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Before mid-century, Oak Bay's landscape was characterized overwhelmingly by single-detached dwellings. Few of these are Victorian-styled houses, but in older southern and central districts, most street blocks display a mix of hipped-roof, California, or Craftsman bungalows, two-storey eclectic cubes, and sometimes a fine Samuel Maclure designed Arts and Crafts cottage or four-square Colonial Revival. Fortunately, some of these are now protected by heritage bylaws. During the inter-war years of intensive infilling, 'minimal traditional' English Tudors (typically of one-and-a-half stories) became the architectural style of choice, seldom Art Deco or Art Moderne houses. By the 1950s, larger houses were favoured. Most were built in the low-slung ´rancher' style. This type predominates across north Oak Bay, including in the Uplands. More recently, an eclectic mix of even bigger neo-modernist styled dwellings has satisfied varied suburban tastes: Arts and Crafts revivals, mock Georgians, and flat-roofed cubes occasionally rub shoulders with 'po-mo' structures of ambiguous form.

Social change has affected the types of housing built in Oak Bay. After the Second World War, many of the large mansions found in south Oak Bay, especially those along Foul Bay Road, were converted into large suites. Older dwellings fronting bus routes and waterfront sites were torn down, making way for walk-up and high-rise apartments that offered units for rent. Some went to young couples, but most were taken-up by the recently-arrived widowed and retired set. A few projected housing plans were thwarted, including an early-1960s urban renewal scheme slated for Oak Bay's western flank, between the 'Avenue' and Cadboro Bay Road. Its intention was to replace the older, working-class housing of 'Poet's Corner' and nearby streets with town houses, garden apartments, and parkland, but came to naught.

Most of Oak Bay's street system was laid out in gridiron or quasi-gridiron fashion, with two notable exceptions. The first is the Uplands, a bourgeois subdivision of gracefully curving streets and large properties that occupies a waterfront and inland site of 465 acres (c.190 ha), almost one-fifth of Oak Bay's total domain. The Uplands was the first of its kind in Canada. It was designed in 1907 by the famous American landscape architect, John Charles Olmsted, for a land syndicate headed by the Winnipeg-based developer, William Hicks Gardner. On completion, John Olmsted identified the Uplands as his masterpiece of suburban residential design. The impact of the Uplands on Oak Bay has been profound, influencing, for example, subsequent zoning and town planning schemes that favoured bigger houses, which in turn drew in more middle-class people.

Breaking the grid, too, was a 620-acre (c.250 ha) property, once part of the Uplands Farm, that yielded three subdivisions and another Canadian first: Lansdowne Heights, Crestview Heights, and Lansdowne Park. Developed by the Hudson's Bay Company's Land Department from the late-1930s to the early-1960s, they formed the first town planning scheme in Canada to use the now-ubiquitous neighbourhood unit planning principles pioneered by Clarence Perry, an American sociologist. The Lansdowne Park component was originally designed to push beyond Cedar Hill Cross Road, ending at the Oak Bay - Saanich border, but its northward thrust was halted in 1961 when Victoria College (now the University of Victoria) bought 120 acres (c.48 ha) for use as part of its suburban Gordon Head campus.

Today, more than 15,000 undergraduate and graduate students are enrolled at UVIC; and the institution ranks among the top multi-purpose universities in Canada, offering a wide range of liberal arts, science, and professional programmes. Students come mostly from Victoria and the rest of Vancouver Island, less so from the Lower Mainland and interior British Columbia. Increasing numbers of students now hail from Asia and South America, adding diversity to Oak Bay's cultural mosaic.

While small parts of UVIC's campus remain in their former orchard, pasture, or forest state, Oak Bay's largest (and almost) natural area of treed and grassy space is Uplands Park, a 76-acre tract carved from the Uplands subdivision in 1946. On its grounds, fronting Beach Drive, a Cenotaph celebrates Oak Bay's fallen war heroes. A short walk away, the Esplanade, developed in the 1950s, links Uplands Park with Willows Park, Oak Bay's oldest (estab. 1912) and a place for public celebrations. There are more than twenty other parks scattered throughout the municipality. Most are quite small, but some are slightly larger, including Carnarvon, located on the site of the old Exhibition Grounds; and Walbran, sitting atop Gonzales Hill near the old Dominion Observatory. These two parks offer venues, respectively, for playing organized sports or for looking over Oak Bay in its entirety.

Yes, there is much to see when exploring the historic pathways of Oak Bay. The making of Oak Bay's distinctive suburban landscape offers a record of accomplishment to be considered and enjoyed by resident and visitor alike.