44 Head Street, Oakville, ON

Oakville, 1002 - CO Central Hood
Wilson and Rebecca
3+1 Br | 5 Bath | 2000-2500 Sqft
$2,299,000 For Sale

Property Overview

  • Detached — 2-Storey
  • SqFt: | 2000-2500 Sqft
  • Lot Size: 40.00 x 104.33 Acres
  • Age: 6-15 Years
  • Basement: Full, Finished
  • Exterior: Wood
  • Taxes: 9,999 / 2025
  • Zoning: n/a
  • MLS #: W13044812
  • Sewer: Sewer
  • Heat Source: Gas , Forced Air

Property Description

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.

KitchenAid Fridge/freezer, KitchenAid Gas stove, KitchenAid dishwasher, Panasonic Microwave, Samsung washer & dryer, All light fixtures, All window coverings and blinds, TV bracket in Great Room, Central Vac and all attachments, Dyson Vacuum, Security system - ( not currently monitored)

Property Details

  • For: For Sale
  • Type: Detached
  • Style: 2-Storey
  • Lot: 40.00 x 104.33 Acres
  • Region: Halton
  • Hood: 1002 - CO Central
  • Zoning: n/a
  • Lot Irreg: Fronting on: South
  • Fronting On: South

Building Details

  • Age: 6-15 Years
  • Exterior: Wood
  • Heat: Gas , Forced Air
  • A/C: Central Air
  • Interior Features: Central Vacuum
  • Pool: None
  • Sewer: Sewer
  • Garage: Detached
  • Total Parking: 7.00

Property Interior

  • Sqft: 2000-2500 Sqft
  • Bed: 3 +1
  • Bath: 5
  • Kitchen: 1
  • Family Room: No
  • Basement: Full, Finished
Rooms Details

Great Room

Main Level

4.9 x 3.94

Fireplace, Hardwood Floor, Walk-Out

Dining Room

Main Level

4.9 x 2.74

Hardwood Floor, Walk-Out

Kitchen

Main Level

5.44 x 3.94

Hardwood Floor, Granite Counters, Centre Island

Office

Main Level

3.89 x 4.5

Hardwood Floor, French Doors

Bathroom

Main Level

1.12 x 1.47

2 Pc Bath

Primary Bedroom

Second Level

3.99 x 4.5

Walk-In Closet(s), 4 Pc Ensuite

Bathroom

Second Level

2.51 x 2.82

4 Pc Ensuite, Heated Floor, Soaking Tub

Bedroom 2

Second Level

4.37 x 3.25

Walk-In Closet(s), 3 Pc Ensuite

Bathroom

Second Level

1.83 x 2.11

3 Pc Ensuite, Heated Floor

Bedroom 3

Second Level

5.23 x 5.69

Walk-In Closet(s), 4 Pc Ensuite

Bathroom

Second Level

2.46 x 1.52

4 Pc Ensuite, Heated Floor

Recreation

Lower Level

5.23 x 4.42

Pot Lights

Bedroom 4

Lower Level

6.32 x 4.42

Bathroom

Lower Level

1.45 x 3.1

3 Pc Bath

Laundry

Lower Level

2.62 x 3.05

Property Listed by: RE/MAX ABOUTOWNE REALTY CORP.
Virtual Tour: https://tours.vogelcreative.ca/listing-preview/105995536

Home Valuation Estimate

What is 44 Head Street, Oakville, ON worth in today’s 1002 - CO Central, Oakville market?

This HomeZira valuation preview helps buyers and sellers think through the asking price for this 3-bedroom Detached with 2000-2500 sq. ft. in 1002 - CO Central, Oakville. The full estimate reviews the property’s location, home type, bedroom count, size range, age, and nearby comparable market activity after sign-in.

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Location

  • Address: 44 Head Street
  • Neighborhood: 1002 - CO Central
  • Zip/Postal Code: L6K 1L5
  • Nearby Amenities: Electric Car Charger, Fenced Yard, Public Transit
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About 44 Head Street, Oakville, ON L6K 1L5, Oakville

Located at 44 Head Street, Oakville, ON in Oakville (1002 - CO Central neighbourhood), near Wilson and Rebecca. This freehold home offers Detached, ["2-Storey"], 3 bedrooms, 5 bathrooms and 2000-2500 sq.ft. (approx.) in a layout suited to everyday family living. Basement: Full, Finished • 7 parking spots • Garage: Detached • Heating: Gas Forced Air • Cooling: Central Air. Property taxes are approximately $9,999 for 2025. 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.

FAQs for 44 Head Street, Oakville, ON , 1002 - CO Central , Oakville

What are the listing details for 44 Head Street, Oakville, ON?
44 Head Street, Oakville, ON is a Detached for sale in Oakville, in the 1002 - CO Central neighbourhood, Halton. The current list price is $2,299,000. MLS number: W13044812.
How many bedrooms and bathrooms does this home have?
44 Head Street, Oakville, ON is listed as a Detached with a ["2-Storey"] style, featuring 3+1 bedroom(s) and 5 bathroom(s). The listed interior size range is 2000-2500 sq. ft..
What lot, basement, garage, or parking details are listed?
The lot size is listed as approximately 40.00 x 104.33 Acres. The basement is listed as: Full, Finished. Garage type: Detached. Total parking: 7 space(s).
What heating, cooling, and exterior details are shown?
Heating is listed as: Gas, Forced Air. Cooling is listed as: Central Air. Exterior/construction materials are listed as: Wood .
Where is this property located?
44 Head Street, Oakville, ON is located in the 1002 - CO Central neighbourhood of Oakville. The listed cross street is Wilson and Rebecca.
What information is available on this public listing page?
The public listing page shows current active listing information, property photos, room details when available, map location, listed price, property features, and contact options. Annual taxes are listed as $9,999 / 2025. Valuation tools and similar sold-property previews are available after sign-in where applicable, without displaying sold data in this public FAQ.

FAQ content is based on current active listing fields shown on this page. Sold prices, sold comparables, and VOW-only details are not included in this public FAQ.