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Listing Brokerage: RE/MAX ABOUTOWNE REALTY CORP.Last Updated: Apr 25, 2026 at 12:46 PM EDTData provided by the Toronto Regional Real Estate Board (TRREB) via PropTx / AMPRE.
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44 Head Street, Oakville, ON L6K 1L5, Oakville, ON, L6K 1L5

MLS: W13044812 | Detached

$2,299,000

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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.

Directions: Rebecca to Wilson to Head St
Inclusions: 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)

Quick Facts

  • Property Type: Detached
  • Style: 2-Storey
  • Bedrooms: 4 (3 above, 1 below)
  • Bathrooms: 5
  • Fireplaces: 1
  • Parking: 7.0 spaces
  • Lot Size: 0.1000 acres (0.04 ha)

Costs

  • Annual Taxes: $9,999.00 (2025)

Listing Provided by: RE/MAX ABOUTOWNE REALTY CORP.
Board: Toronto Regional Real Estate Board
Data provided via CREA DDF®.

Detailed Features

Interior & Systems

  • Cooling: Central Air
  • Basement: Full, Finished
  • Fireplace Features: Natural Gas

Exterior & Construction

  • Style: 2-Storey
  • Exterior: Porch, Patio
  • Roof: Asphalt Shingle
  • Construction: Wood
  • Foundation: Poured Concrete
  • Sewer: Sewer

Lot & Land

  • Lot Size: 0.1000 acres (0.04 ha)
  • Pool: None
  • Zoning: RL8 sp:129

Community & Neighbourhood

  • Neighbourhood: 1002 - CO Central

Listing Information

MLS® NumberW13044812
BoardToronto Regional Real Estate Board
Originating SystemToronto Regional Real Estate Board
BrokerageRE/MAX ABOUTOWNE REALTY CORP.
Date ListedApril 25, 2026
Last UpdatedApril 25, 2026

Listing History

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Location & Neighborhood

📍44 Head Street, Oakville, ON L6K 1L5, Oakville, ON, L6K 1L5

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Cathy Dou
Cathy Dou
Broker of Record
[email protected]647-691-6364
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44 Head Street, Oakville, ON L6K 1L5, Oakville, ON, L6K 1L5

ASAP
 
TUE
5
May
WED
6
May
THU
7
May
FRI
8
May
SAT
9
May
SUN
10
May
MON
11
May
MorningAfternoonEvening
Cathy Dou
Cathy Dou
Broker of Record
[email protected]647-691-6364
Ask a Question