44 Head Street
1002 - CO Central, Oakville, L6K 1L5
FOR SALE
$2,299,000
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Property 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 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, cafes & 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.
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Sold History
| List Date | Sold Date | Days Listed | List Price | Sold Price |
|---|---|---|---|---|
| 2009-09-25 | 2009-10-27 | 32 | $439,900 | $419,000 |
| 2001-09-06 | 2001-09-06 | 0 | $184,500 | $184,500 |
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Property Features
Electric Car Charger, Fenced Yard, Public Transit, Central Vacuum, Natural Gas
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Property Details
Address
44 Head Street
Community
City
Postal Code
L6K 1L5
Property Type
Detached, Detached
Zoning
RL8 sp:129
Lot Size
40' x 104'
Acreage
0.1 Acres
Taxes
$9,999 (2025
Basement
Full, Finished
Exterior
Porch, Patio
Heat Type
Forced Air
Heat Source
Gas
Water
Municipal
Parking Spaces
6
Garage Type
Detached
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Listing contracted with Re/Max Aboutowne Realty Corp.
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Rare Find! Prime Joshua Creek executive home with premium extra deep private lot nestled on a quiet family friendly street. A truly bright and airy home with soaring cathedral ceilings, light hardwood, loads of windows, open concept layout, spacious separate living & dining rooms, and the perfect home office complete with built-ins & extra high ceilings. The heart of this home is the chef inspired eat-in kitchen with high end Jenn Air stainless steel appliances overlooking the garden oasis with salt water pool. Upstairs, all 4 generous bedrooms have ensuite privileges. The carpet free lower level boasts a cozy rec room with gas fireplace, exercise area, and 5th bedroom with ensuite & walk-in closet. Located in Frazier top ranked Iroquois Ridge high school & Joshua Creek Public School school districts. Recent improvements include Furnace & A/C '25, Roof '19, Pool Heater '23, Pool Pump & Salt System '22, Pool Safety Cover '17. Close to superb walking trails, parks, shops, and highways. A fantastic place to raise your family!
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Recently reimagined for modern family living, this West Oakville residence blends refined architectural design with a resort-style backyard retreat, all just minutes from the lake. Offering 4+1 bedrooms, 4.5 bathrooms, and a finished lower level, the home delivers a seamless balance of style, comfort, and functionality. The main level is defined by engineered hardwood flooring, expansive floor-to-ceiling windows, and open-concept principal rooms designed for everyday living and entertaining. The custom kitchen showcases quartz countertops, a large centre island with sink, JennAir gas range, pot filler, and effortless flow to the backyard. An open-riser staircase with glass panels adds architectural interest, while the living area is anchored by a feature wall with gas fireplace. Upstairs, engineered hardwood flooring continues throughout. The primary suite offers an accent wall, wall sconces, a walk-in closet with built-ins and window, and a spa-inspired ensuite featuring a freestanding tub, glass shower with rainfall showerhead, and double sinks. A second bedroom enjoys its own private three-piece ensuite, while two additional bedrooms share a well-appointed four-piece bath. A convenient laundry room with sink completes the upper level. Outdoors, the fully fenced backyard is a true showpiece. Designed for entertaining and relaxation, it features an inground pool with an eco-friendly and cost-effective copper ionizer system, extensive stone hardscaping, and a covered outdoor living area with gas fireplace. A dedicated BBQ area with gas line and direct side-door access to the kitchen enhances both convenience and functionality. Ideally situated near parks, Gladys Speers Public School, St. Dominic Catholic Elementary School, Queen Elizabeth Park Community and Cultural Centre, shopping, transit, major highways, and the lake, this home offers an exceptional lifestyle in a vibrant, family-friendly community. (certain exterior images have been digitally enhanced)
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PREMIUM RAVINE LOT IN SOUGHT-AFTER GLEN ABBEY! Designed for family living and entertaining, the private backyard oasis features a raised composite deck with awning, stamped concrete patio, inground saltwater pool, outdoor cabana with plumbing and electrical, and new fencing. The main level welcomes you with a dramatic two-storey foyer, formal living room with gas fireplace and custom built-ins, private office with French door entry, and dining room with custom bar. The stunning gourmet kitchen is equipped with granite countertops, premium appliances, and a large centre island with seating, flowing seamlessly into the family room featuring a gas fireplace and double French door walkout to the deck. The oversized primary retreat features two walk-in closets and a luxurious five-piece ensuite with double sinks, glass shower, and freestanding tub. Three additional bedrooms and a spa-inspired three-piece bathroom complete the upper level. The professionally finished basement is ideal for a growing family, offering a spacious recreation/games area with electric fireplace and bar, exercise area, contemporary three-piece bathroom, and ample storage. Improvements within the past six years include engineered hardwood flooring, staircase with decorative iron spindles, renovated bathrooms, eavestroughs and downspouts, and a stamped concrete driveway, walkway, and patio (2023). Additional highlights include custom closet organizers, solid wood interior doors, updated laundry room with garage access, and onsite parking for four cars. Located in a desirable family-friendly neighbourhood surrounded by parks and trails, and within walking distance of Pilgrim Wood Public School and top-ranked Abbey Park High School. Close to community centre, shopping, dining, hospital, major highways, GO Train, and everyday amenities. An extensively updated residence backing onto a ravine in one of Oakville's most coveted communities. (certain images have been digitally enhanced)
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Welcome To This Stunning Mattamy-Built Windfield Model Situated On A Premium Front and Back Ravine Lot With Serene Water Views Near The Pond In One Of Oakville's Most Sought-After Communities. Thoughtfully Designed For Modern Family Living, This Beautiful Home Offers A Functional And Elegant Layout Filled With Natural Light And Exceptional Living Spaces Throughout. The Main Floor Features A Welcoming Covered Porch, Spacious Foyer, Formal Dining Room, And An Open-Concept Great Room 20 ft high With Electric Fireplace Overlooking The Scenic Backyard. The Chef-Inspired Kitchen Includes A Large Centre Island, Ample Cabinetry, And A Bright Breakfast Area With Walk-Out To The Backyard - Perfect For Entertaining And Everyday Living. A Convenient Mudroom With Garage Access, Walk-In Closet, And Tucked-Away Powder Room Complete The Main Level. The Second Floor Offers A Versatile Loft/Home Office Space Ideal For Remote Work Or Relaxation. The Spacious Primary Retreat Features 10 ft High and A Walk-In Closet And A Luxurious Ensuite Bath. Three Additional Bedrooms, Including One Ideal As A Secondary Home Office, Along With A Full Bathroom And Convenient Upper-Level Laundry Room Provide Comfort And Functionality For The Entire Family. Enjoy Premium Ravine Living Close To Parks, Trails, Top-Rated Schools, Shopping, Hospital, Transit, GO Station, And Major Highways. A Rare Opportunity To Own A Beautiful Family Home In A Highly Desirable North Oakville Location. Basement features a finished sitting area and no wasted space with 9 ft high ceiling in upgrades.
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