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44 HEAD STREET, Oakville (CO Central), Ontario, L6K1L5

MLS: W12826420 | House (Freehold)

$2,299,000

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Property 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 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 4thbedroom, 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. (id:64974)

Directions: Cross Streets: Wilson and Rebecca. ** Directions: Rebecca to Wilson to Head St.

Quick Facts

  • Property Type: House (Freehold)
  • Bedrooms: 4 (3 above, 1 below)
  • Bathrooms: 5 (1 half)
  • Ownership: Freehold
  • Attached: No
  • Fireplaces: 1
  • Parking: 7 spaces (Detached Garage, Garage)

Costs

  • Annual Taxes: $9,999.00

Listing Provided by: RE/MAX ABOUTOWNE REALTY CORP.
Board: Toronto Regional Real Estate Board
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, Gas stove(s), Dishwasher, Dryer, Microwave, Alarm System, Freezer, Blinds, Window Coverings
  • Flooring: Hardwood

Exterior & Construction

  • Exterior: Wood
  • Foundation: Poured Concrete
  • Fencing: Fenced yard
  • Sewer: Sanitary sewer
  • Water: Municipal water

Lot & Land

  • Zoning: RL8 sp:129

Community & Neighbourhood

  • Building: Fireplace(s)
  • Neighbourhood: 1002 - CO Central

Room Details (15 rooms)

Main level
Great room16'1" x 12'11" (208 ft²)
Dining room16'1" x 9'0" (145 ft²)
Kitchen17'10" x 12'11" (231 ft²)
Office12'9" x 14'9" (188 ft²)
Bathroom3'8" x 4'10" (18 ft²)
Second level
Bathroom8'1" x 5'0" (40 ft²)
Primary Bedroom13'1" x 14'9" (193 ft²)
Bathroom8'3" x 9'3" (76 ft²)
Bedroom 214'4" x 10'8" (153 ft²)
Bathroom6'0" x 6'11" (42 ft²)
Bedroom 317'2" x 18'8" (320 ft²)
Lower level
Recreational, Games room17'2" x 14'6" (249 ft²)
Bedroom 420'9" x 14'6" (301 ft²)
Bathroom4'9" x 10'2" (48 ft²)
Laundry room8'7" x 10'0" (86 ft²)

Listing Information

MLS® NumberW12826420
BoardToronto
Originating SystemToronto Regional Real Estate Board
BrokerageRE/MAX ABOUTOWNE REALTY CORP.
Date ListedFebruary 27, 2026
Last UpdatedMarch 11, 2026

Listing History

Buy/Sell/Terminated/Expired listing history for 44 HEAD STREET, Oakville (CO Central), Ontario, L6K1L5

DateDays on MarketPriceEventListing ID
🔄3/11/202611Status ChangedW12826420
2/27/20260$2,299,000For SaleW12826420
2/27/20260$2,299,000ListedW12826420

Location & Neighborhood

📍44 HEAD STREET, Oakville, Ontario, L6K1L5
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