$2,299,000
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44 Head Street, Oakville, ON L6K1L5

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4 Beds
5 Baths
3,198 Sq Ft
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Sun, 6/07
6 PM - 8 PM

Welcome to 44 Head Stan exceptional residence in the heart of Oakvillejust steps to Kerr Village, downtown boutiques, cafs & 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 porchperfect for morning coffee or evening wine. Inside, 9' ceilings, hardwood floors, crown moulding & high baseboards create an elevated aesthetic. The entertainers 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 gardenideal 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 closetsluxury & 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 alikethis turnkey home is a rare opportunity to experience Oakvilles historic charm at its finest. (id:58753)

Listing By: Laurie Blaha - RE/MAX Aboutowne Realty Corp. cncrea2 Realty.com
  • MLS® 40823865
  • Date Listed04/25/2026
  • Days on Realty 42 Days
  • Bedrooms 4
  • Bathrooms 5 baths
  • Lot Size -
  • Sewer Public Sewer
  • Subdivision 1002 - CO Central
  • Property Type Single Family Residence
  • Year Built 2010
  • Water Public
  • Square Feet 3,198 sq. ft
  • Price Per Sq. Ft $718.89

Interior Features

  • Appliances Washer, Refrigerator, Central Vacuum, Range - Gas, Dishwasher, Dryer, Microwave, Garburator, Hood Fan, Window Coverings, Garage door opener
  • Cooling Central air conditioning
  • Heating Forced air, Natural gas

Exterior / Lot Features

  • Roof -
  • Lot Size Acres -
  • Lot Size SQFT -
  • Lot Features Paved driveway, Sump Pump, Automatic Garage Door Opener

Directions

Rebecca north on Wilson to Head St

Sales & Tax History

Source: Public Records

Local Neighborhood Highlights for L6K1L5

Discover key demographics, population statistics, and environmental insights for the Oakville, ON area.

Walkability in ON / L6K1L5

Source: Walk Score

87/100

Very Walkable

Walk Score ®

43/100

Some Transit

Transit Score ®

70/100

Very Bikeable

Bike Score ®

Overview

Most errands can be accomplished on foot. A few nearby public transportation options. Biking is convenient for most trips.

Transit Summary

8 nearby routes: 8 bus, 0 rail, 0 other

Walkability averages in the surrounding area

The average walkability score in the surrounding area is Walk Score: 40/100, Transit Score: 39/100, Bike Score: 52/100.

Points of Interest near 44 HEAD Street, Oakville, ON L6K1L5

Frequently Asked Questions for 44 HEAD Street

Source: Realty.com

44 HEAD Street, Oakville, ON L6K1L5 in 1002 - CO Central, Oakville, ON L6K1L5 is a single family residence listed at $2,299,000. Highlights include 4 bedrooms, 5 bathrooms, 3,198 sq. ft., built in 2010, $719 per sq. ft.. Realty.ca has 50 photos, sales history, school insights, and mortgage tools for this listing.

Realty.com has 50 photos of 44 HEAD Street.

Our records indicate that 44 HEAD Street was built in 2010.

The full address for this home is 44 HEAD Street, Oakville, ON L6K1L5.

44 HEAD Street has been listed on Realty.com since Sat April 25, 2026

Most errands can be accomplished on foot. A few nearby public transportation options. Biking is convenient for most trips.

The average walkability score in the surrounding area is Walk Score: 40/100, Transit Score: 39/100, Bike Score: 52/100.

Listing provided courtesy of: RE/MAX Aboutowne Realty Corp.
Listing agent: Laurie Blaha

This content last refreshed on 2026-06-06 10:25:11. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.