Low-density residential development patterns in New England have resulted in the excessive loss of farms, forests and other open spaces and increased automobile dependence. Coupled with increasingly high land costs, sprawl has contributed towards an affordable housing crisis in Massachusetts. The need for sustainable development (such as new urbanism and smart growth) has been increasingly recognized, yet efforts have been hampered, in part, due to apathy and local residents’ resistance towards increasing residential densities, resulting in limited choices for willing homebuyers. This study examines perceptions of residential neighborhoods and sustainable development among residents in Hopkinton and Southborough, Massachusetts; two communities with rural and suburban character located in the rapidly growing metropolitan Boston region. A photo-based survey sent through the mail asked respondents to rate scenes of innovative residential settings and to answer questions about their attitudes towards environmental issues, planning approaches and neighborhood preferences, their current residential setting and demographic characteristics. The results from 253 survey respondents showed three important themes: (1) that residents expressed strong environmental values yet many lacked awareness of the environmental impacts of low density housing, (2) strong preference for views of nature and open spaces was prevalent and (3) visual design variables can dramatically influence perceived density. Key findings indicate two sub-groups. Approximately one-third of the respondents strongly support denser, sustainable development alternatives and value neighborhood planning that reduces auto dependency, meets the needs of households with various incomes and protects open space. While, the other two-thirds of the sample favor calm, scenic, low density neighborhoods and would like to see their community preserve its open spaces and maintain its historic and rural aesthetic. The study concludes with recommendations for regionally appropriate approaches to sustainable development that take into account the multiple scales and stakeholder involvement.