
Description
Houses for sale in Headingley North, Monterey Park, and The Oaks, near Winnipeg have communities that form part of a greater city area, considered St James/Assiniboia. It is a place that has no shortage of shops, restaurants, and a mix of rather quaint neighbourhoods that run either toward the Assiniboine River, and are thereby more pricey, or further north into nice quite streets that are studded with parks. The area is thus a mix of affluence, particularly in the St. Charles Country Club area around the river, to middle class, to more working class in the areas in and around the Winnipeg Airport. These neighbourhoods form MLS® area 5W.
Homes in Headingley North
Headingley North is on the western edge just outside Winnipeg, and here is the key thing: it is in the Rural Municipality of Headingley, not the city. The housing is mostly single-family homes on larger lots, with a semi-rural feel and real space, and some genuinely sought-after riverfront and treed acreage properties along the Assiniboine. It suits buyers who want room and a country-adjacent setting within an easy drive of town.
Space, trees and the river
This is a quiet, spread-out area valued for its trees, river access and trails. It is greener and more private than a city subdivision, which is the whole point for the people who buy here. Downtown Winnipeg is roughly a 20-to-25-minute drive, so you get the space without being cut off.
Buying in Headingley: what changes
Because Headingley is a separate municipality, confirm the property taxes and how services work for any home, they are not Winnipeg's. Many properties out here run on a private well and septic rather than city water and sewer, so check what a home has, and its age and condition. On riverfront or treed acreage, look at drainage, the riverbank, flood history and road access, and confirm permits on any outbuildings. Do the homework and it is a great place to land.
Common Questions About This Community
Is Headingley North in Winnipeg?
No, it is in the Rural Municipality of Headingley, just west of the city, with its own taxes and services.
What kind of homes are here?
Mostly single-family homes on larger lots, with some riverfront and treed acreage along the Assiniboine.
Are homes on city services or well and septic?
Many run on a private well and septic, so confirm for the specific property.
What should I check on a riverfront or acreage property?
Taxes and services, well and septic, drainage, the riverbank and flood history, road access, and permits for outbuildings.

Amenities
🚌 Transit
No regular transit routes in this area
🏥 Nearest Hospital
📚 Library
Westwood Library
🌳 Parks & Recreation
John Blumberg Park, The Oaks Forest, The Oaks Path — Find Winnipeg Parks →
Real Estate Statistics
The total units of single family detached homes sold in
School Information
School divisions generally include multiple MLS® areas. Other schools within the same school division may also serve this area and the following schools are within this MLS area:

