Because of it 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 Headingley'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 Nursuries, a premier garden center for the capital region around Winnipeg, is one of the municipalities more prominent employers, employing approximately 40 local residents. Taillieu Construction, a heavy equipment construction specialist, also employs approximately 40 residents. Green Gates Restaurant and the Husky Service Station and Restaurant employ approximately 20 staff.

The Breezy Bend Country Club, and John Blumberg Golf Course and Softball complex are also prominent employers, with their approximately 50 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. An insurance agent, credit union, accountant, financial planning, convenience stores, and several restaurants, and a k-8 elementary school are just some of the services the town boasts. For a larger range of services residents must travel to nearby Winnipeg.