In March 1898 Chestnuts House, which had been built in the mid-C19th, and 13 acres of its grounds were purchased by Tottenham UDC. With some additional land, it was laid out as Chestnuts Recreation Ground and opened in November 1900 in commemoration of Queen Victoria's Diamond Jubilee. The house was initially used as a public reading room and museum, later becoming a health clinic until it was demolished in the 1980s to make way for a Leisure Centre. At one time there was an ornamental fountain on a mound and various areas of ornamental planting; avenue of plane trees remain on the west, north and south boundaries of Chestnuts Park.
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Chestnuts House was built in c.1850 for Mr Haynes, a timber merchant. At that time St Ann's Road was still a rural lane where City merchants were beginning to build houses. The OS Map of 1894-6 shows the house with a circular carriage drive, some remnant of which remains today, and behind the house were gardens with a fountain. The boundary of the site to the west follows the line of an old footpath, Blackboy Lane. In March 1898 the house and grounds of 13 acres adjacent to Cornwall and St Ann's Roads were purchased for £7,760 by Tottenham Urban District Council following a poll of ratepayers to decide whether the site should be retained for public use. This was overwhelmingly approved by 911 votes and, with some additional land purchased, it was laid out as Chestnuts Recreation Ground, although the area of gardens were built over by 1913. It was intended as a commemoration of Queen Victoria's Diamond Jubilee and opened to the public in November 1900.
At one time the Recreation Ground boasted a fine circular ornamental fountain on a mound, surrounded by planting, and various areas of ornamental planting. Avenues of plane trees remain on the park's western, southern and northern boundaries. Chestnuts House was initially used as a public reading room and museum, and it was the public library until St Ann's Branch Library was built in 1938. After this it became a health clinic but was demolished in the 1980s to make way for a Leisure Centre, now the Chestnuts Community Centre, which risked closure in 1992.
In 2008 various improvements to the park were carried out by Haringey Council in partnership with the New Deal for Communities team and the Friends of Chestnuts Park. The completion of the works was celebrated in May 2008 by a Community Day organised by the Friends. An open playing field now forms the west side of the park with a café and picnic terrace overlooking a new playground to the south. The eastern side of the park has newly refurbished tennis courts, basketball area, and a new Multi-Use Games Area. The Park Pavilion houses the Chestnuts pre-school playgroup and play centre, and the community centre is located in the south-east corner on St Ann’s Road.
In autumn 2008, consultation was carried out to find out how local people would like to see Chestnuts Park improved further, following which a master plan was produced. This provides a long term plan for the park with demolition of the Park Pavilion and the central area of the park completely refurbished. The services that the Pavilion currently runs will be moved elsewhere at some point in the future and if funding allows, the works can then begin in the park. The park gained its first Green Flag Award in 2008, winning this in consecutive years.
Bruce Castle Archives materials; Peter Curtis, In Times Past, Wood Green and Tottenham with West Green and Harringay (Hornsey Historical Society) 3rd ed 1995