Introduction: Loneliness is associated with poorer cognitive functions, lower quality of life, with increased mortality and healthcare utilization. Despite an estimated 2-5% of elderly residing in nursing homes, there is limited knowledge on their loneliness experience. This study seeks to obtain an indicative prevalence of loneliness among nursing home residents in Singapore, explore associations of loneliness with different variables, and better understand their loneliness experience. Methods: A cross-sectional mixed methods study was conducted between May to July 2018. Loneliness was determined by the UCLA three-item loneliness scale, with other information collected on health statuses and social contacts. 57 cognitively-intact nursing home residents above 65 years old were recruited for the quantitative strand, and prevalence ratios were estimated using modified Poisson model with robust estimator. Eight participants were subsequently recruited for the qualitative strand, where analysis was conducted using a lineby-line inductive approach with grounded theory techniques. Results: 59.6% of study participants experienced loneliness. After statistical adjustment, significant associations were detected between frailty and loneliness, and history of falls and loneliness. The estimated prevalence ratio of loneliness among frail elderly is 1.37 times that of those pre-frail (p=0.018), and estimated prevalence ratio of loneliness among elderly with history of falls is 1.35 times that of those without (p <0.0001). The loneliness experience may be amplified by deficiencies in health, social contact, and engagement, and mitigated through reminiscence and anticipation. Individuals' perspective of circumstances and autonomy levels may amplify or mitigate loneliness. Conclusion: This study reinforces existing evidence of relationship between frailty and loneliness, and illustrates a potential association between history of falls and loneliness. With older and frailer elderly residents, and circumstances such as structured routines and lack of autonomy, the observed experience may be unique to nursing homes, with potentially higher loneliness prevalence compared to community-dwelling elderly.