Homeless patients have high rates of visual impairment and lower rates of glycemic control than housed patients. Although diabetic retinopathy (DR) is the most common cause of new visual impairment and legal blindness in the developed world, little is known about differential risk factors for and rates of DR in homeless versus housed populations. This study aimed to compare the rates of DR between homeless and housed patients with diabetes at the Greater Los Angeles Veterans Affairs Health care System (GLA) and identify clinical and psychosocial predictors of DR rates. We performed secondary database analyses of veterans with diabetes who received care at GLA between October 1, 2013 and September 30, 2015. We described differences in demographic, clinical, and psychosocial characteristics associated with DR in homeless versus housed patients, and created a logistic regression model to identify independent predictors of DR. We found that diabetic veterans who were homeless, as compared with those who were housed, had higher rates of substance use disorders and mental health diagnoses, more primary care and mental health visits, and were more likely to have had diabetic retinopathy eye screening according to guidelines. Multiple logistic regression modeling predicting having DR, revealed that having DR was independently associated with not being homeless (i.e., being housed), older age, having had retinal screening, anemia, higher systolic blood pressure, insulin use, microalbuminuria, and higher HbA1c. Homeless diabetic veterans' lower rates of DR may be due to the GLA VA's tailored and intensive psychological and medical resources for homeless veteran patients.