44 Head Street, Oakville, ON

$2,299,000
MLS#:W13044812
4 beds
5 baths
2000-2500 sqft
7.0 parking
Residential Freehold
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Description

Property Highlights

Welcome to this remarkable ["2-Storey"] detached located in the coveted neighborhood of 1002 - CO Central. Expertly crafted featuring premium wood construction, this residence presents an exceptional opportunity offered at $2,299,000 to acquire a beautiful home in a highly sought-after setting. Designed for both comfortable daily living and elegant entertaining, the layout maximizes natural light, functional flow, and lifestyle utility.

  • 4 Bedrooms and 5 Bathrooms
  • Generous living space spanning 2000-2500 sqft on a premium 40 x 104.33 ft lot
  • Features a ["full", "finished"] basement, adding superb versatility for recreation, a home gym, or extra storage
  • 7.0 total parking spaces available with a convenient detached configuration
  • Notable attributes: Central Vacuum
  • equipped with ["central air"] central cooling and highly efficient forced air heating via gas

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, cafes & 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.

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Key Features

Bedrooms
4
Bathrooms
5
Kitchens
1
Living Area
2000-2500 sqft
Property Type
Residential Freehold

Additional Details

StatusActive
Listed Date4/24/2026
Transaction TypeFor Sale

Property Details

Property Sub-TypeDetached
ConstructionWood
Lot Size40 × 104.33 Acres
CountyHalton
Annual Tax$9,999
Legal DescriptionPT LT 7, BLK 95, PL 1, AS IN 526751. TOWN OF OAKVILLE

Parking & Garage

Parking Spaces7.0
Garage Spaces6
Garage TypeDetached

Heating & Cooling

Heat SourceGas
Heat TypeForced Air
Cooling["Central Air"]

Features

Property Features

Electric Car Charger, Fenced Yard, Public Transit

Community Features

Location

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44 Head Street, Oakville, ON

City & Neighborhood Guide

Comprehensive neighborhood overview, demographics, and school rankings for 1002 Co Central, Oakville.

Verified Local Data
Population6,202,225
Median Age41.2 Yrs
Ownership82% Owners
Avg Area List Price$850,000

People & Families

Age Distribution

Household Composition

One-person households
25%
Families with children
50%
Couples without children
24%
Other households
0%

Top Ethnic Origins

English22%
Canadian16%
Scottish16%
Irish15%

Local Schools Guide

Elementary Schools

Sunningdale
PublicOakville, Ontario, L6H 1T4
8.8
Abbey Lane
Public1160 Old Abbey Lane, Oakville, Ontario, L6M 1S4
7.5
Forest Trail
PublicForest Trail Place, Oakville, Ontario, L6M 2G3
10.0
Montclair
Public1285 Montclair Drive, Oakville, Ontario, L6H 1Z3
4.4
du Chêne
Public150 Ridge Drive, Oakville, Ontario, L6H 1B8
9.4

Secondary Schools

White Oaks
PublicOnslow Court, Oakville, Ontario, L6H 1H9
8.8
Gaétan Gervais
Public1075 McCraney Street East, Oakville, Ontario, L6H 1H9
9.3
St. Ignatius of Loyola
Catholic1550 Nottinghill Gate, Oakville, Ontario, L6M 1X7
8.1

Homes & Housing

Structural Home Types

Tenure (Ownership vs Rental)

Owner-Occupied82%
Rented18%

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Property History

No historical data available for this property.

This could be the first listing for this address.

Pricing & Value Insights

Data-driven valuation for 44 Head Street, Oakville, ON L6K 1L5

Estimated Sales Range
$1.2M - $1.4M

Based on 0 recent similar sales in the pocket.

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Properties in this area are selling at a steady pace.

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Financial Audit

Estimated Costs

Loan Amount$1,839,200
Monthly Mortgage$10,686
Property Tax (Est.)$833
Utilities & Maint.$350
Total Monthly Cost$11,869

Nearby School Rankings

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Within 2km radiusFraser Institute Ratings

Nearby Listings

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Notice: Market Insights are generated by analyzing real-time data and should be used for informational purposes only. Consult with a licensed professional for exact valuations.

Disclaimer: AI Insights are generated by an automated system and should be used for informational purposes only. While we strive for accuracy using current market data and deep-learning models, these assessments do not constitute professional real estate, legal, or financial advice. All property values, predictions, and scores are estimates. We strongly recommend verifying all property details and conducting independent due diligence with a licensed professional before making any purchase decisions.