$2,299,000

44 Head Street, Oakville, ON L6K 1L5

1002 - CO Central, Oakville,

| | | 2,500 sq.ft. | Year Built: 6-15 |

Properties with this icon are courtesy of TRREB.

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 Info
MLS®: W12826420
Listing Courtesy of RE/MAX ABOUTOWNE REALTY CORP.
Total Bedrooms 4
Total Bathrooms 5
Basement 1
Floor Space 2000-2500 sq.ft.
Lot Size 4173 sq.ft.
Style 2-Storey
Last Updated 2026-02-27
Property Type House
Listed Price $2,299,000
Unit Pricing $920/sq.ft.
Tax Estimate $9,999/Year
Year Built 6-15
Rooms
More Details
Exterior Finish Wood
Parking Cover 1
Parking Total 6
Water Supply Municipal
Foundation Sewer
Summary
    Location and General Information
  • HoldoverDays: 90
  • Architectural Style: 2-Storey
  • Property Type: Residential Freehold
  • Property Sub Type: Detached
  • DirectionFaces: South
  • GarageType: Detached
  • Directions: Rebecca to Wilson to Head St
  • Taxes and HOA Information
  • Tax Year: 2025
  • Parking
  • ParkingSpaces: 6
  • Parking Total: 7
Interior and Exterior Features
    Bathrooms Information
  • WashroomsType1: 1
  • WashroomsType1Level: Main
  • WashroomsType2: 1
  • WashroomsType2Level: Second
  • WashroomsType3: 1
  • WashroomsType3Level: Second
  • WashroomsType4: 1
  • WashroomsType4Level: Second
  • WashroomsType5: 1
  • WashroomsType5Level: Basement
  • Bedrooms Information
  • BedroomsAboveGrade: 3
  • BedroomsBelowGrade: 1
  • Interior Features
  • Fireplaces Total: 1
  • Interior Features: Central Vacuum
  • Basement: Full, Finished
  • Cooling: Central Air
  • HeatSource: Gas
  • HeatType: Forced Air
  • LaundryLevel: Lower Level
  • Exterior Features
  • ConstructionMaterials: Wood
  • Exterior Features: Porch, Patio
  • Roof: Asphalt Shingle
  • Pool Features: None
Property
    Utilities
  • Sewer: Sewer
  • Property and Assessments
  • Foundation Details: Poured Concrete
  • Lot Information
  • Parcel Number: 248190071
  • LotSizeUnits: Acres
  • LotDepth: 104.33
  • LotWidth: 40
  • Others
  • PropertyFeatures: Electric Car Charger, Fenced Yard, Public Transit
Sold History
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