$1,799,900 - 2371 Calloway Drive, Oakville
Detached for Sale in Oakville
Neighbourhood: 1019 - WM Westmount
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- MLS Number
- W13771036
- Property Type
- Detached
- Status
- active
- Days on Site
- 27
- Bedrooms
- 5
- Bathrooms
- 5
- Square Feet
- 3,000 - 3,499 sqft
- Neighbourhood
- Oakville
- Taxes (2025)
- $8,488
- Listing Brokerage
- CENTURY 21 MILLER REAL ESTATE LTD.
Set against lush greenspace and scenic walking trails, this extensively updated Westmount home offers a beautiful setting and over 4,260 sq. ft. of finished living space. Extensively renovated in 2023 and situated on a premium landscaped lot, the home features hardwood flooring throughout the main living areas, upper hall and all bedrooms, along with crown moulding, California shutters and neutral décor. The main level offers a private office, combined living and dining room, and a bright family room with coffered ceilings and gas fireplace, open to the chef-inspired kitchen and breakfast area. The kitchen features an oversized quartz island with breakfast bar and waterfall edge, quartz backsplash, extended custom white cabinetry with glass display accents, walk-in pantry, S/S appliances, undermount sink, designer pendant lighting, pot lights and large-format porcelain tile flooring. Surrounded by windows, the breakfast area walks out to a spacious deck and fully fenced backyard overlooking tranquil greenspace. Upstairs are 4 spacious bedrooms, including a primary retreat with 2 walk-in closets and spa-inspired ensuite with double sinks, large glass shower, soaker tub and water closet. Bedrooms 2 and 3 share a semi-ensuite 4-pc bath, with an additional 4-pc bath and upper-level laundry featuring built-in cabinetry, counter space, utility sink and new side-by-side washer and dryer. The finished basement offers laminate flooring, pot lights, a large rec room, 5th bedroom and full bath. Additional features include upgraded insulation, central vacuum, roof (2018), double garage with inside entry and double driveway. Close to top-rated schools, parks, trails, shopping, transit, Oakville Trafalgar Hospital and major highways.
Estimate your monthly payments for this property
Estimated Payment
$7,961.56/mo
5-yr fixed avg.
Rates shown are estimates based on typical Ontario 5-year fixed rates. Canadian mortgages use semi-annual compounding as required by law. CMHC insurance applies to purchases under $1.5M with less than 20% down. Estimated property tax uses an approximate 0.85% rate. Contact us for current rate options and pre-approval.
Discover 1019 - WM Westmount
1019 - WM Westmount is a vibrant community in the Greater Toronto Area, offering excellent amenities, schools, and transportation options. This area is popular with families and professionals seeking a balanced lifestyle with access to urban conveniences and natural spaces.
Why Live in 1019 - WM Westmount
- •Convenient location in Oakville
- •Access to local shops and dining
- •Good public transit connections
- •Community parks and green spaces
- •Well-maintained neighbourhoods
Nearby Schools
Transit & Commuting
- •MiWay bus routes throughout the area
- •GO Transit stations within driving distance
- •Easy highway access to 401/403/QEW
- •Walking distance to local amenities
Parks & Amenities
- •Local parks and recreational facilities
- •Community centres
- •Shopping plazas nearby
- •Restaurants and cafes
Lifestyle & Community
1019 - WM Westmount offers a wonderful quality of life with a mix of residential charm and urban convenience. Residents enjoy easy access to schools, parks, and shopping, making it an ideal location for families and professionals alike.
2371 Calloway Drive, Oakville
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Monthly Cash Flow Breakdown
Note: These are estimates only. Actual figures may vary based on market conditions, property condition, and other factors. Consult with a financial advisor for personalized advice.

Joe's Thoughts
Honest perspective from 30+ years of GTA real estate experience
Competitive Pricing
At $600/sqft, this is priced below the area average. This could represent genuine value, but let's investigate why. In my experience, underpriced homes often have deferred maintenance, unfavourable layouts, or motivated sellers. I'll help you determine which it is.
Market Position
At 27 days on site, this property has had reasonable exposure. It hasn't sold immediately (which often indicates overpricing), but isn't languishing either. There's likely room for a 3-5% negotiation from asking price.
Detached Home Advantages
Detached homes in Oakville are increasingly scarce and valuable. You'll have no shared walls, full control over renovations, and typically stronger appreciation. Consider the lot size and potential for future additions or basement apartment income. Detached homes also offer the most flexibility for growing families.
Larger Home Realities
At 3,000 sqft, this is a substantial home. Budget approximately $400-600/month more for utilities compared to an average-sized home. Maintenance costs scale with size too - roof, HVAC, and cleaning all cost more. That said, space is a luxury that's hard to add later, and larger homes often have better resale in family-oriented neighbourhoods.
Excellent Flexibility
With 5 bedrooms, you have genuine flexibility. Beyond the master and kids' rooms, you can have a dedicated home office, guest room, hobby space, or even rental income potential. In today's work-from-home era, extra bedrooms add significant value. Properties with 5+ bedrooms are relatively rare in Oakville.
Bathroom Count Matters
With 5 bathrooms, morning routines are much smoother. Multiple bathrooms significantly improve daily livability and are a major selling point for resale. Buyers consistently pay more for adequate bathroom counts - this is a strong feature.

















































