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Home ON Greater Toronto Area Oakville Central Oakville
44 HEAD STREET
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44 HEAD STREET $2,599,000
$2,599,000
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44 HEAD STREET
Oakville (CO Central), Ontario L6K1L5

MLS® Number: W12246254
3 + 1
Bedrooms
5
Bathrooms
2000 - 2500
Square Feet

Listing 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 entertainers 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 4th bedroom, 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. (40769423)

Location Description

Rebecca and Chisholm

Property Summary

Property Type
Single Family
Building Type
House
Storeys
2
Square Footage
2000 - 2500 sqft
Community Name
1002 - CO Central
Title
Freehold
Land Size
40 x 104.3 FT
Age Of Building
6 to 15 years
Annual Property Taxes
$9,999
Parking Type
Detached Garage, Garage
Time on REALTOR.ca
38 days

Building

Bedrooms
Above Grade
3
Below Grade
1
Bathrooms
Total
5
Partial
1
Interior Features
Appliances Included
Garage door opener remote(s), Central Vacuum, Garburator, All, Blinds, Garage door opener, Alarm System, Window Coverings
Flooring
Hardwood
Basement Type
Full (Finished)
Building Features
Features
Level lot, Sump Pump
Foundation Type
Poured Concrete
Style
Detached
Construction Status
Insulation upgraded
Building Amenities
Fireplace(s)
Rental Equipment
Water Heater
Structures
Patio(s), Porch
Heating & Cooling
Cooling
Central air conditioning
Fireplace
1
Heating Type
Forced air (Natural gas)
Utilities
Utility Sewer
Sanitary sewer
Water
Municipal water
Exterior Features
Exterior Finish
Wood
Parking
Parking Type
Detached Garage, Garage
Total Parking Spaces
7

Measurements

Square Footage
2000 - 2500 sqft

Rooms

MetricImperial
Main level
Great room
Dining room
Kitchen
Office
Bathroom
Second level
Bathroom
Primary Bedroom
Bathroom
Bedroom 2
Bathroom
Bedroom 3
Lower level
Recreational, Games room
Bedroom 4
Bathroom
Laundry room

Land

Lot Features
Frontage
40 ft
Land Depth
104 ft ,3 in
Other Property Information
Zoning Description
RL8 sp 129
Data provided by: Toronto Regional Real Estate Board 1400 Don Mills Road, Toronto, Ontario M3B 3N1

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