Objective: Older adults are at a high risk for loneliness, which impacts their health, well-being, and longevity. While related to social isolation, loneliness is a distinct, internally experienced, distressing feeling. The present qualitative study sought to identify characteristics of loneliness in older adults living independently within a senior housing community, which is typically designed to reduce social isolation. Method: Semi-structured qualitative interviews regarding the experience of loneliness, risk factors, and ways to combat it were conducted with 30 older adults, ages 65–92 years. The interviews were audiotaped, transcribed, and coded using a grounded theory analytic approach based on coding, consensus, co-occurrence, and comparison. Results: Three main themes with multiple subthemes are described: (A) Risk and Protective factors for loneliness: age-associated losses, lack of social skills or abilities, and protective personality traits; (B) Experience of loneliness: Sadness and lack of meaning as well as Lack of motivation; and (C) Coping strategies to prevent or overcome loneliness: acceptance of aging, compassion, seeking companionship, and environment enables socialization. Discussion: Despite living within a communal setting designed to reduce social isolation, many older adults described feeling lonely in stark negative terms, attributing it to aging-associated losses or lack of social skills and abilities. However, interviewees also reported positive personal qualities and actions to prevent or cope with loneliness, several of which mirrored specific components of wisdom. The results support the reported inverse relationship between loneliness and wisdom and suggest a potential role for wisdom-enhancing interventions to reduce and prevent loneliness in older populations.