44 Head Street, Oakville, ON L6K 1L5
See all 50 photos
44 Head Street, Oakville, ON L6K 1L5
44 Head Street, Oakville, ON L6K 1L5
44 Head Street, Oakville, ON L6K 1L5
44 Head Street, Oakville, ON L6K 1L5
REQUEST A TOUR If you would like to see this home without being there in person, select the "Virtual Tour" option and your agent will contact you to discuss available opportunities.
In-PersonVirtual Tour
Casora Realty

Casora Realty

+1(905) 332-4111
Listed by Laurie Blaha • RE/MAX Aboutowne Realty Corp.
$ 2,299,000
Est. payment /mo
Save Virtual Tour
Open Sat 2PM-4PM

44 Head Street Oakville, ON L6K 1L5

4 Beds

5 Baths

2,183 SqFt

Open House

Sat May 02, 2:00pm - 4:00pm

UPDATED:

Key Details

Property Type Single Family Home

Sub Type Detached

Listing Status Active

Purchase Type For Sale

Square Footage 2,183 sqft

Price per Sqft $1,053

MLS Listing ID 40823865

Style Two Story

Bedrooms 4

Full Baths 4

Half Baths 1

Abv Grd Liv Area 3,198

Year Built 2010

Annual Tax Amount $9,999

Property Sub-Type Detached

Source Cornerstone

Property Description

Welcome to 44 Head St—an exceptional residence in the heart of Oakville—just steps to Kerr Village, downtown boutiques, cafés & the lakefront. Here, vibrant walkability meets peaceful, tree-lined charm. Offering nearly 2,200 sq ft above grade + a fully finished 1,015 sq ft lower level, this timeless home blends character with modern comfort. Set behind manicured gardens, dark slate wood siding & crisp white trim frame a welcoming front porch—perfect for morning coffee or evening wine. Inside, 9' ceilings, hardwood floors, crown moulding & high baseboards create an elevated aesthetic. The entertainer's kitchen features granite countertops, a generous island, professional-grade appliances & abundant storage, flowing seamlessly into bright, open-concept living & dining spaces. A gas fireplace with custom millwork anchors the room, while French doors open to a beautifully landscaped, private rear garden—ideal for relaxing or hosting al fresco. A versatile main-floor room offers flexibility as a home office, den or formal dining room. Upstairs, 3 spacious bedrooms each enjoy their own ensuite with heated floors & walk-in closets—luxury & privacy for all. The lower level with 9' ceilings adds a large family room, 4th bedroom, 3-pc bath & expansive laundry room. Custom built-ins throughout provide exceptional storage. The detached garage includes an EV charger & rare basement storage, while the extra-long driveway accommodates 6 cars. The fully fenced backyard offers a private garden with pretty perennials as well as a stone patio. The unbeatable location places parks, shops, restaurants & the waterfront at your doorstep. Meticulously maintained with thoughtful updates: powder room renovation (2024), driveway resurfaced (2024), exterior freshly stained (2024) & insulation upgraded to R60 (2025). Ideal for empty nesters, downsizers & families alike—this turnkey home is a rare opportunity to experience Oakville's historic charm at its finest.

Location

Province ON

County Halton

Area 1 - Oakville

Zoning RL8 sp:129

Direction Rebecca north on Wilson to Head St

Rooms

Basement Full, Finished, Sump Pump

Bedroom 2 3

Kitchen 1

Interior

Interior Features Central Vacuum, Auto Garage Door Remote(s), Built-In Appliances

Heating Forced Air, Natural Gas

Cooling Central Air

Fireplaces Number 1

Fireplace Yes

Window Features Window Coverings

Appliance Garborator, Dishwasher, Dryer, Gas Oven/Range, Microwave, Range Hood, Refrigerator, Washer

Laundry Lower Level

Exterior

Exterior Feature Landscaped

Parking Features Detached Garage, Garage Door Opener, Asphalt

Garage Spaces 1.0

Fence Full

Waterfront Description River/Stream

Roof Type Asphalt Shing

Porch Patio, Porch

Lot Frontage 40.0

Lot Depth 104.33

Garage Yes

Building

Lot Description Urban, Rectangular, Ample Parking, Park, Quiet Area, Shopping Nearby

Faces Rebecca north on Wilson to Head St

Foundation Poured Concrete

Sewer Sewer (Municipal)

Water Municipal

Architectural Style Two Story

Structure Type Wood Siding

New Construction No

Others

Senior Community No

Tax ID 248190071

Ownership Freehold/None

Virtual Tour https://tours.vogelcreative.ca/listing-preview/105995536

Copyright 2026 Information Technology Systems Ontario, Inc.
Casora Realty
Casora Realty

Agent

+1(905) 332-4111 | hello@casorarealty.ca

GET MORE INFORMATION

Name
Phone*
Message

By checking this box, I agree by electronic signature to the Electronic Disclosure Consent Agreement; to receive recurring marketing communication from Casora Realty, including auto-dialed calls, texts, and artificial/prerecorded voice messages (message frequency varies; data rates may apply; reply "STOP" to opt-out of texts or "HELP" for assistance); and to the Terms of Service and Privacy Policy of this website. Consent not required to make a purchase. I understand that I can call to obtain direct assistance.

Go tour this home

44 Head Street