This study investigated the association between dietary quality based on the Korean Healthy Eating Index (KHEI), and the prevalence of chronic conditions among middle-aged individuals (40-60 ys of age) living alone. The participants were selected (1,517 men and 2,596 women) from the Korea National Health and Nutrition Examination Survey (KNHANES) 2016-2018 and classified into single-person households (SPH) and multi-person households (MPH). Nutrient intake, KHEI, and the prevalence of chronic conditions were compared according to household size. The odds ratios (ORs) of chronic conditions were analyzed according to the tertile levels of KHEI by gender within each household size category. Men in SPH had a significantly lower total KHEI score (P < 0.0001) and a lower prevalence of obesity (OR, 0.576) than those in MPH. For men, the adjusted ORs for obesity, hypertension, and hypertriglyceridemia in the first tertile (T1) of KHEI scores within SPH compared with the third tertile (T3) were 4.625, 3.790, and 4.333, respectively. Moreover, the adjusted OR for hypertriglyceridemia in the T1 group compared to the T3 group within the MPH was 1.556. For women, the adjusted ORs for obesity and hypertriglyceridemia in T1 compared to T3 within the SPH were 3.223 and 7.134, respectively, and 1.573 and 1.373 for obesity and hypertension, respectively, within MPH. A healthy eating index was associated with a reduced risk of chronic conditions in middle-aged adults. Greater adherence to a healthy eating index could lower the risk of chronic conditions in middle-aged adults living alone.