Listed by Re/Max Aboutowne Realty Corp..

44 Head Street is a Detached, 2-Storey and is currently for Sale @ $2,399,000. Taxes in 2025 were $9,999.00.

More homes for sale under 2.4M in Oakville

Welcome to 44 Head St - an exceptional home in the heart of Oakville- steps from Kerr Village & downtown. The 2-Storey on 44 Head Street has 3 bedrooms, 5 bathrooms, and is located on a 104.33 x 40 ft lot in the community of Central . 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

All appliances, all light fixtures, all window coverings and blinds, TV bracket in Great room, central vac & attachments, Dyson Vacuum, security system ( not currently monitored), garage door opener & remote

The address 44 Head Street was listed for sale (MLS# W12379865) on Thursday, September 04, 2025.