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44 HEAD Street, Oakville, Ontario, L6K1L5

MLS: 40823865 | House (Freehold)

$2,299,000

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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. (id:64974)

Directions: Rebecca north on Wilson to Head St

Quick Facts

  • Property Type: House (Freehold)
  • Style: 2 Level
  • Bedrooms: 4 (3 above, 1 below)
  • Bathrooms: 5 (1 half)
  • Living Area: 3,198 sq ft (297.1 m²)
  • Above Grade: 2,183 sq ft (202.8 m²)
  • Below Grade: 1,015 sq ft (94.3 m²)
  • Year Built: 2010
  • Ownership: Freehold
  • Attached: No
  • Fireplaces: 1
  • Parking: 7.0 spaces (Detached Garage)
  • Frontage: 40 ft (12.2 m)

Costs

  • Annual Taxes: $9,999.00

Listing Provided by: RE/MAX Aboutowne Realty Corp.
Board: Cornerstone Association of REALTORS®
Data provided via CREA DDF®.

Detailed Features

Interior & Systems

  • Heating: Forced air, Natural gas
  • Cooling: Central air conditioning
  • Basement: Finished, Full
  • Appliances: Washer, Refrigerator, Central Vacuum, Range - Gas, Dishwasher, Dryer, Microwave, Garburator, Hood Fan, Window Coverings, Garage door opener

Exterior & Construction

  • Style: 2 Level
  • Exterior: Wood
  • Construction: Wood frame
  • Foundation: Poured Concrete
  • Fencing: Fence
  • Sewer: Municipal sewage system
  • Water: Municipal water

Lot & Land

  • Frontage: 40 ft (12.2 m)
  • Features: Paved driveway, Sump Pump, Automatic Garage Door Opener
  • Zoning: RL8 sp:129

Community & Neighbourhood

  • Community: Quiet Area
  • Subdivision: 1002 - CO Central

Room Details (15 rooms)

Lower level
Laundry room10'0" x 8'7" (86 ft²)
3pc Bathroom10'2" x 4'9" (48 ft²)
Bedroom14'6" x 20'9" (301 ft²)
Recreation room18'8" x 17'2" (320 ft²)
Second level
4pc Bathroom5'0" x 8'1" (40 ft²)
Bedroom12'7" x 17'2" (216 ft²)
3pc Bathroom6'11" x 6'0" (42 ft²)
Bedroom10'8" x 14'4" (153 ft²)
4pc Bathroom9'3" x 8'3" (76 ft²)
Primary Bedroom15'7" x 13'1" (204 ft²)
Main level
Office14'9" x 12'9" (188 ft²)
2pc Bathroom4'10" x 3'8" (18 ft²)
Kitchen12'11" x 17'10" (230 ft²)
Dining room9'0" x 16'1" (145 ft²)
Great room12'11" x 16'1" (208 ft²)

Listing Information

MLS® Number40823865
BoardCornerstone
Originating SystemCornerstone Association of REALTORS®
BrokerageRE/MAX Aboutowne Realty Corp.
Date ListedApril 25, 2026
Last UpdatedMay 2, 2026

Listing History

MLS listing activity for 44 HEAD Street, Oakville, Ontario, L6K1L5 — dates reflect when changes were recorded in the DDF

DateDays on MarketPriceEventListing ID
🔄5/2/20267Status Changed40823865
4/25/20260$2,299,000Listed (For Sale)40823865

Location & Neighborhood

📍44 HEAD Street, Oakville, Ontario, L6K1L5

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Cathy Dou
Cathy Dou
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[email protected]647-691-6364
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44 HEAD Street, Oakville, Ontario, L6K1L5

ASAP
 
MON
4
May
TUE
5
May
WED
6
May
THU
7
May
FRI
8
May
SAT
9
May
SUN
10
May
MorningAfternoonEvening
Cathy Dou
Cathy Dou
Broker of Record
[email protected]647-691-6364
Ask a Question