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    Home Oakville CO Central 44 Head Street 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    Single Family Residence for sale at 44 Head Street, Oakville, ON, L6K 1L5 - CO Central - MLS: 40823865
    • new
    • for sale

    44 Head Street

    Oakville, ON, L6K 1L5 - CO Central

    $2,299,000

    • Neighbourhood

      CO Central

    • Major Intersection

    • Listed Since: 9 day(s)

    • Last update: today

    Overview

    • Property Type

      Single Family Residence, Two Story

    • Bedrooms

      3 + 1

    • Bathrooms

      5

    • Basement

      Full, Finished, Sump Pump

    • Kitchen

      n/a

    • Total Parking

      7 (1 null Garage)

    • Lot Size

      40.00x104.33 (Square Feet)

    • Taxes

      $9,999.00 (2025)

    • Type

      Freehold

    Property Description

    Property description for 44 Head Street, Oakville

    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.

    Listed by RE/MAX Aboutowne Realty Corp.

    Property details
    Room details
    Map

    • MLS #

      40823865

    • Sq. Ft

      3198

    • Sq. Ft. Source

      MLS

    • Lot Irregularities

      n/a

    • Year Built

      2010

    • Pool

      n/a

    • Drive

      n/a

    • Garage

      n/a

    • Total Parking

      7

    • Family Room

      n/a

    • Den

      n/a

    • Exterior

      Wood Siding

    • Fireplace

      1

    • Roof

      Asphalt Shing

    • Foundation

      Poured Concrete

    • Elevator

      n/a

    • Water View

      n/a

    • Laundry Level

      n/a

    • Heat

      Forced Air, Natural Gas

    • A/C

      Central Air

    • Water

      Municipal

    • Water Supply

      n/a

    • Sewers

      n/a

    • Central Vac

      Y

    • Dining Room

      4.90 x 2.74 ft Main level

      crown moulding, french doors, hardwood floor

    • Recreation Room

      5.23 x 5.69 ft Lower level

    • Bedroom

      5.23 x 3.84 ft Second level

      ensuite, walk-in closet

    • Bathroom

      2.51 x 2.82 ft Second level

      4-piece, ensuite, heated floor

    • Office

      3.89 x 4.50 ft Main level

      crown moulding, french doors, hardwood floor

    • Bedroom

      6.32 x 4.42 ft Lower level

    • Bathroom

      1.12 x 1.47 ft Main level

      2-Piece

    • Bathroom

      1.83 x 2.11 ft Second level

      3-piece, ensuite, heated floor

    • Great Room

      4.90 x 3.94 ft Main level

      crown moulding, fireplace, french doors

    • Laundry

      2.62 x 3.05 ft Lower level

    • Bedroom

      4.37 x 3.25 ft Second level

      ensuite, walk-in closet

    • Bathroom

      2.46 x 1.52 ft Second level

      4-piece, ensuite, heated floor

    • Bedroom Primary

      3.99 x 4.75 ft Second level

      ensuite, walk-in closet

    • Bathroom

      1.45 x 3.10 ft Lower level

      3-Piece

    • Kitchen

      5.44 x 3.94 ft Main level

      crown moulding, hardwood floor

    • MLS #

      40823865

    • Sq. Ft

      3198

    • Sq. Ft. Source

      MLS

    • Lot Irregularities

      n/a

    • Year Built

      2010

    • Pool

      n/a

    • Drive

      n/a

    • Garage

      n/a

    • Total Parking

      7

    • Family Room

      n/a

    • Den

      n/a

    • Exterior

      Wood Siding

    • Fireplace

      1

    • Roof

      Asphalt Shing

    • Foundation

      Poured Concrete

    • Elevator

      n/a

    • Water View

      n/a

    • Laundry Level

      n/a

    • Heat

      Forced Air, Natural Gas

    • A/C

      Central Air

    • Water

      Municipal

    • Water Supply

      n/a

    • Sewers

      n/a

    • Central Vac

      Y

    • Dining Room

      4.90 x 2.74 ft Main level

      crown moulding, french doors, hardwood floor

    • Recreation Room

      5.23 x 5.69 ft Lower level

    • Bedroom

      5.23 x 3.84 ft Second level

      ensuite, walk-in closet

    • Bathroom

      2.51 x 2.82 ft Second level

      4-piece, ensuite, heated floor

    • Office

      3.89 x 4.50 ft Main level

      crown moulding, french doors, hardwood floor

    • Bedroom

      6.32 x 4.42 ft Lower level

    • Bathroom

      1.12 x 1.47 ft Main level

      2-Piece

    • Bathroom

      1.83 x 2.11 ft Second level

      3-piece, ensuite, heated floor

    • Great Room

      4.90 x 3.94 ft Main level

      crown moulding, fireplace, french doors

    • Laundry

      2.62 x 3.05 ft Lower level

    • Bedroom

      4.37 x 3.25 ft Second level

      ensuite, walk-in closet

    • Bathroom

      2.46 x 1.52 ft Second level

      4-piece, ensuite, heated floor

    • Bedroom Primary

      3.99 x 4.75 ft Second level

      ensuite, walk-in closet

    • Bathroom

      1.45 x 3.10 ft Lower level

      3-Piece

    • Kitchen

      5.44 x 3.94 ft Main level

      crown moulding, hardwood floor

    Thinking of Selling?

    Find Out Your Home’s Value in Today’s Market!

    No Email or Signup is required to view your home estimate.

    estimate your home value

    Contact Manoj Kukreja

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

    Manoj profile avatar

    Open house for 44 Head Street, Oakville

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    Property History

    Property history for 44 Head Street, Oakville

    This property has been sold 3 times before. Create your free account to explore sold prices, detailed property history, and more insider data.

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    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

    Down Payment(%)*

    * 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.

    Thinking of Selling?

    Find Out Your Home’s Value in Today’s Market!

    No Email or Signup is required to view your home estimate.

    estimate your home value

    Contact Manoj Kukreja

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

    Manoj profile avatar

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