Because of its proximity to Winnipeg, Headingley boasts big city amenities and services, yet provides residents with a slower paced, intimate community life. Hospitals, large shopping centers, and a wide range of professional services are a quick drive from Headingley.

One of Headingly’s biggest advantages is its low residential tax and no business tax. This makes Headingley a very attractive place to live and set up businesses. The community is an ideal place for businesses to locate, since it draws upon its location.

The community itself has many successful businesses that employ local residents. Shelmerdine's Nurseries,Taillieu Construction,The Gates on Roblin, T&T Seeds, Flying J,Husky are only a handful of our many businesses in Headingley The Breezy Bend Country Club, and John Blumberg Golf Course and Softball complex are also prominent employers, with their staff employed in various positions as managers, groundskeepers and restaurant staff.

Headingley itself has a wide range of local business that meets the community's needs. Insurance, credit union, accountants, financial planning, convenience stores, and several restaurants,contractors and a k-5 elementary school are just some of the services the town boasts.