44 HEAD STREET

Oakville, , L6K1L5, Canada

$2,299,000

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.

EXTRAS: Washer, Refrigerator, Central Vacuum, Range - Gas, Dishwasher, Dryer, Microwave, Garburator, Hood Fan, Window Coverings, Garage door opener

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

Last updated on : Thursday 30th of April 2026 07:55:10 AM

ADDRESS

Street : 44 HEAD STREET

City : Oakville

Country : Canada

Postal Code : L6K1L5

Open in Google Map

PROPERTY SUMMARY

Property ID : 40823865

Building Type : House

Property Type : Single Family

Bedrooms : 3 + 1

Bathrooms : 5 + 1

Parking : 7

Parking Type: Detached Garage

Similar Properties

Single Family

34 HASKINS CRESCENT

Georgina (Keswick South), Ontario, L4P2G6

$885,000

Beds: 3Baths: 4

property Type: House

type: Sale

HARRY SIU
1 month ago

DETAILS

Single Family

104 RIDGEVIEW DRIVE

Blue Mountains, Ontario, L9Y3Z2

$1,049,000

Beds: 3Baths: 1

property Type: House

type: Sale

JANET NIELSEN
4 months ago

DETAILS

Single Family

43342 AMBERLEY ROAD

Wroxeter, Ontario, N0G2X0

$799,900

Beds: 3Baths: 2

property Type: House

type: Sale

David Meulensteen
1 month ago

DETAILS

Single Family

7 PRINCE CHARLES DRIVE

St. Catharines, Ontario, L2N3Y4

$749,900

Beds: 3Baths: 2

property Type: House

type: Sale

Natalie Butler
1 month ago

DETAILS

Single Family

1357 MICHAEL CIRCLE

London, Ontario, N5V0B8

$635,000

Beds: 3Baths: 4

property Type: Row / Townhouse

type: Sale

Jyoti Joshi
2 months ago

DETAILS

Inquire about this property