William Jones's original foundation provided for a schoolroom, on the site of the present chapel, houses for the Headmaster and Lecturer, and almshouses segregated by sex.
A painting by J.A. Evans, of later date and purchased on behalf of the school by the then Headmaster Lionel James in 1921, shows the buildings and is titled The Old School Room.
Built A.D. 1614.
Pulled down to make room for the present school room, 1865.
Nothing of these buildings remains.
The local writer and artist Fred Hando records that the bell, which hung above the schoolroom, was cast at the Evan Evans foundry at Chepstow in 1716.

In 1864 the Haberdashers undertook a substantial rebuilding of the school.
Funded by the rising fortunes of Jones's bequest on the back of the Victorian expansion of London, the work was mostly undertaken by William Snooke and Henry Stock, of the firm Snooke & Stock, surveyors to the Haberdashers' Company.
Snooke built the chapel, two schoolrooms and a classroom in 1864–1865, followed in the 1870s by the library, Headmaster's House and the buildings which now form Monmouth House and Hereford House.
 These buildings are all Grade II listed.
The Monmouth Alms Houses, on Almshouse Street, were rebuilt by J. B. Bunning in 1842, and redeveloped by William Burn in 1895–1896.
They now form part of the school and  incorporate a large inscription panel describing the benefactions of the Jones Foundation.
The almshouses are also Grade II listed.
The chapel was further extended in 1875.
Snooke's work was not universally praised; a report from the School's Commissioner commenting, "the architect has arranged the buildings in a most inconvenient manner, and the ventilation is deficient."
School House, with its ceremonial arched entrance and coat of arms facing the Wye Bridge, and the adjacent technology block, were designed by Henry Stock in 1894–1895.
They are Grade II listed buildings as of 8 October 2005.
The style of the School House block mirrors that of the main block of Haberdashers' Monmouth School for Girls, which Stock designed at the same time.
The war memorial was dedicated in 1921, Angus Buchanan (VC) attending the ceremony.
The memorial is a Grade II listed structure.
To the west of Stock's School House block, and set into the wall previously facing the Wye, and now completely overshadowed by the A40 by-pass, is a pair of iron gates, of 18th century date and installed at the school in 1941, that come from the Haberdashers' Hall in London which was destroyed during the Blitz.

The school's building of greatest architectural merit is the Grade II* listed Chapel House.
The architectural historian John Newman describes the 18th century building, situated on the Hereford Road away from the main school site, as "the best house in the entire street".
More modern developments include the Hall of 1961, redeveloped in the early 21st century and now the Blake Theatre, the Red Lion Block of the same date and the Science Block of 1981–1984.
In 1985–1986, two ceramic murals were designed for the chapel by the Polish religious artist Adam Kossowski, a friend and wartime colleague of the school's Head of Art from 1947–1978, Otto Maciag.
Executed by Maciag, and another art master at the school, Michael Tovey,  the murals were dedicated at a service conducted by the Bishop of Monmouth, the Rt Rev Clifford Wright on 3 October 1987.
He described them as "masterpieces of twentieth-century religious art”.
In November 2008, a £2.3 million sports pavilion was completed and opened by the former British Lions player and Welsh captain, Eddie Butler, an old boy of the School.
 It was designed by the architects Buttress Fuller Alsop Williams.
In 2011 the school began the Heart Project.
 This led to the sale of some outlying sites, such as St. James's House, and the re-organisation of others, to assist in the raising of funds for the redevelopment of the main school site.
 Further funds came from the Haberdashers' Company, and the first phase was completed with the rebuilding of the Red Lion Block, now renamed the William Jones Building.
William Jones's original foundation provided for a schoolroom, on the site of the present chapel, houses for the Headmaster and Lecturer, and almshouses segregated by sex. A painting by J.A. Evans, of later date and purchased on behalf of the school by the then Headmaster Lionel James in 1921, shows the buildings and is titled The Old School Room. Built A.D. 1614. Pulled down to make room for the present school room, 1865. Nothing of these buildings remains. The local writer and artist Fred Hando records that the bell, which hung above the schoolroom, was cast at the Evan Evans foundry at Chepstow in 1716.
In 1864 the Haberdashers undertook a substantial rebuilding of the school. Funded by the rising fortunes of Jones's bequest on the back of the Victorian expansion of London, the work was mostly undertaken by William Snooke and Henry Stock, of the firm Snooke & Stock, surveyors to the Haberdashers' Company. Snooke built the chapel, two schoolrooms and a classroom in 1864–1865, followed in the 1870s by the library, Headmaster's House and the buildings which now form Monmouth House and Hereford House.  These buildings are all Grade II listed. The Monmouth Alms Houses, on Almshouse Street, were rebuilt by J. B. Bunning in 1842, and redeveloped by William Burn in 1895–1896. They now form part of the school and  incorporate a large inscription panel describing the benefactions of the Jones Foundation. The almshouses are also Grade II listed. The chapel was further extended in 1875. Snooke's work was not universally praised; a report from the School's Commissioner commenting, "the architect has arranged the buildings in a most inconvenient manner, and the ventilation is deficient." School House, with its ceremonial arched entrance and coat of arms facing the Wye Bridge, and the adjacent technology block, were designed by Henry Stock in 1894–1895. They are Grade II listed buildings as of 8 October 2005. The style of the School House block mirrors that of the main block of Haberdashers' Monmouth School for Girls, which Stock designed at the same time. The war memorial was dedicated in 1921, Angus Buchanan (VC) attending the ceremony. The memorial is a Grade II listed structure. To the west of Stock's School House block, and set into the wall previously facing the Wye, and now completely overshadowed by the A40 by-pass, is a pair of iron gates, of 18th century date and installed at the school in 1941, that come from the Haberdashers' Hall in London which was destroyed during the Blitz.
The school's building of greatest architectural merit is the Grade II* listed Chapel House. The architectural historian John Newman describes the 18th century building, situated on the Hereford Road away from the main school site, as "the best house in the entire street". More modern developments include the Hall of 1961, redeveloped in the early 21st century and now the Blake Theatre, the Red Lion Block of the same date and the Science Block of 1981–1984. In 1985–1986, two ceramic murals were designed for the chapel by the Polish religious artist Adam Kossowski, a friend and wartime colleague of the school's Head of Art from 1947–1978, Otto Maciag. Executed by Maciag, and another art master at the school, Michael Tovey,  the murals were dedicated at a service conducted by the Bishop of Monmouth, the Rt Rev Clifford Wright on 3 October 1987. He described them as "masterpieces of twentieth-century religious art”. In November 2008, a £2.3 million sports pavilion was completed and opened by the former British Lions player and Welsh captain, Eddie Butler, an old boy of the School.  It was designed by the architects Buttress Fuller Alsop Williams. In 2011 the school began the Heart Project.  This led to the sale of some outlying sites, such as St. James's House, and the re-organisation of others, to assist in the raising of funds for the redevelopment of the main school site.  Further funds came from the Haberdashers' Company, and the first phase was completed with the rebuilding of the Red Lion Block, now renamed the William Jones Building.
Monmouth School