$2,299,000
Listed for $2,299,000 on Sep. 04, 2025

44 Head Street

Oakville

4 Bed|5 Bath|Yes|209 days on market

$2,299,000

Listed for $2,299,000 on Sept 4, 2025

Or call Dwelly at: (647) 797-1133

Home Details

Taxes
$834 / month
Total Parking Spots
7
Garage Spaces
6
Furnished
No
Move-in Date
Early Oct preferred
Hydro Included
No
Heating
Forced Air
Water Included
No
Family Room
Yes
Basement
Full, Finished
Fireplace
Y
Air Conditioning
Central Air
Central Vaccum
No
Exterior
Wood
Zoning
RL8 sp:129
Sewer
Sewer
Property Type
Residential Freehold

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 molding & 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

About 44 Head Street, Oakville

Located at 44 Head Street , this Oakville house was listed for $2,299,000. It has 4 bedrooms and 5 bathrooms. The property's amenities include Electric Car Charger, Fenced Yard, Public Transit. The property includes the following rooms: . This property comes with 7 parking spots.


MLS#: undefined · $2,299,000 · 4 bedroom house in Oakville