44 HEAD STREET,Oakville (CO Central),,

$2,299,000
  • Updated On:
  • April 7, 2026
  • 4 Bedrooms
  • 5 Bathrooms

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:65066)

Address: 44 HEAD STREET
State/County:
Zip: L6K1L5
Country: Canada
Listing Id: W12826420
Price: $2,299,000
Bedrooms: 4
Bathrooms: 5
Basement: Finished, Full
BathroomsPartial: 1
BedroomsAboveGrade: 3
BedroomsBelowGrade: 1
BuildingFeatures: Fireplace(s)
CoListAgentKey: 2237255
CoListOfficeKey: 286883
CommonInterest: Freehold
Cooling: Central air conditioning
Directions: Cross Streets: Wilson and Rebecca. ** Directions: Rebecca to Wilson to Head St.
Fencing: Fenced yard
FireplacesTotal: 1
Flooring: Hardwood
FoundationDetails: Poured Concrete
Heating: Forced air, Natural gas
InternetAddressDisplayYN: 1
InternetEntireListingDisplayYN: 1
ListAOR: Toronto
ListAORKey: 82
ListAgentKey: 2086486
ListOfficeKey: 286883
ListingURL: www.realtor.ca/real-estate/29406685/44-head-street-oakville-co-central-1002-co-central
LivingAreaMaximum: 2500
LivingAreaMinimum: 2000
LivingAreaUnits: square feet
LotSizeDimensions: 40 x 104.3 Acre
ModificationTimestamp: April 7, 2026 at 05:40pm
OriginalEntryTimestamp: February 27, 2026 at 04:14pm
OriginatingSystemName: Toronto Regional Real Estate Board
ParkingFeatures: Detached Garage, Garage
ParkingTotal: 7
PhotosChangeTimestamp: March 11, 2026 at 01:38pm
PhotosCount: 49
PostalCode: L6K1L5
Rooms: Great room: Main level, 4.9 x 3.94 meters | Bathroom: Second level, 2.46 x 1.52 meters | Dining room: Main level, 4.9 x 2.74 meters | Recreational, Games room: Lower level, 5.23 x 4.42 meters | Bedroom 4: Lower level, 6.32 x 4.42 meters | Bathroom: Lower level, 1.45 x 3.1 meters | Laundry room: Lower level, 2.62 x 3.05 meters | Kitchen: Main level, 5.44 x 3.94 meters | Office: Main level, 3.89 x 4.5 meters | Bathroom: Main level, 1.12 x 1.47 meters | Primary Bedroom: Second level, 3.99 x 4.5 meters | Bathroom: Second level, 2.51 x 2.82 meters | Bedroom 2: Second level, 4.37 x 3.25 meters | Bathroom: Second level, 1.83 x 2.11 meters | Bedroom 3: Second level, 5.23 x 5.69 meters
Sewer: Sanitary sewer
StatusChangeTimestamp: April 7, 2026 at 05:26pm
Stories: 2
StreetName: Head
StreetNumber: 44
StreetSuffix: Street
StructureType: House
TaxAnnualAmount: 9999
WaterSource: Municipal water
ZoningDescription: RL8 sp:129
Other Features
Alarm System
Blinds
Central Vacuum
Dishwasher
Dryer
Freezer
Gas stove(s)
Has Fireplace
Microwave
Refrigerator
Washer
Window Coverings
Wood

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$11,787.43
per month
  • Principal and Interest
  • Property Tax
  • HOA fee
  • Private Mortgage Insurance
$ 8,913.68

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