Prior to 1922 Calton Avenue was known as Calton Road. The name was changed, at the London County Council’s request, to avoid confusion with another Calton Road in Enfield. The first section of the road, named after the family that sold Dulwich Manor to Edward Alleyn, was built around 1880 and connected the Village end of Court Lane with the newly constructed Woodwarde Road. A dotted line on the 1886 Estate Map shows a projected route north-westwards over the fields towards Townley Road but, until the mid-1890s, there was only a footpath - fenced in 1887 to provide a secure route for pupils walking from the Village to the new Alleyns School. Construction of the Townley Road end of the road began in the mid-1890s specifically to provide better access from East Dulwich to the newly completed St Barnabas Church.

Prior to 1860 Court Lane ran directly into Dulwich Village (or High Street Dulwich as it was then) between the burial ground and the Long Pond, one of several reservoirs in the area. This pond was filled in between 1859-60 using the spoil generated from the construction of the Southern Relief High level sewer which runs through the centre of Dulwich Village and up through the Alleyns School playing fields towards Lordship Lane.

The current block of shops and flats on the corner of Calton Avenue and Dulwich Village dates from1922-23. Built to the design of the Estate Surveyor, C E Barry, it replaced the forge and the blacksmith’s house which had stood on the site from the C18. The blacksmith’s house was formerly known as the ‘White House’; in the 1820s and early 1830s it had been a grocery and milk store run by the parents of local character (and artist) Tom Morris. The lease on the old buildings had run out before WW1 and there had been several proposals to demolish and replace them with a petrol station and garage, but in the end the Estate decided on the current building. It was developed by local builder Mitchells and remained in the family ownership of G A Dean, the managing director, until 1968 when the Estate acquired the lease for £35,000.

The S G Smith garage and workshop site was originally occupied by a row of houses. In the early 1860s, following the filling in of the Long Pond, the Estate had put the area of land behind the forge, then known as Russell’s Field, up for sale to speculative builders to construct small houses. The only bidder had been local builder J W Sawyer and between 1866 and 1868 he built 16 houses and cottages either side of what is now Gilkes Place (then Elms Road).

Charles H Pickup had been running a garage in Elms Road since 1913 and when he wanted to expand after WW2, all the houses on the current garage site were demolished. The petrol station that used to be here was opened in 1967 - it had been used as a builder’s yard until 1960 when S G Smith took over Pickup’s garage and rebuilt the large workshop behind.

The houses on the corner of Gilkes Place and Calton Avenue date from the 1980s - this site was derelict for most of the 1960s and 70s. The four cottages, numbers 11-17 Calton Avenue were built in the early 1870s while, on the opposite side of the road, the Dulwich Cottage Company’s scheme for working class housing was completed a few years later. An article in the magazine ‘Builder’ dated 29/01/1876 noted that ‘there is a probability of a large number of dwellings for the industrial classes being shortly erected on the Dulwich College Estate. Between 1876 and 1879, the company built a terrace of small houses north-east of the Court Lane/Calton Road junction designed by Estate Surveyor Charles Barry Jnr.

The completion of St Barnabas Church in 1894 had, as noted previously, led to the construction of the new road from Townley Road specifically to provide decent access for the congregation from East Dulwich to the new church. In April 1898 builder J H Cooper of Worcester Lodge, East Dulwich Grove, agreed to lease a 170 foot frontage ‘south of the Presbyterian church parsonage garden fronting on the north-western part of the future Calton Road’. He contracted to build two pairs of semi-detached houses to a value of £550 each (Nos 93-99). He had a reasonable track record building on the Estate - his first development had been on the south side of East Dulwich Grove in 1887 (Nos 156-164 remain), moving on to the north side in 1888 (only No 181 remains).
The first four houses had clearly sold well as by February 1899 he was offering to take an additional 180 foot frontage at 5s per foot with a contribution to the standard sewer charge of 8s a foot. He agreed to build three further pairs of semis on 30 foot frontages to cost £650.

In May 1901 he offered to take a much longer frontage and build a further seven pairs of semi-detached houses to cost not less than £675 for a 30 foot frontage and £550 for a 25 foot frontage. The frontages were slightly amended as, in the following month, the Estate’s Surveyor reported that ‘the houses will have a frontage of 26 feet and will contain, on the ground floor, drawing room, dining room, kitchen, scullery and other offices and a conservatory. On the first floor three bedrooms, bathroom and separate WC and, on the second floor, two more bedrooms and a box room. The house will have red brick fronts with the flank and rear walls in stock bricks with tile roofs. They will cost £900 -6s’. There was further discussion about the appearance, particularly of the side elevations. This was resolved by the builder agreeing to the Estate Surveyor, Charles Barry Jnr’s suggested design.

In June architect A E Mullins, of 48 Peckham Road wrote to the Estate with a proposal. Mullins said that his client was prepared to build in the gap but that he thought that the older ‘working class’ dwellings opposite the site would impact on the desirability of his larger style of house, and asked for permission to reduce the size and value of the houses on this last section. The Estate was initially unwilling but, after some discussion, probably involving money, they changed their minds. The following month they agreed to allow three houses valued at £350, and a builder’s yard, so long as the building fronting the yard looked like a house. No 23 remained a builder’s yard for many years and, until relatively recently, had garage style doors at ground level.

The last three houses to be built in Calton Road before the outbreak of WW1 were ‘White Cliff’, the former doctor’s house and surgery on the corner of Woodwarde Road, and No 36. The former dates from 1906 -1908 and was designed by architect W J Almond for local GP Dr Parrott. No 36 dates from 1911-12 and was originally built for a Miss C E Milner and designed by architect Treacher & Sons - Sharon O’Connor’s Journal article in Winter 2009 gives more details. The St Barnabas vicarage was completed in 1915 to the designs of William H Wood, the original architect of St Barnabas.

Nos 30, 32 and 34 date form the 1920s. Ernest Cole, who also designed the St Barnabas Parish Hall in the Village, was the architect, and they were built for the prolific local developer H A Willmott. The last house to be completed was No 28- it stands on a former allotment site and dates from 1961, Austin Vernon & Partners were the architects.