An ecological approach to land-use planning is essential to maintain the long-term sustainability of ecosystem benefits, services, and resources. Concern about environmental quality and the long-term livability of urban areas is now a driving force in urban planning and design. The interrelated issues of growth management, smart growth, sustainable development, and new urbanism are topics in the most vibrant discussions at all levels of planning and landscape architecture. Within this context, this study starts from the interest in the ecological planning and management in urban areas, especially related to the issue of local development regulation and guidelines. Landscape regulations have come into existence recently in communities across the nation and these regulations vary from one region to another and from one community to another. The aims of this study were to investigate the relationship between ecological landscape structure and local development regulations over time. Comparison analysis was conducted between two areas that had similar pre-development ecological conditions but were developed under vastly different regulatory environments. The Woodlands (regulated to protect ecological condition) and the North Houston area (which followed traditional subdivision regulations) were examined at three different developmental time periods: predevelopment, early development (after 10 years), and matured development (after 30 years). Aerial photos of each site from the three time periods were classified into forested and non-forested classes and the landscape structure was quantified with a number of landscape metrics related to fragmentation??an indicator of habitat degradation. Two factors, the ecological approach to landscape planning and the adoption of more restrictive landscape regulations and guidelines, are discussed on the premise that they exert influence in developing and maintaining the long-term sustainability of ecosystems. In conclusion, this study provides the quantified landscape configuration and composition of the effects of development regulations on landscape structure. The ecologically planned community shows a less fragmented forest pattern and more restrictive development guidelines result in more ecologically structured environments. Understanding how elements of local development regulations affect ecological landscape patterns is important for landscape architects, planners, and administrators because it can lead to better strategies for planning and designing sustainable communities.