44 HEAD Street, Oakville, Ontario, L6K1L5

Property 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:64974)

Quick Facts

• Property Type: House (Freehold)
• Style: 2 Level
• Bedrooms: 4 (3 above, 1 below)
• Bathrooms: 5 (1 half)
• Living Area: 3,198 sq ft (297.1 m²)
• Above Grade: 2,183 sq ft (202.8 m²)
• Below Grade: 1,015 sq ft (94.3 m²)
• Year Built: 2010
• Ownership: Freehold
• Attached: No
• Fireplaces: 1
• Parking: 7 spaces (Detached Garage)
• Frontage: 40 ft (12.2 m)

Costs

• Annual Taxes: $9,999.00

Listing Provided by: RE/MAX Aboutowne Realty Corp.
Board: Cornerstone Association of REALTORS®
Data provided via CREA DDF®.