44 HEAD STREET

Oakville, , L6K1L5, Canada

$2,299,000

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 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.

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 : Friday 20th of February 2026 03:00:03 PM

ADDRESS

Street : 44 HEAD STREET

City : Oakville

Country : Canada

Postal Code : L6K1L5

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PROPERTY SUMMARY

Property ID : 40764298

Building Type : House

Property Type : Single Family

Bedrooms : 3 + 1

Bathrooms : 5 + 1

Parking : 7

Parking Type: Detached Garage

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