Since the early 1970s, Ian McHarg's design-with-nature concept has been inspiring landscape architects, community and regional planners, and liked-minded professionals to create designs that take advantage of ecosystem services and promote environmental and public health. This study bridges the gap in the literature that has resulted from a lack of empirical examinations on the multiple performance benefits derived through design-with-nature and the under-investigated social aspect emanated from McHarg's Ecological Determinism design approach. The Woodlands, TX, USA, an ecologically designed community development under McHarg's approach, is compared with two adjacent communities that follow the conventional design approach. Using national environmental databases and multiple-year residents' survey information, this study assesses three landscape performance metrics of McHarg's approach: stormwater runoff, urban heat island effect, and social acceptance. Geographic Information Systems (GIS) was used to assess the development extent and land surface temperature distribution. Results show that McHarg's approach demonstrates benefits in reducing runoff and urban heat island effect, whereas it confronts challenges with the general acceptance of manicured landscapes and thus results in a low safety perception level when residents interact with naturally designed landscapes. The authors argue that design-with-nature warrants multifunctionality because of its intrinsic interdisciplinary approach. Moreover, education and dissemination of successful examples can achieve a greater level of awareness among the public and further promote multifunctional design for landscape sustainability.