The Ipswich River watershed has experienced increasing urbanization in recent years. The river, which supplies water to over 300,000 residents (twice the watershed’s population), was considered one of the 10 Most Endangered Rivers in the U.S. in 2003 due to seasonal low-flow and no-flow events. Seasonal outdoor water restrictions have curbed residential demand; however, impervious surfaces and municipal sewer systems direct much of the runoff outside the watershed. Low-impact development (LID) practices, specifically those that infiltrate runoff, have the potential to keep more water in the watershed, and increase baseflows in the river. This study seeks to ascertain the barriers and motivations that exist to LID adoption. A paper survey including Likert-scale questions and a photo preference component was sent to 1,000 homeowners in the watershed. Analysis of responses employed factor analysis and means comparisons to compare responses between concerned homeowners (those who belonged to the local watershed association) and randomly-selected homeowners. Income and educational attainment were significant variables in both aesthetic preferences and willingness to adopt LID practices. Perceived cost of landscape changes and concern about disease-carrying pests also surfaced as barriers to residential adoption. The findings emphasize alternate strategies for land use planners, landscape professionals and environmental organizations to promote behavioral changes in the way residential landscapes are managed, and policies municipalities could adopt to implement more widespread use of LID practices. More widespread understanding and appreciation of the multiple benefits of rain LID landscapes could also serve all three groups.