Hundreds of cities and communities in the world have joined the WHO’s Global Network for AgeFriendly Cities and Communities since 2010. In order to do quantitative assessments of the age friendliness of cities, the Age-Friendly Cities and Communities Questionnaire (AFCCQ) was developed for the Dutch municipality of The Hague. The purpose of this study was first to translate and test the validity and reliability of the AFCCQ for use in North Macedonia and second to explore perceptions on age-friendliness of the bicultural and bilingual City of Skopje. The AFCCQ proved valid for use in North Macedonia. Overall, older adults in Skopje experience the age-friendliness of the city as neutral (in seven out of nine domains). The best score (“slightly satisfied”) was found in the domain of Housing, which was rated positive in all ten municipalities. The lowest total score (“slightly dissatisfied”) was found in the domain of Outdoor spaces and buildings, which received negative scores in eight out of ten municipalities. In five out of nine domains differences were observed between the Albanian and Macedonian communities. The Albanian sample has slightly higher scores in two domains: 1) Housing and 2) Civic Participation and Employment, while the Macedonian sample scored higher in three domains: 1) Communication and Information; 2) Outdoor Spaces and Buildings and 3) Transportation. A hierarchical cluster analysis further revealed the presence of six distinct age-friendly typologies that can be used for a better understanding of subpopulations in the city and draft policies and action programs on the city level.