By 1835 Woodman's Inn (in weatherboard) existed on the site of the early road gangs' encampment at Twenty Mile Hollow.

He fell on hard times, heavily mortgaging the property and being sentenced to two years on a road gang for stealing slabs of wood at Springwood.

has been identified on a (now) adjacent block of land that appears to date directly from the Fairfax period of ownership of the property (1860/70), suggests local horticulturist teacher with TAFE, Doug Knowles.

Fairfax renamed his home "Woodford House" and built the second-storey east wing, primarily to accommodate his Sydney friends and their servants.

During his time here he bought more land c. 1868 and then owned 90 acres on which he created an orchard and house garden to provide fresh food for his guests.

[1][2]: 7 Over 300 students were educated in the Blue Mountains location between 1907 and 1925, benefitting from a curriculum based on the liberal arts with commercial subjects available for those intending to enter business life.

[1][3]: 12 Over the duration of World War I, fifty four boys from Woodford Academy enlisted to serve King and country.

Interactive ebooks are progressively developed and displayed at the Academy museum on the centenary of the month each boy enlisted for the Great War.

[12][1] The National Trust received a $1m Centenary of Federation grant from the Australian Government in 2001[9] which O'Keefe had a major part in obtaining, to help restore the property.

New primary and high school programmes have been launched, museum displays have been updated, the dining hall repainted, sandstone re-laid on the front verandah and external timberwork repaired.

[14][1] A lively new volunteer team at Woodford Academy have turned the fortunes of the property around from 2013–2015, also making it a centre for Blue Mountains artistic innovation.

Cutting-edge performances using local talent to interpret the historic complex with sound, light, colour, taste – in new ways not before contemplated.

The "Make your mark in history" project, developed to commemorate students of the Academy who fought in World War I received a 2015 National Trust Heritage Award.

The Norman Lindsay Gallery, Everglades and Woodford Academy were all represented in the Blue Mountains Winter Magic street festival which attracted over 30,000 people.

[1] Of all the site features however, the engraved (with boy students of the Academy's names: there are many such, e.g. RSBS who was Ralph Sanders Barclay Sillar, a student in 1909 and after World War I, a successful lawyer, who lived on until 1970[2]) on the massive rock shelves at the site's rear (east) are probably the most interesting because they graphically demonstrate the use of the building as a school in the early 20th century.

[1][3]: 24 Four Monterey pine trees (Pinus radiata) flank the south-west edge of the property onto the Great Western Highway.

A large mature and significant eucalypt tree grows close to the centre of the main building facing the highway.

Here the curtilage should extend to the railway property on the other side of the road with the view of controlling development directly opposite the site.

[3]: 16 The Woodford Academy shows layers of growth from the original two-roomed inn at the east end of the south block to the present footprint.

The gabled roof is clad in galvanised iron (Moorewood & Rogers) tiles and has a brick chimney at the east end.

A pair of french doors with bead flush lower panel and a toplight open to the east end of the verandah.

[1][18] As of 23 July 2021, the oldest complex of colonial buildings in the Blue Mountains, Woodford Academy has had a distinguished history as a major private school as well as a Victorian country retreat, a significant inn and a seventy-year association with the McManamey family.

The site has considerable historical archaeological value and research potential to demonstrate the general character of its types of occupation from the early nineteenth century onwards.

Previous monitoring of works indicates that significant archaeological deposits survive here which will provide evidence of the specific construction, form, nature, function and occupation of the former buildings and other structures on this site and its environs.

The earliest house in the mountains, Woodford Academy has had a distinguished history as a major private school as well as a Victorian country retreat, a significant inn and a seventy- year association with the McManamey family.

[1] The place is important in demonstrating aesthetic characteristics and/or a high degree of creative or technical achievement in New South Wales.

Anecdotal evidence further suggests that it is regarded as a heritage icon by both the Blue Mountains community and passing traffic, being highly visible from the main road.

[21] Of social significance being a well known Inn along the Western Road for much of its early history and more recently having various other uses including a school, Woodford Academy and a private residence.

The site has considerable historical archaeological value and research potential to demonstrate the general character of its types of occupation from the early nineteenth century onwards.

Previous monitoring of works indicates that significant archaeological deposits survive here which will provide evidence of the specific construction, form, nature, function and occupation of the former buildings and other structures on this site and its environs.