366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
366 Winston Churchill Boulevard
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43 photos

366 Winston Churchill Boulevard

Ford, Oakville, ON
Listed 23 days ago
$1,585,000For Sale
$1,432,736Estimated value
3Bedrooms
3Bathrooms
1500-2000 sqftSize
6 (1 garage)Parking
100 ft × 177 ftLot Size
DetachedProperty Type

366 Winston Churchill Boulevard

Oakville, ON · Ford

Listed 23 days ago
Bedrooms3
Bathrooms3
Size1500-2000 sqft
Parking6 (1 garage)
Lot Size100 ft × 177 ft
Property TypeDetached
$1,585,000
For Sale
MLS# W13241874
$1,432,736Estimated value

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About this home

Welcome to this beautiful ravine home, located in prestigious south east Oakville, just steps from Lakeshore Rd and a short walk to Lake Ontario! Surrounded by mature trees on a large 100 X 177 foot lot, this spacious 3 + 1 Bedroom, 3 bathroom home offers exceptional ravine views via multiple rooms throughout the home. Featuring a separate entrance, and a lower level with with over 7 1/2 foot ceilings that has a walkout to a serene natural backyard! Enjoy outdoor living from the privacy of the upper deck or the lower patio. Situated close to spectacular parks along the waterfront, the Southeast Sports Field, the waterfront trail, and a short scenic drive to downtown Oakville! Appreciate the easy highway access, excellent schools nearby and the short drive to the Clarkson GO!

Features & Details

Property Type
Detached
Tax
$7,327 / 2026
Building Age
51-99 years
Size
1500-2000 sqft
Lot Size
100 x 177 Feet
Basement Info
Finished with Walk-Out
Total Parking Spaces
6 (1 Garage)
Title
Residential Freehold
Property Style
Bungalow
Community
Ford
Municipality
Oakville
Construction
Aluminum Siding
Cross Street
Winston Churchill Blvd/Lakeshore Rd W
Front Door Facing
West
Lot Legal Description
PT LT 1, CON 3 TRAFALGAR, SOUTH OF DUNDAS STREET , AS IN 788857, T/W 788857 ; S/T THE RIGHTS OF OWNERS OF ADJOINING PARCELS, IF ANY, UNDER 652094 ; OAKVILLE/TRAFALGAR
Data Source
Toronto Regional Real Estate Board
Brokerage
RE/MAX REALTY ENTERPRISES INC.
Listed On
Jun 04, 2026
Listing Expires On
Sep 30, 2026
Listing Updated On
Jun 14, 2026
Bedrooms
3
Bathrooms
3
Kitchens
1
Rooms
7
Bathroom Detail
3 Pcs on Ground Level
Bathroom Detail
4 Pcs on Ground Level
Bathroom Detail
3 Pcs on Basement Level
Driveway
Private
Garage Type
Attached
Garage
1
Parking
6
Heating
Forced Air
Heat Source
Oil
Cooling
Central Air
Sewer
Septic
Den / Family Room
Yes
Fireplace
Yes
Swimming Pool
None
Roof Material
Asphalt Shingle
Foundation Type
Concrete Block
Interior Features
Water Heater, Water Meter

Listing History

Active23 days on marketCurrently viewingMLS #W13241874
Jun 4, 202624 days ago
Listed for Sale
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This is the only listing record currently available for this property.

Estimate History

Estimated value, last 24 months
Jul 2024 – Jun 2026
$1.51M
$1.4M
$1.28M
$1.17M
Jul
Dec
May
Oct
Mar
Jun

Automated estimate from Polsinello Predictive AI. Not an appraisal. Actual market value may differ.

Mortgage calculator

Estimated monthly payment
$7,732

Estimated payment. Does not include property tax, insurance, or condo fees.

Location & nearby

Ford Real Estate Market

Oakville · last 90 days
$1,900,000
Median sold price
33 days
Avg days on market
27
Homes sold (90 days)
30%
Sold above asking
70%
Sold below asking
$860–$1,121/ft²
Price per sq ft
Median price trend
Jul 2025 – Jun 2026
$2.45M
$2.11M
$1.76M
$1.42M
Jul
Oct
Jan
Apr
Jun

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