Background: The increase in aged populations in Malaysia has brought unprecedented challenges to families, policy makers, scholars, and business organisations. This paper adapted the WHO 2007 framework of features of age-friendly cities to examine age-friendly environment constructs and their linkages with social connectedness from the perspective of Malaysian middle-aged and older adults caring for themselves. Methods: A face-to-face cross-sectional survey was conducted on 402 middle-aged and older adults caring for themselves across selected states in west Malaysia, selected via purposive sampling. Firstly, features of age-friendly cities were explored through exploratory factor analysis involving 82 respondents. Subsequently, structural equation modelling was performed, involving 320 respondents. Results: The results indicated that the constructs of an age-friendly environment were built environment, community support and health services, civic participation, and employment as well as communication and information. The structural model provided evidence that implementing age-friendly initiatives relating to built environment, community support and health services, civic participation and employment as well as communication and information enables the ageing population to improve their connectedness with society. These findings supported the ecological theories, agreeing that age-friendly environments help middle-aged and older adults caring for themselves to increase their adaptability and reduce perceived pressure from the environment. This result was in line with the current literature in which an age-friendly environment is a form of support and an enabling environment to cultivate positive social relationships and connectivity. Conclusions: Creating an age-friendly environment that supports active and healthy living for middle-aged and older adults caring for themselves allows them to continue to share their experiences, knowledge, and wisdom. This is helpful and beneficial for societal well-being and economic development as well as for the future generations.