44 Head Street, Oakville ON

About 44 Head Street

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. (id:56071). Get more information on 44 Head Street

Property Features

Appliances:  Central Vacuum, Dishwasher, Dryer, Garburator, Microwave, Refrigerator, Washer, Range - Gas, Hood Fan, Window Coverings, Garage door opener
Features:  Paved driveway, Sump Pump, Automatic Garage Door Opener
Rental Equipment:  Water Heater
Fireplace Total:  1
Directions:  Rebecca north on Wilson to Head St
Zoning Description:  RL8 sp:129
Interior Size:  3198 sqft
Fence:  Fence
Community Features:  Quiet Area
Lot:  under 1/2 acre
Exterior Finish:  Wood
Water:  Municipal water, Municipal sewage system
Heating / Cooling:   Natural gas / Central air conditioning
Age:  2010
Foundation: Poured Concrete
Construction:  Wood frame
Constructed Date:  2010
Basement:  Full (Finished) Finished

Rooms & Sizes

4pc Bathroom Second level 8 1 x 5 0	Bedroom Second level 17 2 x 12 7	3pc Bathroom Second level 6 0 x 6 11
Bedroom Second level 14 4 x 10 8	4pc Bathroom Second level 8 3 x 9 3	Primary Bedroom Second level 13 1 x 15 7
Laundry room Lower level 8 7 x 10 0	3pc Bathroom Lower level 4 9 x 10 2	Bedroom Lower level 20 9 x 14 6
Recreation room Lower level 17 2 x 18 8	Office Main level 12 9 x 14 9	2pc Bathroom Main level 3 8 x 4 10
Kitchen Main level 17 10 x 12 11	Dining room Main level 16 1 x 9 0	Great room Main level 16 1 x 12 11