Detached House for sale at 44 Head Street, Oakville, Ontario, L6K 1L5 - Central - MLS: W12826420

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44 Head Street

Oakville, Ontario, L6K 1L5 - Central

$2,299,000

Virtual Tour

Neighbourhood

Central
Major Intersection

Wilson and Rebecca

Listed Since: 45 day(s)
Last update: 43 day(s) ago

Virtual Tour

Overview

Property Type

Detached, 2-Storey
Bedrooms

3 + 1
Bathrooms

5
Basement

Full + Finished
Kitchen

1
Total Parking

7 (1 Detached Garage)
Lot Size

40x104.33 (Acres)
Taxes

$9,999.00 (2025)
Type

Freehold

Property Description

Property description for 44 Head Street, Oakville

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.

Listed by RE/MAX ABOUTOWNE REALTY CORP.

Property details

MLS #

W12826420
Sq. Ft

2000-2500
Sq. Ft. Source

MLS
Lot Irregularities

n/a
Year Built

6-15
Pool

None
Drive

n/a
Garage

Detached, 1 spaces
Total Parking

7
Family Room

Y
Den

Y
Exterior

Wood
Fireplace

Y
Roof

Asphalt Shingle
Foundation

Poured Concrete
Elevator

n/a
Water View

n/a
Laundry Level

Lower
Heat

Forced Air
A/C

Central Air
Water

Municipal
Water Supply

n/a
Sewers

Sewers
Central Vac

Y

MLS #

W12826420
Sq. Ft

2000-2500
Sq. Ft. Source

MLS
Lot Irregularities

n/a
Year Built

6-15
Pool

None
Drive

n/a
Garage

Detached, 1 spaces
Total Parking

7
Family Room

Y
Den

Y
Exterior

Wood
Fireplace

Y
Roof

Asphalt Shingle
Foundation

Poured Concrete
Elevator

n/a
Water View

n/a
Laundry Level

Lower
Heat

Forced Air
A/C

Central Air
Water

Municipal
Water Supply

n/a
Sewers

Sewers
Central Vac

Y

Great Rm

4.9 x 3.94 ft Main level

Fireplace, hardwood floor, Walk-Out
Dining

4.9 x 2.74 ft Main level

hardwood floor, Walk-Out
Kitchen

5.44 x 3.94 ft Main level

hardwood floor, Granite Counter, Centre Island
Office

3.89 x 4.5 ft Main level

hardwood floor, French Doors
Bathroom

1.12 x 1.47 ft Main level

2 Pc Bath
Primary

3.99 x 4.5 ft 2nd level

W/I Closet, 4 Pc Ensuite
Bathroom

2.51 x 2.82 ft 2nd level

4 Pc Ensuite, Heated Floor, Soaker
2nd Br

4.37 x 3.25 ft 2nd level

W/I Closet, 3 Pc Ensuite
Bathroom

1.83 x 2.11 ft 2nd level

3 Pc Ensuite, Heated Floor
3rd Br

5.23 x 5.69 ft 2nd level

W/I Closet, 4 Pc Ensuite
Bathroom

2.46 x 1.52 ft 2nd level

4 Pc Ensuite, Heated Floor
Rec

5.23 x 4.42 ft Lower level

Pot Lights
4th Br

6.32 x 4.42 ft Lower level
Bathroom

1.45 x 3.1 ft Lower level

3 Pc Bath
Laundry

2.62 x 3.05 ft Lower level

Contact Manoj Kukreja

Sales Representative,
Century 21 People’s Choice Realty Inc.,
Brokerage
(647) 576 - 2100

Open house for 44 Head Street, Oakville

Property History

Property history for 44 Head Street, Oakville

This property has been sold 12 times before. Create your free account to explore sold prices, detailed property history, and more insider data.

Local Real Estate Price Trends for Detached in Central

Active listings

Average Selling Price of a Detached

March 2026

$1,508,833

Last 3 Months

$924,611

Last 12 Months

$1,266,792

March 2025

$2,027,500

Last 3 Months LY

$1,609,722

Last 12 Months LY

$1,668,691

Change

-26%

Change

-43%

Change

-24%

How many days Detached takes to sell (DOM)

March 2026

Last 3 Months

Last 12 Months

March 2025

Last 3 Months LY

Last 12 Months LY

Change

-66%

Change

-22%

Change

-10%

Average Selling price

Mortgage Calculator

This data is for informational purposes only.

Mortgage Payment per month
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Total Payable	Amortization

Property Price

Amortization

Rate of Interest

Down Payment ($)

Down Payment (%)

Closing Cost Calculator

This data is for informational purposes only.

Closing Cost Total for this property

Total Cash flow for purchasing this property

Purchase Price

First time home buyer

Down Payment($)

Down Payment(%)*

Additional information

Provincial Land Transfer Tax

Ontario Land Transfer Tax Rebate

Toronto Land Transfer Tax

Toronto Land Transfer Tax Rebate

PST on CMHC Insurance Premium

Lawyer Fees

$2,825

Government Registration Fee's

$164

Title Insurance

Closing Cost Total

Total Cash flow for purchasing this property

Provincial Land Transfer Tax

Ontario Land Transfer Tax Rebate

Toronto Land Transfer Tax

Toronto Land Transfer Tax Rebate

PST on CMHC Insurance Premium

Lawyer Fees

$2,825

Government Registarion Fee's

$164

Title Insurance

Purchase Price

Down Payment($)

Down Payment(%)*

First time home buyer

* A down payment of less than 20% is permitted only for first-time home buyers purchasing their principal residence. The minimum down payment required is 5% for the portion of the purchase price up to $500,000, and 10% for the portion between $500,000 and $1,500,000. For properties priced over $1,500,000, a minimum down payment of 20% is required.

Contact Manoj Kukreja

Sales Representative, Century 21 People’s Choice Realty Inc., Brokerage
(647) 576 - 2100

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44 Head Street

Overview

Property Description

Thinking of Selling?

Contact Manoj Kukreja

Open house for 44 Head Street, Oakville

Property History

Local Real Estate Price Trends for Detached in Central

Active listings

Average Selling Price of a Detached

How many days Detached takes to sell (DOM)

Average Selling price

Mortgage Calculator

Closing Cost Calculator

Additional information

Thinking of Selling?

Contact Manoj Kukreja

Similar Homes for Sale

152 Chisholm Street

89 Holyrood Avenue

347 Douglas Avenue

197 Glen Oak Drive

1071 Melvin Avenue

321 Wendy Lane

Similar Properties Recently sold

45 Head Street

209 Grenview Boulevard

14 Wendover Road

Recent Sold Listings in Central, Oakville

Popular Cities

Buy

Quick Links

44 Head Street

Overview

Property Description

Property details

Room details

Map

Thinking of Selling?

Contact Manoj Kukreja

Open house for 44 Head Street, Oakville

Property History

Local Real Estate Price Trends for Detached in Central

Active listings

Average Selling Price of a Detached

How many days Detached takes to sell (DOM)

Average Selling price

Mortgage Calculator

Closing Cost Calculator

Additional information

Thinking of Selling?

Contact Manoj Kukreja

Similar Homes for Sale

152 Chisholm Street

89 Holyrood Avenue

347 Douglas Avenue

197 Glen Oak Drive

1071 Melvin Avenue

321 Wendy Lane

Similar Properties Recently sold

45 Head Street

209 Grenview Boulevard

14 Wendover Road

Recent Sold Listings in Central, Oakville

Popular Cities

Buy

Quick Links