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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.
| Room | Level | Size |
|---|---|---|
| Laundry room | Lower level | 10'0'' x 8'7'' |
| 3pc Bathroom | Lower level | 10'2'' x 4'9'' |
| Bedroom | Lower level | 14'6'' x 20'9'' |
| Recreation room | Lower level | 18'8'' x 17'2'' |
| 4pc Bathroom | Second level | 5'0'' x 8'1'' |
| Bedroom | Second level | 12'7'' x 17'2'' |
| 3pc Bathroom | Second level | 6'11'' x 6'0'' |
| Bedroom | Second level | 10'8'' x 14'4'' |
| 4pc Bathroom | Second level | 9'3'' x 8'3'' |
| Primary Bedroom | Second level | 15'7'' x 13'1'' |
| Office | Main level | 14'9'' x 12'9'' |
| 2pc Bathroom | Main level | 4'10'' x 3'8'' |
| Kitchen | Main level | 12'11'' x 17'10'' |
| Dining room | Main level | 9'0'' x 16'1'' |
| Great room | Main level | 12'11'' x 16'1'' |