Chow Kit Road, a busy shopping sanctuary flourishes with economic activities with more than 500 ‘street children’ roaming and living off the streets. These children have been ignored, and much of their life challenges remain unaddressed. This conceptual paper initiates an educational discussion in relation to their environment with a specific architectural design solution. The intervention infuses concepts formed through in-depth interviews with the street children as well as their caretakers. Unobstructed observations were engaged in ensuring the reliability of the data apart from literature reviews and case studies. Issues of education and place of belonging are postulated through an architectural perspective. This study suggests architectural initiatives in contributing to the social agenda of physical urban renewal.