The digital revolution at the end of 20th century has opened some new doors for local communities to take active parts in the new economy. The growing number of home-based teleworkers, e-entrepreneurs and high-rank information workers and firms who are very selective on their live/work locations heralds a new era with a great emphasis on the productive side of residential communities. In this regard, very little knowledge has been produced on the planning regulations that actually facilitate this new role of residential communities and support community-based information work. This paper benefits from empirical data collected from two case studies in the US and Australia where residential communities attempt to attract communitybased information work. It investigates how these two case studies under different regulatory environments respond to the new life/work style of information workers. The result of this investigation opens discussions about the efficient regulatory environment that actually persuades community-based information work. It notes that the new social group of community-based information workers asks for a set of planning regulations that acknowledge their work right, integrates their live/work experience, and creates a mixed-use support system for their different life/work style. This conclusion once again emphasizes the significant share of regulatory environments to adjust the residential communities for their new role in the digital age, and sheds light on the long way ahead to embrace the transformation.