In the West, real estate development has a relatively firm tradition and a clear set of guidelines. Most developers work for the sake of achieving profit and do so according to the framework provided by their respective societies. What happens when individuals and institutions step outside of those conventions, or even laws? Is there room for new paradigms in real estate development? Is there a need? Or are people trying to fix a system that is not broken? Through evaluating instances of counter-culture, unconventional and radical acts in real estate development, focusing on social response and project sustainability, the author seeks to define the significance of these non-standard practices. Information is acquired mainly through media, public record and personal interviews, but quantitative analysis is employed when practical and purposeful. It is possible that some varieties of unconventional acts of development can become minorities of the mainstream, while others will probably remain anomalistic. Generally, results imply that real estate institutions of various sizes can employ more creative development projects and techniques to excel, even in times of economic lull. Additionally, the social aspects of development and resident-engagement are highlighted as a strong component of future sustainability: an individual civilian can have just as much stake in a project as developers, governments and special-interest groups. This paper adds to the discussion of alternative methods in land use and property development and showcases areas for more involved project-related research.