Background: The relationship between overweight or obesity and depressive symptoms in individuals with or without cardio-metabolic abnormalities is unclear. In a cross-sectional study we examined the odds of experiencing depressive symptoms in overweight or obese older adults with or without metabolic abnormalities. Methods: The participants included 3318 older adults from the Hunter Community Study Cohort with a Body Mass Index (BMI) ≥ 18.5 kgm2, stratified by BMI and metabolic health risk. Obesity was defined as BMI ≥ 30 kgm2 and metabolically healthy as the absence of metabolic risk factors, according to International Diabetic Federation criteria for metabolic syndromes. Moderate to severe depressive symptoms were defined as a Centre for Epidemiological Studies Depression Scale (CES-D) score ≥ 16. Results: Compared to the metabolically healthy normal weight (MHNW) group, the odds of experiencing moderate/severe depressive symptoms were higher in those classified as a metabolically unhealthy normal weight (MUNW) (odds ratio (OR) = 1.25, 95% Confidence Interval (CI): 0.76–2.06) or metabolically unhealthy obesity (MUO) (OR = 1.48, 95% CI: 1.00–2.19), but not in those classified as metabolically unhealthy overweight (MUOW) (OR = 0.96, 95% CI: 0.63–1.45), metabolically healthy overweight (MHOW) (OR = 0.80, 95% CI: 0.51–1.26), and metabolically healthy obesity (MHO) (OR = 1.03, 95% CI: 0.65–1.64). Compared with MHNW males, the odds of moderate/severe depressive symptoms were increased in all other BMI category–metabolic health groups for males and females. Limitations: Our relatively small sample size and cross-sectional design did not allow us to robustly establish causality. Conclusion: The odds of experiencing moderate/severe depressive symptoms were increased in metabolically unhealthy older adults regardless of normal weight or obesity, with the odds of having moderate/severe depressive symptoms being higher in females than in males.