Windsor Road did not exist until about 1850. The original route to Windsor was over the Thames by ferry or bridge, or from the Slough Road to Eton and over Windsor Bridge. At the foot of the present Queens Road there was no road to Windsor and no houses beyond that point, only a footpath crossing the present golf course.
With the arrival of the railway and the associated Windsor Improvement Plan, Datchet Bridge was removed and the Victoria and Albert bridges were built, with new roads leading across them: Windsor Road and the extension of Southlea Road.
None of the houses in Windsor Road date from before the late Victorian period, apart from the Willows on the Queens Road corner.