44 Head Street Oakville, Ontario L6K 1L5
$2,299,000
Welcome to 44 Head St—an exceptional residence in the heart of Oakville—just steps to Kerr Village, downtown boutiques, cafés & the lakefront. Here, vibrant walkability meets peaceful, tree-lined charm. Offering nearly 2,200 sq ft above grade + a fully finished 1,015 sq ft lower level, this timeless home blends character with modern comfort. Set behind manicured gardens, dark slate wood siding & crisp white trim frame a welcoming front porch—perfect for morning coffee or evening wine. Inside, 9' ceilings, hardwood floors, crown moulding & high baseboards create an elevated aesthetic. The entertainer’s kitchen features granite countertops, a generous island, professional-grade appliances & abundant storage, flowing seamlessly into bright, open-concept living & dining spaces. A gas fireplace with custom millwork anchors the room, while French doors open to a beautifully landscaped, private rear garden—ideal for relaxing or hosting al fresco. A versatile main-floor room offers flexibility as a home office, den or formal dining room. Upstairs, 3 spacious bedrooms each enjoy their own ensuite with heated floors & walk-in closets—luxury & privacy for all. The lower level with 9' ceilings adds a large family room, 4th bedroom, 3-pc bath & expansive laundry room. Custom built-ins throughout provide exceptional storage. The detached garage includes an EV charger & rare basement storage, while the extra-long driveway accommodates 6 cars. The fully fenced backyard offers a private garden with pretty perennials as well as a stone patio. The unbeatable location places parks, shops, restaurants & the waterfront at your doorstep. Meticulously maintained with thoughtful updates: powder room renovation (2024), driveway resurfaced (2024), exterior freshly stained (2024) & insulation upgraded to R60 (2025). Ideal for empty nesters, downsizers & families alike—this turnkey home is a rare opportunity to experience Oakville’s historic charm at its finest. (id:63008)
Open House
This property has open houses!
2:00 pm
Ends at:4:00 pm
Property Details
| MLS® Number | 40808082 |
| Property Type | Single Family |
| AmenitiesNearBy | Park, Shopping |
| CommunityFeatures | Quiet Area |
| EquipmentType | Water Heater |
| Features | Paved Driveway, Sump Pump, Automatic Garage Door Opener |
| ParkingSpaceTotal | 7 |
| RentalEquipmentType | Water Heater |
| Structure | Porch |
Building
| BathroomTotal | 5 |
| BedroomsAboveGround | 3 |
| BedroomsBelowGround | 1 |
| BedroomsTotal | 4 |
| Appliances | Central Vacuum, Dishwasher, Dryer, Garburator, Microwave, Refrigerator, Washer, Range - Gas, Hood Fan, Window Coverings, Garage Door Opener |
| ArchitecturalStyle | 2 Level |
| BasementDevelopment | Finished |
| BasementType | Full (finished) |
| ConstructedDate | 2010 |
| ConstructionMaterial | Wood Frame |
| ConstructionStyleAttachment | Detached |
| CoolingType | Central Air Conditioning |
| ExteriorFinish | Wood |
| FireplacePresent | Yes |
| FireplaceTotal | 1 |
| FoundationType | Poured Concrete |
| HalfBathTotal | 1 |
| HeatingFuel | Natural Gas |
| HeatingType | Forced Air |
| StoriesTotal | 2 |
| SizeInterior | 3198 Sqft |
| Type | House |
| UtilityWater | Municipal Water |
Parking
| Detached Garage |
Land
| Acreage | No |
| FenceType | Fence |
| LandAmenities | Park, Shopping |
| Sewer | Municipal Sewage System |
| SizeDepth | 104 Ft |
| SizeFrontage | 40 Ft |
| SizeTotalText | Under 1/2 Acre |
| ZoningDescription | Rl8 Sp:129 |
Rooms
| Level | Type | Length | Width | Dimensions |
|---|---|---|---|---|
| Second Level | 4pc Bathroom | 8'1'' x 5'0'' | ||
| Second Level | Bedroom | 17'2'' x 12'7'' | ||
| Second Level | 3pc Bathroom | 6'0'' x 6'11'' | ||
| Second Level | Bedroom | 14'4'' x 10'8'' | ||
| Second Level | 4pc Bathroom | 8'3'' x 9'3'' | ||
| Second Level | Primary Bedroom | 13'1'' x 15'7'' | ||
| Lower Level | Laundry Room | 8'7'' x 10'0'' | ||
| Lower Level | 3pc Bathroom | 4'9'' x 10'2'' | ||
| Lower Level | Bedroom | 20'9'' x 14'6'' | ||
| Lower Level | Recreation Room | 17'2'' x 18'8'' | ||
| Main Level | Office | 12'9'' x 14'9'' | ||
| Main Level | 2pc Bathroom | 3'8'' x 4'10'' | ||
| Main Level | Kitchen | 17'10'' x 12'11'' | ||
| Main Level | Dining Room | 16'1'' x 9'0'' | ||
| Main Level | Great Room | 16'1'' x 12'11'' |
https://www.realtor.ca/real-estate/29405441/44-head-street-oakville
Laurie Blaha
Salesperson
1235 North Service Rd. W. #2
Oakville, Ontario L6M 2W2
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February 27 2026 02:18:23
REALTORS® Association of Hamilton-Burlington
RE/MAX Aboutowne Realty Corp.