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44 Head Street — Detached

Sold

Oakville, ON L6K 1L5

4 Bed · 5 Bath · Detached

MLS #W13044812

$2,100,000

Sold on September 14, 2026

September 14, 2026

Originally listed at $2,299,000 64 days on market

About This Property

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.

Property Details

Bedrooms

4

Bathrooms

5

Square Feet

2000-2500 sqft

Property Type

Detached

Style2-Storey
Approx. Age6-15 years
Lot Size40 104 ft
Frontage40.0 ft
Depth104.3 ft
GarageDetached
BasementFull, Finished
CoolingCentral Air
HeatingForced Air
FireplaceYes
Parking Spaces7
Listed OnApr 23, 2026
MLS Size2000-2500
Property Tax$9,999/year

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Rooms

NameSize (m)Size (ft)Features
Great Room(Main)4.9 x 3.9416.1 x 12.9-
Great Room(Main)4.9 x 3.9416.1 x 12.9-
Great Room(Main)4.9 x 3.9416.1 x 12.9-
Great Room(Main)4.9 x 3.9416.1 x 12.9-
Great Room(Main)4.9 x 3.9416.1 x 12.9-
Great Room(Main)4.9 x 3.9416.1 x 12.9-
Great Room(Main)4.9 x 3.9416.1 x 12.9-
Great Room(Main)4.9 x 3.9416.1 x 12.9-
Dining Room(Main)4.9 x 2.7416.1 x 9.0-
Dining Room(Main)4.9 x 2.7416.1 x 9.0-
Dining Room(Main)4.9 x 2.7416.1 x 9.0-
Dining Room(Main)4.9 x 2.7416.1 x 9.0-
Dining Room(Main)4.9 x 2.7416.1 x 9.0-
Dining Room(Main)4.9 x 2.7416.1 x 9.0-
Dining Room(Main)4.9 x 2.7416.1 x 9.0-
Dining Room(Main)4.9 x 2.7416.1 x 9.0-
Kitchen(Main)5.44 x 3.9417.8 x 12.9-
Kitchen(Main)5.44 x 3.9417.8 x 12.9-
Kitchen(Main)5.44 x 3.9417.8 x 12.9-
Kitchen(Main)5.44 x 3.9417.8 x 12.9-
Kitchen(Main)5.44 x 3.9417.8 x 12.9-
Kitchen(Main)5.44 x 3.9417.8 x 12.9-
Kitchen(Main)5.44 x 3.9417.8 x 12.9-
Kitchen(Main)5.44 x 3.9417.8 x 12.9-
Office(Main)3.89 x 4.512.8 x 14.8-
Office(Main)3.89 x 4.512.8 x 14.8-
Office(Main)3.89 x 4.512.8 x 14.8-
Office(Main)3.89 x 4.512.8 x 14.8-
Office(Main)3.89 x 4.512.8 x 14.8-
Office(Main)3.89 x 4.512.8 x 14.8-
Office(Main)3.89 x 4.512.8 x 14.8-
Office(Main)3.89 x 4.512.8 x 14.8-
Bathroom(Main)1.12 x 1.473.7 x 4.8-
Bathroom(Main)1.12 x 1.473.7 x 4.8-
Bathroom(Main)1.12 x 1.473.7 x 4.8-
Bathroom(Main)1.12 x 1.473.7 x 4.8-
Bathroom(Main)1.12 x 1.473.7 x 4.8-
Bathroom(Main)1.12 x 1.473.7 x 4.8-
Bathroom(Main)1.12 x 1.473.7 x 4.8-
Bathroom(Main)1.12 x 1.473.7 x 4.8-
Primary Bedroom(Second)3.99 x 4.513.1 x 14.8-
Primary Bedroom(Second)3.99 x 4.513.1 x 14.8-
Primary Bedroom(Second)3.99 x 4.513.1 x 14.8-
Primary Bedroom(Second)3.99 x 4.513.1 x 14.8-
Primary Bedroom(Second)3.99 x 4.513.1 x 14.8-
Primary Bedroom(Second)3.99 x 4.513.1 x 14.8-
Primary Bedroom(Second)3.99 x 4.513.1 x 14.8-
Primary Bedroom(Second)3.99 x 4.513.1 x 14.8-
Bathroom(Second)2.51 x 2.828.2 x 9.3-
Bathroom(Second)2.51 x 2.828.2 x 9.3-
Bathroom(Second)2.51 x 2.828.2 x 9.3-
Bathroom(Second)2.51 x 2.828.2 x 9.3-
Bathroom(Second)2.51 x 2.828.2 x 9.3-
Bathroom(Second)2.51 x 2.828.2 x 9.3-
Bathroom(Second)2.51 x 2.828.2 x 9.3-
Bathroom(Second)2.51 x 2.828.2 x 9.3-
Bedroom 2(Second)4.37 x 3.2514.3 x 10.7-
Bedroom 2(Second)4.37 x 3.2514.3 x 10.7-
Bedroom 2(Second)4.37 x 3.2514.3 x 10.7-
Bedroom 2(Second)4.37 x 3.2514.3 x 10.7-
Bedroom 2(Second)4.37 x 3.2514.3 x 10.7-
Bedroom 2(Second)4.37 x 3.2514.3 x 10.7-
Bedroom 2(Second)4.37 x 3.2514.3 x 10.7-
Bedroom 2(Second)4.37 x 3.2514.3 x 10.7-
Bathroom(Second)1.83 x 2.116.0 x 6.9-
Bathroom(Second)1.83 x 2.116.0 x 6.9-
Bathroom(Second)1.83 x 2.116.0 x 6.9-
Bathroom(Second)1.83 x 2.116.0 x 6.9-
Bathroom(Second)1.83 x 2.116.0 x 6.9-
Bathroom(Second)1.83 x 2.116.0 x 6.9-
Bathroom(Second)1.83 x 2.116.0 x 6.9-
Bathroom(Second)1.83 x 2.116.0 x 6.9-
Bedroom 3(Second)5.23 x 5.6917.2 x 18.7-
Bedroom 3(Second)5.23 x 5.6917.2 x 18.7-
Bedroom 3(Second)5.23 x 5.6917.2 x 18.7-
Bedroom 3(Second)5.23 x 5.6917.2 x 18.7-
Bedroom 3(Second)5.23 x 5.6917.2 x 18.7-
Bedroom 3(Second)5.23 x 5.6917.2 x 18.7-
Bedroom 3(Second)5.23 x 5.6917.2 x 18.7-
Bedroom 3(Second)5.23 x 5.6917.2 x 18.7-
Bathroom(Second)2.46 x 1.528.1 x 5.0-
Bathroom(Second)2.46 x 1.528.1 x 5.0-
Bathroom(Second)2.46 x 1.528.1 x 5.0-
Bathroom(Second)2.46 x 1.528.1 x 5.0-
Bathroom(Second)2.46 x 1.528.1 x 5.0-
Bathroom(Second)2.46 x 1.528.1 x 5.0-
Bathroom(Second)2.46 x 1.528.1 x 5.0-
Bathroom(Second)2.46 x 1.528.1 x 5.0-
Recreation(Lower)5.23 x 4.4217.2 x 14.5-
Recreation(Lower)5.23 x 4.4217.2 x 14.5-
Recreation(Lower)5.23 x 4.4217.2 x 14.5-
Recreation(Lower)5.23 x 4.4217.2 x 14.5-
Recreation(Lower)5.23 x 4.4217.2 x 14.5-
Recreation(Lower)5.23 x 4.4217.2 x 14.5-
Recreation(Lower)5.23 x 4.4217.2 x 14.5-
Recreation(Lower)5.23 x 4.4217.2 x 14.5-
Bedroom 4(Lower)6.32 x 4.4220.7 x 14.5-
Bedroom 4(Lower)6.32 x 4.4220.7 x 14.5-
Bedroom 4(Lower)6.32 x 4.4220.7 x 14.5-
Bedroom 4(Lower)6.32 x 4.4220.7 x 14.5-
Bedroom 4(Lower)6.32 x 4.4220.7 x 14.5-
Bedroom 4(Lower)6.32 x 4.4220.7 x 14.5-
Bedroom 4(Lower)6.32 x 4.4220.7 x 14.5-
Bedroom 4(Lower)6.32 x 4.4220.7 x 14.5-
Bathroom(Lower)1.45 x 3.14.8 x 10.2-
Bathroom(Lower)1.45 x 3.14.8 x 10.2-
Bathroom(Lower)1.45 x 3.14.8 x 10.2-
Bathroom(Lower)1.45 x 3.14.8 x 10.2-
Bathroom(Lower)1.45 x 3.14.8 x 10.2-
Bathroom(Lower)1.45 x 3.14.8 x 10.2-
Bathroom(Lower)1.45 x 3.14.8 x 10.2-
Bathroom(Lower)1.45 x 3.14.8 x 10.2-
Laundry(Lower)2.62 x 3.058.6 x 10.0-
Laundry(Lower)2.62 x 3.058.6 x 10.0-
Laundry(Lower)2.62 x 3.058.6 x 10.0-
Laundry(Lower)2.62 x 3.058.6 x 10.0-
Laundry(Lower)2.62 x 3.058.6 x 10.0-
Laundry(Lower)2.62 x 3.058.6 x 10.0-
Laundry(Lower)2.62 x 3.058.6 x 10.0-
Laundry(Lower)2.62 x 3.058.6 x 10.0-

Room Dimensions Available

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44 Head Street History

Complete transaction history for this property

Terminated

Listed: Feb 25, 2026

$229,900,000

1 days on marketSale
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3 More Transactions Available

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Transaction History Available

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Price History

Original List Price

$2,299,000

Listed on Apr 23, 2026

Sold Price

$2,100,000

Sold on Sep 14, 2026

-$199,000

-8.7%

64 days on market

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OVAIS QASSIM

Broker of Record

PREMIER MATRIX REALTY LTD. BROKERAGE

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Home Features

Property TypeDetached
Style2-Storey
Approx. Age6-15 years
Lot Size40 × 104 ft
Frontage40.0 ft
Depth104.3 ft
GarageDetached
BasementFull, Finished
CoolingCentral Air
FireplaceYes

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About 44 Head Street, Oakville, ON L6K 1L5

44 Head Street, Oakville, ON L6K 1L5 is a 4-bedroom, 5-bathroom 2-storey detached with approximately 2000-2500 square feet of living space, situated on a 40 104 foot lot. This property is currently sold (sold for $2,100,000). The home features a detached garage and a full, finished basement, built approximately 6-15 years ago.

1002 - CO Central Neighbourhood

This home is located in 1002 - CO Central, part of Oakville in the Halton area. Explore more homes for sale and recently sold properties in this neighbourhood.

Whether you are looking to buy, sell, or lease in 1002 - CO Central, our team of experienced real estate professionals can help you navigate the market and find the perfect home. Contact us today for a free consultation.

44 Head Street, Oakville, ON L6K 1L5

44 Head Street, Oakville, ON L6K 1L5 sold,4 bedroom detached 1002 - CO Central,Oakville homes for sale,Halton real estate,2-Storey homes, detached sold