The importance of assessing executive functions (EF) using ecologically valid assessments has been discussed extensively. Due to the difficulty of carrying out such assessments in real-world settings on a regular basis, virtual reality has been proposed as a technique to provide complex functional tasks under a variety of differing conditions while measuring various aspects of performance and controlling for stimuli. The main goal of this study was to examine the discriminant, construct-convergent and ecological validity of the Adapted Four-Item Shopping Task, an assessment of the Instrumental Activity of Daily Living (IADL) of shopping. Nineteen people with stroke, aged 50–85 years, and 20 age- and gender-matched healthy participants performed the shopping task in both the SeeMe Virtual Interactive Shopping environment and a real shopping environment (the hospital cafeteria) in a counterbalanced order. The shopping task outcomes were compared to clinical measures of EF. The findings provided good initial support for the validity of the Adapted Four-Item Shopping Task as an IADL assessment that requires the use of EF for people with stroke. Further studies should examine this task with a larger sample of people with stroke as well as with other populations who have deficits in EF.