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$2,299,000
Ontario,Oakville
For Sale Active
44 HEAD Street, Oakville, Ontario L6K1L5
  • 4
  • 5
  • 3,198 Sqft
Basic Details
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:62650)

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Basic Details
  • Property Type: Residential
  • Listing Type: For Sale
  • Listing ID: 40808082
  • Price: $2,299,000
  • Bedrooms: 4
  • Bathrooms: 5
  • Half Bathrooms: 1
  • Square Footage: 3,198 Sqft
  • Year Built: 2010
  • Status: Active
  • Property Sub Type: Single Family
  • Office Key: 294000
Features & Appliances
Features
  • Heating System: Forced air, Natural gas
  • Cooling System: Central air conditioning
  • Basement: Finished, Full
  • Fence: Fence
  • Parking: Detached Garage
  • Architectural Style: 2 Level
  • Exterior Features: Wood
  • Sewer: Municipal sewage system
  • Fireplaces Total: 1
Address Map
  • Location: CA, Ontario, Oakville, 1002 - CO Central, L6K1L5
  • Street: HEAD
  • Street Number: 44
  • Street Suffix: Street
  • Longitude: W80° 19' 28.1''
  • Latitude: N43° 26' 32.1''
Additional Information
  • Water Source:
  • Community Features:
  • Construction Materials:
  • Foundation Details:
  • Lot Features:
  • Stories: 2.0
Financial
  • Tax Annual Amount: 9999
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Listing updated: 2026-04-24 04:23:04
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Listing Information
  • List Agent Key: 2236132
  • List Office Key: 294000
  • Modification Timestamp: 2026-04-11T20:31:01Z
  • Originating System Name: Cornerstone Association of REALTORS®
  • Status Change Timestamp: 2026-04-11T20:23:38Z
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Listing updated: 2026-04-24 04:23:04
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