44 Head Street
Description
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.
Property Details
Rooms
Great Room Main
Dining Room Main
Kitchen Main
Office Main
Bathroom Main
Primary Bedroom Second
Bathroom Second
Bedroom 2 Second
Bathroom Second
Bedroom 3 Second
Bathroom Second
Recreation Lower
Characteristics
Property
Inside
Building
Parking
Fees
Land
Sale History
| Date | Event | Price | MLS Number |
|---|---|---|---|
| Feb 27, 2026 | Listed | $2,299,000 | W12826420 |
| Feb 27, 2026 | Removed | W12826082 | |
| Feb 27, 2026 | Listed | $229,900,000 | W12826082 |
| Feb 27, 2026 | Removed | W12379865 | |
| Sep 4, 2025 | Listed | $2,299,000 | W12379865 |
| Sep 4, 2025 | Removed | W12246254 | |
| Jun 26, 2025 | Listed | $2,599,000 | W12246254 |
| Dec 14, 2012 | Sold | $1,047,500 | W2480449 |
| Oct 4, 2012 | Listed | $1,169,000 | W2480449 |
| Oct 3, 2012 | Removed | W2417757 | |
| Jul 13, 2012 | Listed | $1,189,000 | W2417757 |
| Jul 18, 2012 | Removed | O2341706 | |
| Apr 19, 2012 | Listed | $1,249,000 | O2341706 |
| Jul 11, 2012 | Removed | W2342192 | |
| Apr 20, 2012 | Listed | $1,249,000 | W2342192 |
| Apr 18, 2012 | Removed | W2268532 | |
| Jan 18, 2012 | Listed | $1,249,000 | W2268532 |
| Jan 16, 2012 | Removed | W2205221 | |
| Sep 24, 2011 | Listed | $1,249,000 | W2205221 |
| Oct 27, 2009 | Sold | $419,000 | O1711948 |
| Sep 25, 2009 | Listed | $439,900 | O1711948 |
| Jun 29, 2009 | Removed | O1563554 | |
| Feb 20, 2009 | Listed | $424,900 | O1563554 |
| Oct 24, 2008 | Removed | O1442755 | |
| Aug 9, 2008 | Listed | $473,900 | O1442755 |
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