
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 The Oaks
The Oaks sits just west of Winnipeg, alongside Monterey Park and Headingley North, and these are newer estate-style developments rather than older city streets. The Oaks itself is known for detached bungalows built under a condominium ownership structure, which suits people who want a single-level home without the yard work and exterior upkeep. Monterey Park and Headingley North lean toward larger, newer single-family homes on spacious lots. The overall feel is fresh and low-density.
A separate municipality, worth knowing
Here is the part buyers sometimes miss. The Oaks and its neighbours are in the Rural Municipality of Headingley, not the City of Winnipeg. That is a different municipality with its own property taxes, its own services and its own rules. Some properties at the city's edge run on well and septic rather than full city services, so confirm which applies. It is worth understanding before you buy, because it affects your ongoing costs. The Trans-Canada Highway and Roblin Boulevard put you into Winnipeg's west side and its shopping quickly.
Buying and selling here
On a bungalow condo in The Oaks, read the condominium documents closely: the monthly fees, what they cover, the reserve fund and the rules. On a Monterey Park or Headingley North home, confirm the services situation, check the lot grading and drainage, and on a newer build ask about any remaining New Home Warranty. Selling here, the single-level low-maintenance living, or the space and newer construction, are the features to lead with.
Common Questions About This Community
Is The Oaks in Winnipeg?
No. The Oaks, Monterey Park and Headingley North are in the Rural Municipality of Headingley, just west of the city, with their own taxes and services.
What kind of homes are here?
The Oaks is known for detached bungalows under a condominium ownership structure; Monterey Park and Headingley North have larger newer single-family homes on spacious lots.
What does the condo ownership mean?
You own a detached bungalow but pay condo fees for shared upkeep such as exterior and grounds maintenance, so review the corporation documents.
What should I check here?
The Headingley taxes and services, whether the home is on city services or well and septic, and the condominium documents where they apply.

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:

