The area is bordered by the Assiniboine River on the north and west, Harkness Station on the east, and the Osborne Underpass on the south.

[3] In the 20th century, Osborne Village's Roslyn Road was developed as a wealthy residential enclave, and by 1911, it was home to the mansions of Winnipeg families.

[5] In 2011, the Shoppers Drug Mart at 43 Osborne Street proposed a plan to purchase the neighbouring building to permit its expansion.

[7] Citing the threatened loss of two local businesses, Movie Village and Vi-Ann, a Vietnamese restaurant, area residents raised a campaign to appeal and block the purchase, collecting over 4,000 signatures,[8] but the purchase plans were upheld by a city appeals committee in February 2012.

[1][11] Osborne Village has Winnipeg's tallest residential building outside of the downtown core: 55 Nassau Street North.

[12] Winnipeg Transit routes that cross through the Village are: 16 Osborne-Selkirk, 18 North Main-Corydon, 60 Pembina, 68 Grosvenor and 635 Misericordia Centre (Replace 99 and 185).

[15] The two-day festival featured live music stages, food vendors, artisan booths, and kids' activities.