Vitamin D deficiency/insufficiency has been primarily associated with skeletal disorders, however, since vitamin D receptors are found on multiple types of cells, there is also a link to increased chronic disease risk and all-cause mortality. The aim of this study was to examine whether deficient/insufficient vitamin D levels are associated with risk factors of chronic diseases and cognitive dysfunction in 50 to 70 year old adults. Participants completed the health status, three-day dietary record and vitamin D food frequency, sun exposure, and international physical activity questionnaires. Cognitive function of the participants was assessed using the Automated Neuropsychological Assessment Metrics while body composition (percent body fat, android/gynoid ratio) was assessed using Dual Energy X-ray Absorptiometry. Applanation tonometry was used to obtain pressure wave forms at the radial artery to examine arterial stiffness and central pressures. A fasting blood draw was taken to measure vitamin D, blood lipid and glucose levels. Fifty percent of the participants (36/72) were vitamin D deficient/insufficient. Individuals in the low physical activity (PA) group had lower serum vitamin D concentration compared to those in the high PA group (p = 0.04). Moreover, serum vitamin D levels were negatively related to risk factors of chronic diseases; blood glucose (r = −0.38; p = 0.01), triglycerides (r = −0.27; p = 0.02), and android/gynoid ratio (r = −0.32; p = 0.01). Deficient/insufficient vitamin D levels are linked to the risk factors of chronic diseases in men and women aged 50 to 70 years.