Re-listed 43 days ago

44 Head St, Oakville, Ontario L6K 1L5

Detached
3 + 1
5
~2000-2500 sqft
$•••,•••
$2,299,000
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Detached
3 + 1
5
~2000-2500 sqft

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Highlights

Property Estimate

Days on market43 days

Total days on market
290 days

Estimated valueNot available

Price/Sqft$1,034/sqft

Monthly cost

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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, 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 Details

Style2-Storey
View-
Age of property6-15
SqFt~2000-2500 SqFt
Lot Size4,173 Ac(104.33 x 40)
Parking Spaces7
MLS ®NumberW12826420
Community NameOld Oakville
Data SourceTRREB
Listing byRE/MAX ABOUTOWNE REALTY CORP.

Features

Heating: Forced Air
Central Vacuum
Cooling: Central Air
Fireplace
Basement: Full, Finished

Main Floor

Great Rm

4.9 x 3.94

Fireplace / hardwood floor / Walk-Out

Dining

4.9 x 2.74

hardwood floor / Walk-Out

Kitchen

5.44 x 3.94

hardwood floor / Granite Counter / Centre Island

Office

3.89 x 4.5

hardwood floor / French Doors


Features

Lot size: 4,173 Ac

Parking

Garage spaces 1

Garage type Detached

Other parking spaces 6

Total parking spaces 7


Property History

Feb 27, 2026
ListedActive
$2,299,000
43 days on market
history photo preview49
Listing by trreb®
Property listed by RE/MAX ABOUTOWNE REALTY CORP., Brokerage
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Market Data - Old Oakville

Geo Zone Map ThumbnailOld Oakville

Balanced Market

View Market Data

Detached house - for the past 30 days

Buyer's market Seller's market

Avg. Days on Market

Past 30 days

39 days

Compared to

2025

45 days

2024

12 days

2023

24 days

New Listings

Past 30 days

23 listings

Compared to

2025

26 listings

2024

20 listings

2023

22 listings

Units sold

Past 30 days

12 units

Compared to

2025

7 units

2024

9 units

2023

15 units

Median Sold Price

Past 30 days

$1,912,500

Compared to

2025

$2,200,000

2024

$1,350,000

2023

$2,495,000


Population and Demographics

Overview

Total population 12340
Average household income $232,063

Age (%)

0 to 19
17%
20 to 34
17%
35 to 49
17%
50 to 64
22%
65 and plus
26%

Household composition (%)

Single family
57%
Single person
39%
Multi person
4%
Multi family
0%

Mother tongue (%)

English
80%
Portuguese
2%
Arabic
2%
Mandarin
2%
Others
2%
Tagalog (Pilipino, Filipino)
2%
Spanish
2%
French
2%
Polish
1%
Italian
1%

House tenancy (%)

Renters
52%
Owners
48%

What’s nearby?Essentials within 5 km

Local Logic

Transportation Scores

Estimated Budget