44 Head St

Oakville, ON L6K 1L5
  • $2,299,000

    Price
  • 4

    Bed
  • 5

    Bath
  • 2,183

    SqFt

About the Listing HBREMAXABT2 - HBBLAHALA

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.

Listing Highlights

Status Active
Days on Site 2
Property Type Residential
MLS ® 40808082
Year Built 2010
Total Square Footage 2,183
Lot/Acreage 40 x 104.33

Interior Details

  • Bedrooms: 4
  • Bathrooms: 4 Full / 1 Half
  • Appliances: Garborator, Dishwasher, Dryer, Gas Oven/Range, Microwave, Range Hood, Refrigerator, Washer
  • Air Cond: Central Air
  • Heating: Forced Air,Natural Gas
  • Fireplaces: 1
  • Floor:
  • Above Ground Sq Ft: 2183
  • Below Ground Sq Ft: 1015
  • Basement: Full,Finished,Sump Pump
  • Other: Central Vacuum,Auto Garage Door Remote(s),Built-In Appliances
  • Water: Municipal

Exterior Details

  • Lot Description: Urban,Rectangular,Ample Parking,Park,Quiet Area,Shopping Nearby
  • Garage Capacity: 1 car
  • Parking Spaces: 7
  • Lot Dimensions: 40 x 104.33
  • Zoning: RL8 sp:129
  • Roof: Asphalt Shing
  • Others: Landscaped
  • Sewer: Sewer (Municipal)
  • Parking Features: Private Drive Single Wide,Detached Garage,Garage Door Opener,Asphalt

Financial Details

  • Tax Amount: N/A
  • Taxes w/Assessments: N/A
  • Tax/Property ID: 248190071
  • Tax Year: N/A

Payment Calculator

Monthly Payment

  • in Principal and Interest
  • in Taxes
Years
% Down Payment
% Mortgage Rate

Questions About..

44 Head St Oakville, ON L6K 1L5

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Never Miss A New Property

Get notified any time there's a new home on the market in this neighborhood!

Don't worry! We'll never spam you or sell your details. You can unsubscribe whenever you'd like.

Originating MLS: Cornerstone

|

home

Are you buying or selling a home?

Buying
Selling
Both
home

When are you planning on buying a new home?

1-3 Mo
3-6 Mo
6+ Mo
home

Are you pre-approved for a mortgage?

Yes
No
Using Cash
home

Would you like to schedule a consultation now?

Yes
No

When would you like us to call?

Thanks! We’ll give you a call as soon as possible.

home

When are you planning on selling your home?

1-3 Mo
3-6 Mo
6+ Mo

Would you like to schedule a consultation or see your home value?

Schedule Consultation
My Home Value

or another way