Lyttelton was the place designated by the Canterbury Association as the port, and initially the chief town, of the carefully planned settlement of Canterbury. Although Christchurch later became the principal city, Lyttelton grew to a much more sizeable settlement during the 1850s after the arrival of the first immigrants. The maintenance of law and order was an issue from the beginning, and make-shift lock-up facilities were soon replaced by more permanent premises. The gaol that developed in Lyttelton was to become the principal penal facility in Canterbury until 1915, when the Paparua Prison took over this role. The site on which the gaol was located is central in the town and was originally designated as a market place, though never actually used as such. A plan drawn by Gaoler, James Reston, as part of his 1865 report to the Provincial Government, shows the layout of the gaol. In this year the average number of prisoners was 78, with a staff of one gaoler, one chief warder, eight warders, a matron and an overseer of works. Houses on the Oxford Street frontage of the gaol site were provided for the gaoler and the Chief Warder. In 1870 Town Section 173, which neighboured the gaol's northern boundary, was purchased by the Provincial Government to allow for building extensions. Alterations and additions were considered necessary in order to organize a separation of prisoners within the confines of the gaol, as it was recognized that association with hardened criminals could have a detrimental impact on minor offenders. Major revisions were planned by Benjamin Mountfort and begun under his supervision in 1872. At that time, he was the Provincial Government's Architect, designing all the principal public buildings and making skilled use of concrete for the major institutions like the gaols here and at Addington, and the Sunnyside Lunatic Asylum. The date of construction is not known for the two houses shown on the 1865 plan of the Lyttelton Gaol, but it was considered that they needed replacement as part of the major upgrading of 1872. The new Gaoler's house, set on concrete foundations, was framed in timber, lined internally with concrete and clad externally with corrugated iron. It was well underway when described in the Lyttelton Times, 6th February, 1873. However by the end of 1874, Reston, the Gaoler, was concerned at slow progress with the rest of the building programme and Mountfort was asked by the Provincial Government to explain increasing costs and delays. In the report he wrote in February, 1875 he explained progress, the extra work required to create a stable dividing wall between the gaol site and the new school being constructed ( to his designs) on the southern boundary, and the constraints imposed by the need to retain decaying buildings in use until new ones were completed. He stated: "We have moved across the yard the kitchen and dining shed, while to accommodate the Chief Warder's house the Government have rented a piece of land on the west side of Oxford Street, (the corner of Oxford and Winchester Street), to which the warders house has been moved during the erection of the new cells now in progress. All this necessarily makes the work more expensive". The area of land leased by the Provincial Government was part of the ¼ acre section, TS 62, first owned by William Guise Brittan, (a notable early settler) then sold in 1860 to Jane Wormald (widow of an attorney for the Canterbury Association, never resident in New Zealand). It was divided into three parts, each with a small leased building. One part of the section was leased by a blacksmith from early in the 1850s until the 1870s. In November 1874, the Provincial Government arranged to lease the corner section, an area of 10.3 perches with a frontage of 42 feet to Oxford Street and a depth of 66 feet (12.8m x 20.1m) along Winchester Street. . In December 1883 this section was purchased by the Crown. It was ideally situated for use by gaol staff and for a brief period the head warder must have lived in his relocated house while his new residence was being constructed. Work at the gaol was described in an article in The Press, 24th August, 1875 and it explains the siting of the Chief Warder's house at the southern end of Oxford Street where it was in Reston's 1865 plan. "The building is of concrete, with stone dressings and will be a handsome edifice when completed." Historic photos of the gaol frontage confirm the description and location. . There has been debate as to whether the existing house at 39 Oxford Street is the building shown in Reston's 1865 plan and moved across the road in 1874. There is no photo of the gaol site showing the house to give an indication of its appearance. However, the dimensions for the first chief warder's house as shown on the plan are 30 by 14 feet (9.1m x 4.27m), much smaller than the present house which exhibits no evidence of enlargement. The area of the two storeyed section is 30 feet 6 inches by 16 feet (9.2m x 4.9m), so without the two rooms under the lean-to roof it is of similar size. However, details of finishing throughout the building are consistent with them being completed at one time and there is no sign in the internal framing that the rear two rooms were added later. It seems most probable that this house was constructed once the new Chief Warder's residence was completed on the gaol site and James Arnold, the current Chief Warder, had vacated the small building placed on the site temporarily. There is no reference in surviving records to indicate who designed the existing residence and though Mountfort was responsible for the new complex of buildings around the gaol itself, stylistic evidence does not indicate him as the designer. A pattern book design may have been utilized with prison labour undertaking the unskilled work supervised by Horation Henwood, the Gaol's Clerk of Works. There is also no record in the gaol archives of who resided at 39 Oxford Street and there has been confusion over this issue, especially since a plaque was installed naming it the "Gaoler's House". More recently it has been suggested instead, that it was the Chief Warder's house. Clearly , the officer holding this title would have lived in the specifically built residence within the main gaol confines through the latter part of the 19th century. However, once street directories became more detailed in the early 20th century there are listings in Wise's New Zealand Directory that show the Chief Warder was living here from 1908, and this accords with the memories of older Lyttelton residents. In the final years of winding down, with the decision to close in 1915 and the gaol becoming empty in 1921, there would have been many changes in the use of the 1874-6 buildings and we are left to conjecture about the use of what had been designed as the Chief Warder's concrete residence. We can assume that the timber house at 39 Oxford Street was home to a warder of some seniority from the time of its construction. . By 1877, 13 officers controlled 105 inmates and a year later the number of warders had increased to 19. Accommodation could not be provided for all of these warders, though attempts were made to keep as many as possible on the premises or within close proximity of the gaol. For a brief period after the last prisoners had been moved to Paparoa a section of the gaol was used as a police gaol. After unsuccessful attempts were made to sell the complex, agreement was reached with the Lyttelton Harbour Board for the purchase of all the demolished concrete from the site for use in harbour works. Ownership of the site was transferred to the Canterbury Education Board and the Lyttelton School was able to extend its playground once prison labour from Paparua had completed the demolition. For a time the Gaoler's house was retained as residence for the school caretaker. Across the road the house at 39 Oxford Street remained in Crown ownership but now under the responsibility of New Zealand Railways. In Wise's Street Directory for 1923 the house's occupant is shown as Edward J.Vine, Loco driver. In 1962 the house went back into private ownership when it was sold to Martha Harkess, a widow. It was transferred to R.J. Hanson, seaman, in 1967, transferred again to Mavis E Boyd, housewife, in 1969 and in 1975 to J.S. Downie, watersider. Mr Downie sold the house early in 1997 and the new owner applied for Resource Consent to enlarge the house, almost doubling its existing size and adding a garage from the Winchester street frontage. The publicly notified application was greatly opposed by local residents for whom the house was regarded as one of the town's most important buildings and the application was turned down. At the end of that year the present owners purchased it and have carefully maintained its original form and character.

The two storeyed house faces Oxford Street and the gaol site across the road. On the ground floor are the four principal rooms in a square plan divided by the central passage from which the stair rises. The two front rooms, sitting room and bedroom, are mirrored on the upper floor by two further bedrooms, while the two rear rooms, kitchen and bedroom, are under the steeply sloping lean-to. The lean-to is extended on the northern Winchester Street side to accommodate the original pantry and scullery. Today the kitchen is located in what was the scullery and a bathroom is in the former pantry. To level the sloping site, a stone walled basement was built beneath the room at the south-west corner of the house. The basement is accessed from the exterior. Across the yard from the rear of the house is the former wash-house, complete with copper and tubs, with a flush toilet opening from it. The house's form is tall and narrow with just the four rooms in the two storeyed section. The dominating form of the gables with their decorative barge boards is repeated around the upper section while the frontage is enlivened by the verandah. The decorative timber work has been well maintained, remaining intact. The scalloped detailing of the barge boards terminates with a diamond shaped motif which is repeated across the verandah. The southern gable is undecorated and there were no windows on this side of the building, presumably because it faced the worst of the weather. The present owners have been able to find a sash window of matching form and dimensions and have inserted this in the upper bedroom to allow a view over the harbour. This now completes the symmetry of the two storeyed section. The central front door opens into a generous hallway with a timber archway separating the front section from the rear and screening the foot of the stairway. On the right is the parlour with its original timber framed fire place, backing on to the kitchen stove in the room beyond. A tall brick chimney serves these two fires and one in the upstairs bedroom. It makes a strong accent on the roof line with its three elongated, fluted chimney pots. Throughout the house the skirtings, window and door surrounds are well detailed and original. Walls were lined with scrim and wallpaper, later covered with wall board which has recently been removed. Volcanic stone which was used for the many retaining walls built by prison labour around Lyttelton, forms the wall along the sloping Winchester Street boundary while concrete was used for the base of the decorative iron fence across the Oxford Street frontage and the imposing pillars which frame the gate way. A more durable stone was used for the many gutters laid around Lyttelton by prisoners and there is a well preserved section of this distinctive guttering along Oxford Street in front of the Warder's house.