Shaughnessy Heights was once part of District Lot 526, a 2,428 hectare land grant assigned to CPR officials Donald Smith and Richard Angus in 1885 but later transferred to the direct control of the railway. For many years the CPR did little with this vast domain which was too far from the Vancouver townsite to have much value as real estate. The company set aside a small area of land to grow vegetables and flowers for its hotels and transcontinental trains and, in 1888, helped to finance the construction of the North Arm Road, later Granville Street, south to the Fraser River. In the early 1900s the CPR began to sell lots in the Fairview and Kitsilano districts at the English Bay end of District Lot 526. To the south, beyond 12th Avenue, was a wasteland covered by brush and tree stumps.

In 1907 Richard Marpole, general superintendent of the CPR, announced that the company planned to create an exclusive suburb for Vancouver's upper class citizens on the hilly slopes south of False Creek. The Montreal landscape architect Frederick Todd and his assistant, L.E. Davick, a Danish engineer, were placed in charge of the $2 million project which was to include such amenities as a lawn bowling club, golf course and tennis courts. The design of Shaughnessy Heights reflected Todd's enthusiasm for the "garden city" concept of urban landscaping. The homes of the rich were surrounded by hedgerows and broad lawns. Tree-lined boulevards followed the contours of the local terrain, ascending to the Crescent, a circular drive of expensive property situated on the highest ground in the neighborhood.

In the summer of 1909 an army of 1200 workers began to cut roads, build sidewalks and lay sewer lines in the 101 hectare CPR fiefdom. When the first lots went on sale a year later Vancouver's wealthier citizens were quick to abandon their former haunts in the West End. By 1914 there were 243 households in Shaughnessy Heights, 80 per cent of which were listed in the Vancouver social register.

The pre-World War I "golden age" of Shaughnessy Heights home construction included a variety of architectural styles: 18th century Georgian townhouses, Spanish colonial haciendas, federal style homes, Cape Cod cottages and oversized California bungalows. The favored society architects of the period were Samuel Maclure of Victoria and his Vancouver partner C.C. Fox, designers of such classic Tudor revival homes as Rosemary, constructed in 1913 at 3689 Selkirk for A.E. Tulk, a distillery owner. Tulk named his mansion after his only daughter but most early Shaughnessyites gave their homes whimsical names such as the British gentry might have preferred: Bonnie Blink, Welcome Holme, Greyshott, Glen Brae, Grey Gables, Greencroft.

By 1920 the society pages of Vancouver newspapers were an intimate chronicle of the lives of Shaughnessy residents as they moved through an endless whirl of balls, dances, yacht parties, charity meetings and afternoon teas. Social standing in "CPR Heaven" was often determined by the status of the guests invited to one's home, at Ardor, Maj. Gen. "Jack" Stewart, a railway contractor with political connections, was host to such notables as the Dukes of Windsor and Kent; Misak Aivazaoff, a Russian émigré, entertained the pianist Sergei Rachmaninoff and members of the dispossessed Russian nobility in Villa Russe at 3390 the Crescent.

In the early '20s the high point of the Shaughnessy social Calendar was the New Year's Eve costume ball at Hycroft, residence of Gen. Alexander Duncan McRae, the multi-millionaire cannery owner. Built in the style of a palatial ante-bellum Southern mansion, Hycroft was famous for its downstairs ballroom where the floorboards were packed with dried seaweed to give dancers greater bounce. (Glen Brae has a similar floor.) On the grounds outside were three gardens, an enormous greenhouse, riding stables, tennis courts and a guest house. The interior of the mansion reflected General McRae's aristocratic tastes with a wine cellar, mirrored bar and a variety of dens, drawing rooms and solaria. The general's household servants went about their work in hidden passageways that ran parallel to the McRae family's well-appointed quarters.

Shaughnessy Heights was developed in three stages over a twenty-year period. Most of the lots in so-called First or Old Shaughnessy, extending from 16th Avenue to King Edward Ave., were sold by 1914. By then work crews were clearing the land south to 37th Avenue for Second Shaughnessy, which was completed in 1929. The expansion into Third Shaughnessy, between King Edward and 41st Avenue, did not begin until 1926.

In the early stages of Shaughnessy Heights' development the CPR took steps to assure that the provincial legislature, rather than the Municipality of Point Grey, controlled local zoning regulations—an arrangement made possible by the unusual number of political and financial leaders who resided in the neighborhood. In 1911 the British Columbia legislature passed the frrst local zoning law followed in 1922 by the Shaughnessy Heights Building Restriction Act which prohibited the division of single family dwellings into apartments or housekeeping rooms. Most CPR deeds of sale contained their own single-family clauses as well as restrictive covenants forbidding the re-sale of property to Jews and Orientals.

During the Depression years the homes of many Shaughnessy Heights residents were either repossessed by the CPR or placed on the market for a fraction of their original value. (Cynical observers referred to the once affluent neighborhood as Poverty Hill and Mortgage Heights,) Appraised at $75,000 in 1920, Glen Brae, the William Lament Tait mansion at 1690 Matthews, sold in 1939 for $7,500 and was later used as a kindergarten and nursing home. Today this ornate old mansion has been transformed into Canuck Place, a hospice for children. Rosemary was turned into a convent. Hycroft became a military hospital.

In 1942 wartime housing shortages prompted the federal government to issue an order-in-council allowing Shaughnessy homes to be split up into smaller units. In 1955, when the order-in-council expired, the Shaughnessy Heights Property Owners' Association led the campaign to return to the pre-war period of single family homes. Eventually the provincial government decided that it would not change the status of existing multiple family dwellings but that any properties that lapsed into single family use for more than a month would be zoned that way permanently.

Despite the complaints of local residents, Vancouver real estate developers showed little reluctance to break up the old manorial properties, a process made easier when the provincial building restriction legislation expired in 1970. In19375 the CPR constructed condominiums and townhouses on the former Shaughnessy Golf Course, setting aside 22 hectares for the VanDusan Botanical Gardens.

According to the federal census of 1991 the average household income in Shaughnessy Heights declined by 10 per cent between 1980 and 1990 from $112,106 to $102,933. (During the same period, average Vancouver household incomes rose by 4.5 per cent.)

In 1991, 58 per cent of Shaughnessy Heights residents had a university education compared to 34 per cent in Vancouver as a whole. Seventy-six per cent owned their homes (40 per cent in Vancouver). In 1991 it cost $913 to rent the average Shaughnessy Heights apartment ($707 in the rest of the city).

The population of Shaughnessy Heights remained static during the 1980s; there were 9,345 residents in 1981; 9,035 in 1991—a decline of 3.3 per cent. From 1980 to 1990 Shaughnessy Heights witnessed a 25 per cent drop in the number of residents under the age of 25 and a 55 per cent increase among people in their early 40s—a possible demographic effect of the aging baby-boom population.