Forty hectares of land at what was to become Hillsborough was purchased and stocked in 1851 by 'Honest' John Cordy (1805-1886) for Henry Selfe Selfe (1810-70), the Canterbury Association agent in London. Before 1857 Cordy built a single-storey six-room house on the property for £100. Selfe never lived there; he visited New Zealand only once - in company with Lord Lyttelton in 1868. Between 1851 and 1854 Cordy possessed a small run near the Bridle Path; later he managed Homebush for the Deans family before taking up Hororata Station.

In 1863 the Selfe property was sold to Major Henry A. Scott, who named it Glenmore. Scott, who held a commission in the 12th Lancers, arrived in Canterbury with his family in 1854. The founder of the Canterbury Volunteers in 1860, Scott was also a sheep farmer, a member of the Provincial Council, a church property trustee for Lower Heathcote, and a member of the United Cricket Club.

Scott sold to John Barton Arundel Acland in 1865, and returned to England. A prominent runholder, Acland had established Mt Peel station in South Canterbury in 1856. As a public - spirited man however, he had many interests that brought him frequently to Christchurch. Glenmore thus became Acland's town residence. Acland retained Glenmore for 14 years, during which time he apparently added the two-storey section to Selfe's original house.

In 1880 Acland sold Glenmore to John Chapman, who passed it the following year to Robert Allen. Allen had been a Scargill farmer, and owned a sawmill at Little River. Allen stayed until 1893, when he sold the property to his brother-in-law James Haswell Wood. Australian born, Wood arrived in New Zealand with his parents in 1863. Although a saddler by trade, he was manager at Allen's sawmill for a time, and later managed a tannery at Woolston. For much of the 12 years that Wood owned Glenmore, his wife Susan ran a private nursing home in the building. There is some speculation that it was Wood rather than Acland who built the two-storey portion of Glenmore.

The house was sold to the Glenmore Brick and Tile Manufacturing Company in 1905, to serve as a manager's residence. For much of the following thirty years, that position was filled by Thomas W. Woodroffe, apparently an able golfer and boxer. The brick veranda floor, terrace and balustrading are a legacy of this era.

In 1942 the brickworks went into liquidation, and Glenmore was sold with 1.2 hectares to advertising consultant Russell Thurlow Thompson. The house had become rundown during the later years of the brickwork's tenure, and apparently required much work to make it habitable again. Thompson was well-known for his work on behalf of Corso, and published an account of New Zealand's part in this organisation in 1965. In 1956 the house passed to his son, Richard H. T. Thompson, a reader in Sociology and Psychology at the University of Canterbury. Richard on-sold to family members David and Rachael Sturrock in 1992. The Sturrocks carried out alterations in 1993, extending the first floor over the 1850s portion to add three bedrooms to the existing five, and creating a new kitchen-living area.

The family passed Glenmore to developer Bill Horncastle in 1996. Horncastle applied for consent to subdivide the property into 17 sections, and notified the house for demolition. A public outcry ensued, with over 500 objections received by the Christchurch City Council. The house and half an acre were subsequently sold to saviours Lolly and John Fairweather, who carried out further renovation and restoration. The Fairweathers' operated Glenmore as home-stay accommodation until 2003, when it was sold to Penelope Wenlock and William Packard.