The gazebo was originally erected as part of an early colonial Auckland property owned by the prominent lawyer Edwin Hesketh and his family in the late 1800s. It was built sometime between 1884 and 1899, as a focal point in the landscaped gardens of St John's Wood or Hesketh House. The property covered 2.4 hectares (6 acres), containing a very large two-storey residence of Italianate design. The grounds included a formal landscaped area in front of the house, in which the gazebo was located, and a 0.8 hectare (2 acre) orchard to the rear with vineries and arbours.

Landscaped gardens became increasingly popular during the nineteenth century in Britain and its associated colonies, as a wealthy middle class sought to emulate the grounds of aristocratic houses, albeit on a smaller scale. Garden structures, including gazebos, were common features in such grounds, ornamenting the landscape as well as fulfilling functional roles. Gazebos, or summer houses, provided shelter from the elements and a focus for perambulation, allowing enjoyment of the gardens from somewhere other than the main residence. As decorative elements reflecting passive leisured activity, they also came to be seen as symbols of gentility.

Representative of its kind, the gazebo was designed as a small, free-standing structure, intended to stand out among its surroundings. It opened towards the north, providing a sunny and sheltered place to look out over the extensive lawn surrounded by mature trees. Its architectural style, in part, mirrors that of Hesketh House, although with greater ornamental embellishment and flourish. Access to the house via a gated driveway from Margot (then known as Williamson) Street involved passing through the total length of the lawned grounds, with a full view of the summer house.

By 1899, Hesketh House itself contained eight bedrooms, with servants' quarters, a school room and an organ chamber, as well as reception rooms and service rooms. Several sources mention that it was built for the Hesketh family shortly after they purchased the property in 1874 and named it 'St John's Wood'. However, there is a likelihood that part of the structure was built at an earlier date than this. Prior to Hesketh purchasing the property, the land was part of a 11.6 hectare (29 acre) block originally bought by Charles Moffitt. It was then bought by Thomas Crummer, followed by James Williamson, before Henry Hardington purchased it in 1859 and subdivided it into smaller sections, one of which was sold to Hesketh.

Edwin Hesketh was a prominent barrister in early Auckland. Born in Manchester in 1843, he came to New Zealand with his family in 1859. He began practicing law in 1865 and started his own law firm, Hesketh Richmond & Co., in 1870. The Auckland Weekly News noted in 1886, that '[s]ince Mr. Hesketh commenced practice at the bar he has been engaged in almost all the heavy and important cases that have come before our courts'. Hesketh's firm is still in practice today, under the name Hesketh Henry, and is one of the largest law firms in Auckland.

Hesketh had a long and close association with the Anglican Church, and particularly with St. Mark's Church in Remuera Road. He was the organist and often choirmaster for 30 years, from 1863 to 1893. He was also a generous benefactor of the church as well as being vestryman, synodsman and Chancellor of the Diocese. Hesketh died at St. John's Wood in 1898 and was buried in St Mark's churchyard.

The architectural design of the gazebo not only reflects the style of Hesketh's Italianate residence, but also the Gothic appearance of many Anglican churches in the Auckland region. St Mark's itself employed a more restrained form of Gothic Revival, although its interior was ornate. Then highly ornamental Carpenter Gothic version of Gothic Revival was generally reserved for residential structures, as at Highwic in Newmarket, Auckland.

Several years after Hesketh's death, in 1903, the Diocesan Board purchased the property from his estate for £4,250. The Diocesan High School for Girls was established by Bishop Neligan to provide a religious education for girls in Auckland. As part of the new school complex, the gazebo continued to provide a focus for recreational activities. School photos were taken in front of the gazebo for many years and the lawns around the gazebo were converted into tennis courts for a time. Old girls tell stories of climbing up into the ceiling of the structure and hiding there when they were very small. It is possible that the gazebo was retained for its aesthetic appearance and as a symbol of gentility, appropriate for an Anglican girls' school. The school's influential first headmistress, Mary Pulling (1871-1951), aimed to create an institution that drew from a specifically New Zealand Anglican inheritance, and she was herself particularly interested in architecture and design.

Modifications were made to the gazebo during the twentieth century, including the removal of doors and window glass. Photographs from the 1930s show that there were leadlight lattice panes in the openings of the gazebo. At this time, the larger arched openings held casement windows, while the smaller apertures contained fixed panes. The main entrance had bifold doors, with leadlight lattice glass in the top half. The windows and doors were removed in the 1940s.

Today, the gazebo remains an important feature of the school. It is still located in its original position, although mounted on a concrete footing since the original timber floor rotted in the 1960s. The building was restored in 2002-2003 and remains in very good condition. The structure is believed to be one of very few nineteenth-century gazebos to survive in the Auckland region, and appears to be an unusual remnant of its type in New Zealand. A small number of gazebos have previously been registered by the New Zealand Historic Places Trust, including the Elderslie Gazebo in the Oamaru Public Gardens (NZHPT Register # 7150, Category II historic place) dating to circa 1860, and another at Seatoun, Wellington, (NZHPT Register # 3651, Category II historic place) dating to circa 1903.