44 Head Street, Oakville, ON L6K 1L5, Oakville, ON
Bed 4
Bath 5
Welcome to 44 Head St - an exceptional home in the heart of Oakville- steps from Kerr Village & downtown. Enjoy walkable access to local shops, dining & the lakefront-the perfect blend of convenience & tranquility. Offering almost 2200 sq ft plus fully finished basement ( 1015 sq ft), this remarkable residence offers timeless charm & modern functionality. Set behind pretty gardens, the Dark Slate wood siding & crisp white trim frame an inviting front porch-perfect for morning coffee or evening wine. Inside, 9' ceilings, hardwood floors, crown moulding & high baseboards create a refined, elevated feel. The entertainer's kitchen showcases granite countertops, a large island, professional-grade appliances & generous storage, seamlessly flowing into the bright, open-concept living & dining areas. A cozy gas fireplace with custom millwork adds warmth, while French doors lead to the beautifully landscaped rear garden-perfect for relaxing or hosting outdoors. A versatile room on the main floor can serve as your personal office or den; it could also be transformed into a separate dining room if desired. Upstairs are 3 spacious bedrooms, each with ensuites with heated floors & walk-in closets . The lower level (9' ceilings) includes a spacious family room plus 4th bedroom, 3pc bath & large laundry room. Storage is no issue in this home with the many custom built-in closets & cabinets. A detached garage with EV charger features a rare basement for even more storage! Plus there is parking for 6 cars on the extra long driveway. A fully fenced private rear yard, & unbeatable walkability to parks, shops, cafés & the waterfront make this turnkey property a rare offering. Meticulously maintained by the current owners, recent updates include powder room renovation (2024), driveway resurfaced (2024), exterior newly stained (2024) & insulation upgraded to R60 (2025). Ideal for empty nesters, downsizers & families. Don't miss this opportunity to experience Oakville's historic charm.
Property Highlights
For Sale
MLS NO.
W12826082
Type
Residential Freehold
Sub Type
Detached
Bedrooms
4
Bathrooms
5
Parking
7.0
Garage
Yes
Complete Property Details
Property Type
Residential Freehold
Sub Type
Detached
Transaction Type
For Sale
Status
Cancelled
Contract Status
Unavailable
MLS® Number
W12826082
Living Area Range
2000-2500
Total Bedrooms
4
Bedrooms Above Grade
3
Bedrooms Below Grade
1
Total Bathrooms
5
Total Kitchens
1
Kitchens Above Grade
1
Rooms Above Grade
7
Rooms Below Grade
3
Interior Features
Central Vacuum
Fireplace
Yes
Fireplace Features
Natural Gas
Central Vacuum Yn
Yes
Construction
Wood
Roof
Asphalt Shingle
Lot Width
40.0
Lot Size
0.1
Parking Total
7.0
Covered Spaces
1.0
Garage Type
Detached
Garage
Yes
Pool
None
Direction Facing
South
Cooling
Central Air
Heat Source
Gas
Heat Type
Forced Air
Internet Address Display Yn
Yes
Internet Entire Listing Display Yn
Yes
Full Address
44 Head Street, Oakville, ON L6K 1L5
City
Oakville
Neighbourhood
1002 - CO Central
County / Region
Halton
Province / State
ON
Postal Code
L6K 1L5
Cross Street
Wilson and Rebecca
Directions
Rebecca to Wilson to Head St
Country
CA
List Price
$229,900,000
Annual Taxes
$9,999
Tax Year
2025
Legal Description
PT LT 7, BLK 95, PL 1, AS IN 526751. TOWN OF OAKVILLE
Possession Type
Flexible
Possession Details
Flexible
Listing Office
RE/MAX ABOUTOWNE REALTY CORP.
Board
Toronto Regional Real Estate Board
Original Entry
2026-02-27T14:15:21Z
Media Updated
2026-02-27T14:15:21Z
Photos Updated
2026-02-27T14:15:21Z
Last Modified
2026-02-27T14:59:03Z
System Modified
2026-02-27T14:59:13.359982Z
MLS Status
Terminated
Architectural Style
2-Storey
Basement
Full, Finished
Co List Office Name
RE/MAX ABOUTOWNE REALTY CORP.
Ddfyn
Yes
Expiration Date
2026-06-30
Foundation Details
Poured Concrete
Heat Source Multi
Gas
Heat Type Multi
Forced Air
Hstapplication
Included In
Link Yn
No
Occupant Type
Owner
Originating System Id
A00001796
Parcel Number
248190071
Parking Spaces
6
Property Features
Electric Car Charger, Fenced Yard, Public Transit
Public Remarks
Welcome to 44 Head St - an exceptional home in the heart of Oakville- steps from Kerr Village & downtown. Enjoy walkable access to local shops, dining & the lakefront-the perfect blend of convenience & tranquility. Offering almost 2200 sq ft plus fully finished basement ( 1015 sq ft), this remarkable residence offers timeless charm & modern functionality. Set behind pretty gardens, the Dark Slate wood siding & crisp white trim frame an inviting front porch-perfect for morning coffee or evening wine. Inside, 9' ceilings, hardwood floors, crown moulding & high baseboards create a refined, elevated feel. The entertainer's kitchen showcases granite countertops, a large island, professional-grade appliances & generous storage, seamlessly flowing into the bright, open-concept living & dining areas. A cozy gas fireplace with custom millwork adds warmth, while French doors lead to the beautifully landscaped rear garden-perfect for relaxing or hosting outdoors. A versatile room on the main floor can serve as your personal office or den; it could also be transformed into a separate dining room if desired. Upstairs are 3 spacious bedrooms, each with ensuites with heated floors & walk-in closets . The lower level (9' ceilings) includes a spacious family room plus 4th bedroom, 3pc bath & large laundry room. Storage is no issue in this home with the many custom built-in closets & cabinets. A detached garage with EV charger features a rare basement for even more storage! Plus there is parking for 6 cars on the extra long driveway. A fully fenced private rear yard, & unbeatable walkability to parks, shops, cafés & the waterfront make this turnkey property a rare offering. Meticulously maintained by the current owners, recent updates include powder room renovation (2024), driveway resurfaced (2024), exterior newly stained (2024) & insulation upgraded to R60 (2025). Ideal for empty nesters, downsizers & families. Don't miss this opportunity to experience Oakville's historic charm.
