Freeland was founded as a medieval freehold, probably originating around the site of the present Elm Farm, near a wood called the Frith in the 13th century.

The older part of the Village lies around the Green and by the two Churches, with Blenheim Lane and Pigeon House Lane leading off from this area. Several housing developments are found either side of Wroslyn Road (the main road through the Village) which were built in the latter half of the twentieth century. These include: Parklands, Church View, Walkers Close, Broadmarsh Lane, the Blowings, Woodlands, Websters Close, Hurst Lane, Nash Lane, Oakland Close, Busby Close and (most recently) the Dawes on the A4095 Witney Road and Willoughby Fields at the site of the former garage on Wroslyn Road.