About 44 Head Street
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 4th bedroom, 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.
Features of 44 Head Street
| MLS® # | 40764298 |
|---|---|
| Price | $2,399,000 |
| Bedrooms | 4 |
| Bathrooms | 5.00 |
| Full Baths | 4 |
| Half Baths | 1 |
| Square Footage | 2,183 |
| Acres | 0.00 |
| Year Built | 2010 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Style | Two Story |
| Status | Active |
Community Information
| Address | 44 Head Street |
|---|---|
| Area | 1 - Oakville |
| Subdivision | 1002 - CO Central |
| City | Oakville |
| County | Halton |
| Province | ON |
| Postal Code | L6K 1L5 |
Amenities
| Parking Spaces | 6 |
|---|---|
| Parking | Detached Garage, Garage Door Opener, Asphalt |
| # of Garages | 1.00 |
| Is Waterfront | No |
| Waterfront | River/Stream |
Interior
| Interior Features | Central Vacuum, Auto Garage Door Remote(s), Built-In Appliances |
|---|---|
| Appliances | Garborator, Dishwasher, Dryer, Gas Oven/Range, Microwave, Range Hood, Refrigerator, Washer |
| Heating | Forced Air, Natural Gas |
| Cooling | Central Air |
| Fireplace | Yes |
| # of Fireplaces | 1 |
| Has Basement | Yes |
| Basement | Full, Finished, Sump Pump |
Exterior
| Exterior Features | Landscaped |
|---|---|
| Lot Description | Urban, Rectangular, Ample Parking, Park, Quiet Area, Shopping Nearby |
| Windows | Window Coverings |
| Roof | Asphalt Shing |
| Construction | Wood Siding |
| Foundation | Poured Concrete |
Additional Information
| Date Last Updated | October 16th, 2025 |
|---|---|
| Zoning | RL8 sp:129 |
Listing Details
| Office | RE/MAX Aboutowne Realty Corp. |
|---|