Grandora was established as a homestead in the early 20th century in what is now the Rural Municipality of Vanscoy No. 345, west of Saskatoon, Saskatchewan. The post office opened on June 2, 1908, under the name Diova in the electoral district of Saskatoon-Biggar. The name was changed to Glendora on February 15, 1910, before becoming Grandora, likely derived from the nearby Grand Trunk Pacific Railway station established as part of the railway's alphabetical naming scheme for sidings during its expansion across the prairies. Local lore attributes the name to a homesteading couple, with the husband reportedly exclaiming "Isn't it just grand, Dora?" to his wife upon arriving in the area. This anecdotal etymology reflects the personal and informal naming practices common among pioneers during the settlement period.

The founding of Grandora occurred circa 1905-1910, aligning with the peak of the homesteading boom in Saskatchewan driven by federal immigration policies. The Dominion Lands Act of 1872 offered 160-acre homesteads for a nominal fee to settlers, encouraging mass immigration to the Prairie provinces to develop agriculture and infrastructure. These policies, promoted aggressively by the Department of the Interior under Clifford Sifton, attracted over 1.5 million immigrants between 1896 and 1914, transforming the sparsely populated prairies into farming communities. Grandora's establishment exemplifies this era's rapid settlement patterns in central Saskatchewan.

The early settlement of Grandora, a small rural community west of Saskatoon in Saskatchewan's prairie region, accelerated in the early 20th century following the arrival of the railway and the establishment of essential community facilities. The post office opened on June 2, 1908, serving as a central hub for the growing number of homesteaders in the area. By 1911, the Grand Trunk Pacific Railway constructed a class E station in Grandora, facilitating transportation and further encouraging settlement along the line that extended across the prairies from 1905 to 1914. Local education needs were met through nearby one-room school districts, such as Bridgeford School District #2055 (later renamed Hawoods), located at SE Section 29, Township 36, Range 8 West of the 3rd Meridian, which operated from 1927 to 1960 to educate the children of farming families.

Immigration to the Grandora area during this period was part of the broader wave of British and European settlers drawn to Saskatchewan's fertile prairies for homesteading opportunities under the Dominion Lands Act of 1872, which allowed claimants to acquire 160-acre quarter-sections for a nominal fee after meeting residency and cultivation requirements. British immigrants, including those from England, Scotland, and Ireland, formed a significant portion of early arrivals, often settling in rural blocs suited to mixed farming; by the 1910s, non-British Europeans such as Germans and Scandinavians also contributed to the population through chain migration, with federal policies under Clifford Sifton actively recruiting them to develop the region's agricultural potential. These settlers were attracted by cheap land, railway subsidies, and promises of prosperity in grain production, transforming the native prairie into productive farmland.

The economic foundation of early Grandora rested on grain farming and mixed agriculture, well-adapted to the open prairie landscape. Wheat, particularly the early-maturing Marquis variety developed in 1904 and released in 1909, became the dominant crop, enabling reliable harvests in the short growing season and driving economic growth through exports via the expanding rail network. Farms typically combined grain cultivation—oats and barley for feed—with livestock rearing, including cattle, hogs, poultry, and horses for draft power, supporting household self-sufficiency and surplus sales; by 1921, Saskatchewan's cropped land had expanded to 17 million acres, with over 1 million horses powering operations. This mixed system was essential for rural stability, as settlers broke sod with plows and teams of oxen or horses, transitioning to gasoline tractors in the 1920s as prosperity allowed.

Early residents faced significant challenges, including the disruptions of World War I and the devastating 1918 influenza pandemic. The war (1914–1918) created labor shortages in rural areas as men enlisted, yet it also boosted demand for Saskatchewan grain, leading to record production and high prices that temporarily enriched farming communities despite the strain on families and resources. The Spanish flu, arriving in autumn 1918, struck rural Saskatchewan hardest, with over 5,000 deaths province-wide—many in isolated areas like those near Saskatoon—due to limited medical access, high pneumonia complication rates, and the closure of schools and gatherings under quarantine measures. In communities such as Grandora, the pandemic orphaned children, overwhelmed makeshift hospitals in schools and halls, and exacerbated post-war exhaustion, prompting calls for improved rural healthcare that influenced 1920s reforms.

Following the peak of settlement in the early 20th century, Grandora experienced a steady decline starting in the 1930s, driven by the economic hardships of the Great Depression and the associated "Dirty Thirties" dust storms, which led to widespread rural depopulation across Saskatchewan. Mechanization of agriculture in subsequent decades further diminished the demand for manual farm labor, accelerating outmigration from small communities like Grandora. After World War II, urbanization trends pulled remaining residents toward nearby Saskatoon for employment and services, contributing to the hamlet's contraction.

Key milestones in this decline included the closure of Grandora's school and post office during the 1950s and 1960s, reflecting broader patterns of rural service consolidation in Saskatchewan, where over 2,700 one-room schools shuttered between 1951 and 1971 due to low enrollment and centralization efforts. Mail services were subsequently redirected to the Sandyridge store along Highway 14, further eroding the community's infrastructure. These closures marked the end of Grandora's role as a self-contained rural hub, with the population dwindling as families relocated. Today, little of the original settlement endures, consisting primarily of scattered homes amid expansive farmland, a remnant of its former status as a more substantial "shadow town" tied to early railroad development. In the 2000s, minor residential growth occurred in the surrounding rural areas, fueled by Saskatoon's expansion and demand for affordable acreage living within commuting distance. This subtle revival has not restored Grandora's past vitality but has stabilized its presence as a quiet hamlet in the RM of Vanscoy.