Jolanda
Learie
Natasha
44 Head Street - $2,299,000
44 Head Street - $2,299,000
44 Head Street
$2,299,000
Oakville, OntarioL6K1L5
4 beds
5 baths
7 parking
MLS#: 40823865Listed: about 1 month agoUpdated:1 day ago
Description
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:63050)Details
Details for 44 Head Street, Oakville, Ontario- Property Type
- Single Family
- Building Type
- House
- Storeys
- 2
- Neighborhood
- 1002 - CO Central
- Land Size
- -
- Year Built
- 2010
- Annual Property Taxes
- $9,999
- Parking Type
- Detached Garage
Inside
- Appliances
- Washer, Refrigerator, Central Vacuum, Range - Gas, Dishwasher, Dryer, Microwave, Garburator, Hood Fan, Window Coverings, Garage door opener
- Rooms
- 15
- Bedrooms
- 4
- Bathrooms
- 5
- Fireplace
- -
- Fireplace Total
- 1
- Basement
- Finished, Full
Building
- Architecture Style
- 2 Level
- Direction
- Rebecca north on Wilson to Head St
- Type of Dwelling
- house
- Roof
- -
- Exterior
- Wood
- Foundation
- Poured Concrete
- Flooring
- -
Land
- Sewer
- Municipal sewage system
- Lot Size
- -
- Zoning
- -
- Zoning Description
- RL8 sp:129
Parking
- Features
- Detached Garage
- Total Parking
- 7
Utilities
- Cooling
- Central air conditioning
- Heating
- Forced air, Natural gas
- Water
- Municipal water
Feature Highlights
- Community
- Quiet Area
- Lot Features
- Paved driveway, Sump Pump, Automatic Garage Door Opener
- Security
- -
- Pool
- -
- Waterfront
- -
Rooms
Rooms for 44 Head Street, Oakville, OntarioMap
Listatto.comCopyright 2026