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44 Head Street — Photo 11 / 51

$2,299,000

44 Head Street

1002 - CO Central · Detached

4

Beds

5

Baths

2000-2500

Sqft

7

Parking

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

TypeDetached
Community1002 - CO Central
MunicipalityOakville
ListedFeb 27, 2026
StatusActive
MLS#W12826420

Inside

Bedrooms4
Bathrooms5

Building

Size2000-2500 sqft

Parking

Total Parking7

Room Sizes

Main Level

Great Room16.1' x 12.9'
Dining Room16.1' x 9.0'
Kitchen17.8' x 12.9'
Office12.8' x 14.8'
Bathroom3.7' x 4.8'

Upper Level

Primary Bedroom13.1' x 14.8'
Bathroom8.2' x 9.3'
Bedroom 214.3' x 10.7'
Bathroom6.0' x 6.9'
Bedroom 317.2' x 18.7'
Bathroom8.1' x 5.0'

Basement

Recreation17.2' x 14.5'
Bedroom 420.7' x 14.5'
Bathroom4.8' x 10.2'
Laundry8.6' x 10.0'

Sale History

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Area Stats

1002 - CO Central · Last 90 days

Sales

$1,035,000

Median Price

34

Avg DOM

34

Sold

Leases

$2,700

Median Rent

33

Avg DOM

41

Leased

Listed by RE/MAX ABOUTOWNE REALTY CORP.

Quick details

Price$2,299,000
TypeDetached
TransactionFor Sale
StatusActive
MLS#W12826420
Beds4
Baths5
Size2000-2500 sqft

Zoned Schools

Elementary

Secondary