This paper reports part of a study funded by New Zealand’s National Science Challenge 11: Building Better Homes, Towns and Cities. Unlike the UK and other European settings, in New Zealand there has been very little policy emphasis placed on the development of peripheral regions. Uneven economic development has been a fact of life with very significant growth in Auckland, the country’s largest city, and far less growth in other localities. In the face of this, public, private and third-sector agencies in regional settlements have initiated a range of urban regeneration activities. Our study, focusing on three South Island settlements, Oamaru – Timaru – Ashburton (with a population range of 14,000 to 29,000), has attempted to understand the situation they face and the nature of the initiatives they are pursuing. One set of these initiatives is very much property-related with local government and the private sector both engaging. These include retail facilities, business parks, heritage precincts and service facilities such as hospitality, recreation and accommodation for locals and tourists. At times local government and private sector developers work in harmony, but in others there are elements of antagonism and frustration evident. We use our understanding gained from interviews with local government, property professionals and the development sector to outline to identify a number of cases studies. Each of these emphasising the important roles played by locally based developers in regional settlements and the need to find ways of harnessing their energy and commitment more effectively.