44 Head Street
1002 - CO Central, Oakville, L6K 1L5
FOR SALE
$2,399,000

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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 molding & high baseboards create a refined, elevated feel. The entertainers 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 4th bedroom, 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
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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 |
Nearby Intersections
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
Days On Market
83
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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Wow-This Is An Absolute Showstopper And A Must-See! Priced To Sell Immediately! This Stunning 4+1 Bedroom, 5-Washroom Residence With An Open-To-Above Foyer Sits On A Premium Lot In Oakville, Offering Approx. 3,200 Sq Ft Plus A 671 Sq Ft Legal 1-Bedroom Basement Apartment Finished By The Builder! Elegance Greets You With Premium Hardwood On The Main And Second Levels, A Hardwood Oak Staircase With Upgraded Wainscoting, 10' Ceilings On The Main, 9' On The Second, And 9' In The Basement, All Elevated By Designer Light Fixtures For A Luxe Ambiance. The Chef's Gourmet Kitchen Shines With A Large Center Island, Quartz Countertops, Sleek Backsplash, Wine Fridge, And Top-Tier Built-In Stainless Steel Appliances. Seamlessly Connected Is The Cozy Family Room Featuring A Gas Fireplace And Custom Waffle Ceiling-The Perfect Setting For Relaxing Nights Or Memorable Gatherings. Retreat To The Primary Suite, A Private Haven With A Walk-In Closet And Spa-Inspired 6-Piece Ensuite; A Striking Feature Wall Adds Style And Personality. The Second Level Is Designed For Comfort And Productivity With 4 Spacious Bedrooms, 3 Full Bathrooms, And Convenient Second-Floor Laundry. The Legal Finished Basement Impresses With A Separate 1-Bedroom Suite Complete With Kitchen And Full Washroom-Ideal For Extended Family, Guests, Or Potential Rental Income. Thoughtful Details And Quality Finishes Are Evident In Every Room, Delivering The Space, Style, And Function Today's Buyers Demand. This Home Truly Checks Every Box-Location, Luxury, And Layout. Don't Miss It!
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Rare opportunity to own a premium lot backing onto tranquil, protected green space! Welcome to 1464 Varelas Passage, a sophisticated and stunning residence, located in one of Oakville's most upscale and coveted neighbourhoods, Joshua Meadows. Enjoy a spacious Windfield model floor plan (3109 sq.ft), this home defines contemporary elegance, featuring soaring 10' ceilings on the main floor, 9' ceilings on the second level, and a professionally finished basement with upgraded raised ceilings. The sun-filled, open-concept floor plan is anchored by rich hardwood flooring and a chef-inspired kitchen. Culinary enthusiasts will love the organic white caesarstone countertops, designer backsplash, and premium integrated appliance package. The inviting living room, centered around a sleek gas fireplace, offers the perfect ambiance for hosting. The second level is thoughtfully designed with four spacious bedrooms and three full baths. The lavish primary suite features a walk-in closet and a spa-like 5-piece ensuite. A rare secondary junior suite also boasts its own private ensuite, providing comfort for guests or multi-generational living. The lower level extends your living space significantly, featuring a 5th bedroom, a full bathroom, a dedicated study/office, and a large recreation room. The exterior matches the interior's excellence with new interlocking and professional landscaping- creating stunning curb appeal. This luxurious home is in pristine, move-in condition. Location is everything: Situated at the Mississauga/Oakville border, it's a short drive to both Clarkson and Oakville GO Stations, and a 5-7 minute drive to other amenities including Walmart, Superstore, Longo's, premium gyms, and scenic parks. Experience the perfect blend of new-construction peace of mind with the best in luxury finishes. This is where brand-new serenity meets high-end style.
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An Exceptional Fernbrook Carnegie Model in the Prestigious Glenorchy Community, ideally situated across from a beautiful park. This elegant 4+1 bedroom, 5-bath residence offers 2,963 sq. ft. of refined living space above grade, plus a professionally finished basement. Built in 2018, the home showcases a striking stone and stucco exterior and premium upgrades throughout. The open-concept design features 10-foot ceilings on the main level, coffered ceilings, and a chef-inspired kitchen with quartz countertops, high-end appliances, a large island, and custom coffee bar. The upper level offers four spacious bedrooms with ensuite or semi-ensuite access, including a luxurious primary suite with spa-like ensuite and walk-in closet. The finished basement includes a recreation area, fireplace, bar, additional bedroom, and full bath. Enjoy a beautifully landscaped backyard with a custom pergola, all in a sought-after location close to top schools, trails, shopping, and transit.
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Welcome to this beautifully updated and meticulously maintained family home, ideally situated on a quiet, child-friendly street in the highly sought-after River Oaks community. Offering over 4500 sqft of total living space, this impressive 4-bedroom, 5-bathroom residence is perfectly designed for both everyday family living and entertaining. The main level features a spacious entry foyer with high end Italian tiles and hardwood flooring , traditional living and dining rooms, and an open-concept kitchen complete with a walk-in pantry, eat-in area, and walkout to a private backyard oasis. An oversized family room, home office/den, powder room, and convenient main-floor laundry with garage and exterior access complete this level. Upstairs, the exceptional primary suite boasts a walk-in closet and spa-like ensuite. Three additional generously sized bedrooms complete the second floor, including a unique fourth bedroom with its own sitting nook and 2-piece ensuite-ideal for teens or guests. The fully finished lower level offers a large recreation room, gym area, 3-piece bathroom, and ample storage. Step outside to your private backyard, no maintenance retreat featuring an inground saltwater pool with solar panel heating, interlock patio, perfect for summer entertaining. Notable updates include furnace (2009), windows (2008), California shutters, salt cell (2025), and A/C (rental, 2025). A truly exceptional home in a prime family-friendly location.
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