Winston Park
Your comprehensive guide to Winston Park, Oakville, Ontario
SAFETY RATING
9.5 / 10Very Low Crime Risk
View full crime analytics & trends →
Property Pulse
$6,834,700 Avg List
Solid inventory of detached family houses and townhomes.
Community Canvas
213,759 Residents
Rich tapestry of families, kids under 10, and professionals.
What You'll Love
Parks & Schools
High academic rankings and beautiful outdoor spaces.
Local Active Listings
Browse active properties for sale in this area.
Benefits of Browsing Just Listed Properties in Winston Park, Oakville
When searching for a home in Oakville, timing is everything. Accessing fresh MLS® listings the moment they hit the market gives home buyers a critical competitive advantage in Ontario's fast-moving real estate market.
First-Mover Advantage
Be the first to view new listings in Oakville within minutes of MLS® publication before competing buyers schedule viewings.
Motivated Sellers
Newly listed sellers are eager to receive serious offers and negotiate terms before setting offer dates.
Avoid Multiple Offers
Early inquiries allow proactive buyers to submit strong pre-emptive offers before bidding wars escalate prices.
Accurate Price Valuation
Compare initial asking prices against recent Oakville sold data to spot underpriced gems immediately.
Explore Winston Park
Winston Park is one of Oakville's most sought-after communities, offering a perfect balance of suburban tranquility and urban convenience. Located in the heart of Oakville, this family-friendly neighbourhood is known for its tree-lined streets, spacious detached homes, and well-maintained townhouses, making it ideal for growing families, young professionals, and retirees alike. The community boasts excellent transit options, with Oakville Transit bus routes connecting directly to Bronte GO Station, providing seamless commutes to Toronto via the GO Train. Residents enjoy a relaxed lifestyle with access to multiple parks, including the sprawling Winston Park, which features sports fields, playgrounds, and scenic walking trails. For everyday shopping and dining, the nearby Oakville Place and various strip malls along Upper Middle Road offer everything from boutique shops to popular eateries. With its strong sense of community, proximity to top-rated schools, and easy highway access at QEW and Highway 403, Winston Park stands out as a prime choice in Oakville's dynamic real estate market. Whether you're seeking a peaceful retreat or a well-connected hub, Winston Park delivers both, ensuring a high quality of life for all who call it home.
For a local secret, head to the 'Three Creeks' trailhead tucked behind St. Matthew's Catholic Elementary—it's a hidden gem for nature walks that connects to the larger trail network. If you're a coffee lover, skip the chain spots and visit 'Coffee Culture' on Upper Middle Road, where the baristas know your name and the patio is perfect in summer. For an afternoon out, hit 'Joshua's Garden' (a few minutes drive) for seasonal veggies and artisanal goods—locals grab their pumpkins here in October. Early risers should try the 'Valley View Golf Club' for a quiet morning round, a laid-back course that often has locals-only deals. Steer clear of the area around Bronte GO during rush hour if possible—it's congested. Always check for open house events at local schools; they often host community pancake breakfasts where you can a feel for neighbours.
Home Prices & Values in Oakville
The asking price of homes for sale in Oakville has decreased 1.68% since last year, while the number of homes for sale has increased 5.8%. See more Oakville Home Prices & Values.
Find Real Estate & MLS® Listings in Oakville
SousaSells.ca has the most thorough, up-to-date set of Oakville real estate listings. Currently, Oakville has 1208 homes for sale, including 682 houses, 277 condos, and 0 townhouses listed for sale. The average price for all home types in Oakville is $1.9M, which is up 3.5% compared to last year.
Oakville is home to 50 unique neighbourhoods. With SousaSells.ca you'll be able to find the hottest Oakville neighbourhoods, the best schools in the city, and evaluate nearby amenities. Check out the upcoming open houses in Oakville to tour homes in person. Narrow down your home search to filter by price, bedrooms, size or search by our map of MLS® listings for Canada-wide real estate.
MLS® Listing data for Oakville is updated every 15 minutes to provide you the most-up-to-date home listings. Get in touch with one of our Oakville real estate agents to get started on landing your dream home today.
Median Age
The median age of residents in this area.
Home Ownership
Percentage of owner-occupied households.
Neighborhood Safety & Crime Analytics
Winston Park, Oakville
8 assaults (45.0/100k)
8 B&E (40.0/100k)
12 thefts (45.0/100k)
Improving vs previous year
Formula: (Annual Occurrences / Population) × 100,000. This standard policing calculation normalizes incident frequencies across different population sizes, allowing accurate safety comparisons between quiet residential pockets and dense urban centres.
Disclaimer: Crime and safety analytics are compiled from official municipal and regional police open data records for general consumer informational and demographic research purposes only. Data is deemed reliable but is not guaranteed and does not constitute a legal representation or guarantee of future safety.
People & Families
Demographics, age distribution, household size and makeup.
Age Demographics (Detailed Ranges)
Household Composition
Ethnic Origins
Local Schools
Ratings, ranking and classification of elementary and secondary schools.
Elementary Schools
St Marguerite d'Youville
1359 Bayshire Drive, Oakville, Ontario, L6H 6C7
Holy Family
1420 Grosvenor Street, Oakville, Ontario, L6H 2X8
Falgarwood
1385 Gainsborough Drive, Oakville, Ontario, L6H 2H7
St Matthew's
Matthew Street, Oakville, Ontario, L6H 2R9
Post's Corners
2220 Caldwell Drive, Oakville, Ontario, L6H 6B5
St Luke
2750 Kingsway Drive, Oakville, Ontario, L6J 7G5
James W. Hill
2860 Kingsway Drive, Oakville, Ontario, L6J 6R3
Joshua Creek
Oakville, Ontario, L6J 7S2
St Andrew
145 Millbank Drive, Oakville, Ontario, L6H 6G3
Montclair
1285 Montclair Drive, Oakville, Ontario, L6H 1Z3
St. Gregory the Great
138 Sixteen Mile Drive, Oakville, Ontario, L6M 0T7
Secondary Schools
Iroquois Ridge
1123 Glenashton Drive, Oakville, Ontario, L6H 5M1
Gaétan Gervais
1075 McCraney Street East, Oakville, Ontario, L6H 1H9
Holy Trinity
2420 Sixth Line, Oakville, Ontario, L6H 5Z8
White Oaks
Onslow Court, Oakville, Ontario, L6H 1H9
Homes & Housing
Ownership rates, home structure distributions and listing prices.