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 4thbedroom, 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.
Address
44 Head Street
List Price
$2,299,000
MLS® Status
New
Expiration Date
2026-06-30
Property Type
Residential Freehold
Type of Dwelling
Detached
Style of Home
2-Storey
Transaction Type
Sale
Area
Oakville
Sub-Area
1002 - CO Central
Region
Halton
Bedrooms
3 + 1
Bedrooms (Total)
4
Rooms Above Grade
7
Rooms Below Grade
3
Bathrooms
5
Floor Area
2000-2500 Sq. Ft.
Lot Size Source
MPAC
Lot Depth
104.33
Lot Size Units
Acres
Lot Width
40
Parcel Number
248190071
Occupant Type
Owner
Cross Street
Wilson and Rebecca
Approx. Age
6 - 15 Years
MLS® Number
W12826420
Listing Brokerage
RE/MAX ABOUTOWNE REALTY CORP.
Basement Area
Full, Finished
Postal Code
L6K 1L5
Posession Details
Flexible
Parking Places (Total)
7
Parking Spaces
6
Tax Amount
$9,999.00
Tax Year
2025
Site Influences
Electric Car Charger, Fenced Yard, Patio, Porch, Public Transit
Exterior Features
Porch, Patio
Interior Features
Central Vacuum
Property Features
Electric Car Charger, Fenced Yard, Public Transit
Central Vacuum
Yes
Family Room
Yes
Ensuite Laundry
No
Special Designation
Unknown
Standard Status
Active
Board Or Association
Toronto Regional Real Estate Board
Heat Source
Gas
Heat Type
Forced Air
Cooling Features
Central Air
Construction Materials
Wood
Direction Faces
South
Fireplace
Yes
Fireplace Features
Natural Gas
Foundation Details
Poured Concrete
Garage
Yes
Garage Type
Detached
Covered Spaces
1
Kitchens Total
1
Kitchens Above Grade
1
Pool Features
None
Roof
Asphalt Shingle
Tax Legal Description
PT LT 7, BLK 95, PL 1, AS IN 526751. TOWN OF OAKVILLE
Waterfront
No
Sewer
Sewer
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Rooms
| Floor | Type | Dimensions | Features |
|---|---|---|---|
| Main | Great Room | 4.9 x 3.94 | Fireplace, Hardwood Floor, Walk-Out |
| Main | Dining Room | 4.9 x 2.74 | Hardwood Floor, Walk-Out |
| Main | Kitchen | 5.44 x 3.94 | Centre Island, Granite Counters, Hardwood Floor |
| Main | Office | 3.89 x 4.5 | French Doors, Hardwood Floor |
| Main | Bathroom | 1.12 x 1.47 | 2 Pc Bath |
| Second | Primary Bedroom | 3.99 x 4.5 | 4 Pc Ensuite, Walk-In Closet(s) |
| Second | Bathroom | 2.51 x 2.82 | 4 Pc Ensuite, Heated Floor, Soaking Tub |
| Second | Bedroom 2 | 4.37 x 3.25 | 3 Pc Ensuite, Walk-In Closet(s) |
| Second | Bathroom | 1.83 x 2.11 | 3 Pc Ensuite, Heated Floor |
| Second | Bedroom 3 | 5.23 x 5.69 | 4 Pc Ensuite, Walk-In Closet(s) |
| Second | Bathroom | 2.46 x 1.52 | 4 Pc Ensuite, Heated Floor |
| Lower | Recreation | 5.23 x 4.42 | Pot Lights |
| Lower | Bedroom 4 | 6.32 x 4.42 | |
| Lower | Bathroom | 1.45 x 3.1 | 3 Pc Bath |
| Lower | Laundry | 2.62 x 3.05 |
Open Houses
- March 08, 2:00 PM - 4:00 PM