44 Head St
Central, Oakville
$2,699,000
Buy with Dwelly and Save $26,990
Home Details
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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 moulding & 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.
All appliances, all light fixtures, , all window coverings and blinds, TV bracket in Great Room, Central Vac and all attachments, Dyson Vacuum, Security system ( not currently monitored), garage door opener and remote
City: Oakville
Neighborhood: Central
Property History
| Listing Date | DOM | List Price | Sold Price | Event | MLS ID |
|---|---|---|---|---|---|
| Oct 4, 2012 | 71 | $1,169,000 | $1,047,500 | Sold | W2480449 |
| Jul 13, 2012 | 82 | $1,189,000 | N/A | Terminated | W2417757 |
| Apr 18, 2012 | 84 | $1,249,000 | N/A | Terminated | W2342192 |
| Apr 18, 2012 | N/A | $1,249,000 | N/A | Terminated | O2341706 |
| Jan 18, 2012 | 91 | $1,249,000 | N/A | Expired | W2268532 |
| Sep 24, 2011 | 114 | $1,249,000 | N/A | Expired | W2205221 |
| Sep 25, 2009 | 32 | $439,900 | $419,000 | Sold | O1711948 |
| Feb 20, 2009 | 129 | $424,900 | N/A | Expired | O1563554 |
| Aug 9, 2008 | 76 | $473,900 | N/A | Expired | O1442755 |
Rooms
Room dimensions for 44 Head St, Oakville
Market Trends and Insights
Mortgage Calculator
Your estimated monthly payment for 44 Head St is 14139
Price
$Rate
%Ammortization
Down Payment
$Total Mortgage
| Purchase Price | $2699000 |
| Down Payment | $539800 |
| Mortgage Insurance | $0 |
| Total Mortgage | $2159200 |
Monthly Payment
| Mortgage Payment | $13306 |
| Property Taxes | $833 |
| Maintenance Fees | $0 |
| Monthly Payment | $14139 |
Sold Comparables
Sold Comparables homes near 44 Head St, Oakville
About 44 Head St, Oakville
Located at 44 Head St , this Oakville house is available for sale. This property was listed for $2,699,000 on Thu Jun 26 2025. This house's size is 2000-2500 Sqft. It has 3 bedrooms and 5 bathrooms. The property includes the following rooms: Great Rm, Dining, Kitchen, Office, Bathroom, Primary, Bathroom, 2nd Br, Bathroom, 3rd Br, Bathroom, Rec, 4th Br, Bathroom, Laundry. This property comes with 7 parking spots. 44 Head St, Oakville is situated in the Central neighbourhood.
MLS#: W12246254 · $2,699,000 · 3 bedroom house in Central, Oakville