Introduction: Cold hypersensitivity (Hie) is a common complaint among older adults in East Asia and has traditionally been attributed to peripheral circulatory dysfunction. However, emerging evidence suggests that central sensitization (CS) may also contribute. This study examined the association between central sensitization symptoms and the severity of cold hypersensitivity in community-dwelling older adults. Methods: We analyzed cross-sectional data from 586 adults aged 65–84 years participating in the 2024 Otassha Study in Tokyo, Japan. Cold hypersensitivity was assessed using a validated 10-item questionnaire and categorized into four levels (negative, mild, moderate, severe). Central sensitization symptoms were measured using the Japanese version of the Central Sensitization Inventory (CSI). The primary analysis consisted of multinomial logistic regression examining the association between CSI total score (per 10-point increase) and cold hypersensitivity severity, adjusting for age, sex, smoking status, alcohol consumption, and physical activity. Exploratory analyses examined associations between individual CSI items and cold hypersensitivity with false discovery rate correction. Results: Among the 586 participants, 396 (67.6%) were classified as having cold hypersensitivity. In adjusted multinomial logistic regression analyses, higher CSI total scores were significantly associated with increasing severity of cold hypersensitivity. Each 10-point increase in CSI score was associated with higher odds of mild (AOR 1.70, 95% CI 1.35–2.15), moderate (AOR 2.35, 95% CI 1.78–3.09), and severe cold hypersensitivity (AOR 4.33, 95% CI 2.29–8.19), compared with participants without cold hypersensitivity, indicating a graded association. In exploratory analyses, low energy, jaw pain, and headaches remained significantly associated after correction for multiple comparisons. Conclusion: In this cross-sectional study of older adults, greater central sensitization symptom burden was associated with increasing severity of cold hypersensitivity. These findings suggest that cold hypersensitivity may reflect neurophysiological processes related to central sensitization. Longitudinal studies are needed to clarify temporal relationships.