In 2006, the World Health Organization initiated an international movement to enhance active aging and the age-friendliness of communities by focusing efforts on the built, social, and service environment. The global model requires soliciting older adults’ preferences regarding community features although findings are typically aggregated across all aged respondents despite mounting distinctions between the generations. This study aimed to examine the differential salience of community features by older generational age groups including Baby Boomers (n = 639) and Silent and Government or General Issued (GI) Generation (n = 488) in an age-friendly community in which more than half of its residents are age 50 or older. Chi-square results indicate significant differences across the generational age groups in all domains with the greatest distinctions pertaining to preferences in housing, outdoor spaces, employment, and participation in varied social activities. The perceptions expressed by Boomer-aged adults portend implications ahead for multiple sectors and features of community life.