter, cancelling, thus a successful operation of the outdoor balcony space. The occupants’ perception and use of the outdoor balcony space per building height were in direct relationship to the increased wind velocities per height. Discussion and conclusions critically evaluate the residential high-rise building typology in the Mediterranean climate through the design of the outdoor balcony space along the height of the envelope. The results set an initial understanding and delineation for future studies, while underlining the complications of designing and occupying tall buildings and the level of detailing required.