$2,299,000
FOR SALE

Detached 2-Storey

Bedrooms: 4Bathrooms: 5Lot: 40 x 104.33 acres
2025 Taxes: $9,999

44 Head St
Oakville, ON L6K 1L5 | 1002 - CO Central | Halton

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, cafes & 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.
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Listed By RE/MAX ABOUTOWNE REALTY CORP.
Data Provided By Toronto Regional Real Estate Board
MLS® Listing Number W13044812
Last Updated Apr 25, 2026
Property Summary
Property Type Detached

More like this:
PIN 248190071
Legal Description PT LT 7, BLK 95, PL 1, AS IN 526751. TOWN OF OAKVILLE
Possession Date Flexible
Taxes (2025) $9,999
Directions/Cross Streets Wilson and Rebecca
Neighbourhood 1002 - CO Central
Area Halton
Price History

Interested in obtaining the full price history for this property?
Contact us!Contact us! Our real estate professionals would be happy to provide a complete listing history with historical sold prices and dates.

Detailed Information
Fronting On South
Special Designations Unknown
Bedrooms 4
Bathrooms 5
Lot 40 x 104.33 acres
Exterior Wood
Air Conditioning Central Air
Family Room Y
Fireplace/Stove Y
Basement Full, Finished
Garage Type Detached
Garage/Park Spaces Y
Parking Spaces 6
Heat Source Gas
Heat Type Forced Air
Sewers Sewer

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