In the 13th century much of the Parish of Tottenham, including the St Ann’s area, was occupied by farmland following the deforestation of areas of the Middlesex Forest. Most of the area was by then covered by open farmland, owned by a few large estates.

Between 1229 and 1264 the Hospital of St Lawrence at Clayhanger was recorded to have occupied a site on Hangers Lane.

The centuries rolled on and by the end of the 18th century, most of the woodland within the parish had been cleared and replaced by pasture and arable farmland. Hanger’s Green had been laid out as a small open space linking Hangers Lane to Black Boy Lane - this now forms part of the forecourt of Chestnuts Primary and Junior School.

Also around 1800, a cluster of houses were also developed in the area. Rose Cottage, was on the north side of Hangers Lane and was to become known as Hanger Lane Farm by 1894.

St John’s Lodge was built on the southern side of Hanger’s Lane within the site of the current St Ann’s Hospital. Charlotte Riddell (1832 - 1906) was a one of the most popular and influential writers of the Victorian period and lived in St John’s Lodge. She used to describe herself as living on "Green Lanes, near Harringay House".

She wrote in 1874:

Sixteen years ago... As for Hanger Lane, no one had yet dreamed of the evil days to come, when mushroom villas should be built upon the ground that not long before was regarded as an irreclaimable morass—when at first a tavern and then a church (the two invariable pioneers of that which, for some unknown reason, we call civilisation) appeared on the scene, and brought London following at their heels . . . when, in a word, Hanger Lane should be improved off the face of the earth and in the interest of speculative builders . . called, as it is at present, St. Ann’s Road, it has only taken sixteen years to change West Green from an extremely pretty village to an eminently unde­sirable suburb.

Several other lodges and villas were constructed in the surrounding area during this period, including Oak Lodge, York Lodge and Oak Villas on the north east side of Hangers Lane and Suffolk Lodge on the south east side. Hanger Green House had been built on the south west side of Hangers Lane set within pleasure gardens laid out with a large ornamental lake utilising the earlier clay workings.

Chestnuts House occupied a site on the north west side of Hangers lane within a large ornamental garden that was later to be incorporated into the eastern part of Chestnuts Recreation Ground.

The population of Wood Green grew steadily during the first half of the 19th century as merchants and traders from the City began to live in the area - by 1841 Wood Green was inhabited by approximately 400 people. The introduction of the railways to Haringey had a considerable impact on the development of the area during the mid to late 19th century.

St Ann’s School for Boys (now demolished), the Hermitage School for Girls (now St Ann’s Junior School and St Ann’s Church (consecrated 1861) were established.

Hangar Lane was rechristened St Ann’s Road in 1872.

St Mary’s Priory was built on the south side opposite the junction with Avenue Road. A row of 13 cottages was constructed on the west side of Suffolk Road for those employed in Lee’s Clay Workings.

A large fever hospital (later St Ann’s Hospital) was established on the open land immediately to the south of St Ann’s Road in 1892.

St Ann’s Road railway station was opened by the Tottenham & Hampstead Junction Railway on 2 October 1882. It was at the corner of St Ann’s Road and Seven Sisters Road. It was never well used and was closed on 9 August 1942 as a wartime austerity measure and never reopened. The station building survived as a newsagents until October 2012, when the building was demolished.

By the beginning of the 20th century most of the residential streets within the area now covered by the St Ann’s Conservation Area were in place. The Chestnuts Recreation Ground (now Chestnuts Park) was formed from the gardens of Chestnut House, which became a public library.

The adjoining land north and west to Black Boy Lane and the rear gardens of the houses on the south side of Falmer Road and tennis courts and a bowling green were established in the north east corner.

A new school (formerly the Woodlands Park Primary School and now called Chestnuts Primary and Junior School) was constructed to the west of the (now Chestnuts Park).

The large Oceana Laundry was established between Cornwall Road and North Grove on St Ann’s Road. In the early years of the new millennium, a new block of flats - Turner Court - was built on the former Oceana Laundry site.