$4,248,000 - 1399 WILLOWDOWN Road, Oakville
Detached for Sale in Oakville
New — Listed 6 days agoNeighbourhood: 1017 - SW Southwest
- MLS Number
- W13685756
- Property Type
- Detached
- Status
- active
- Days on Site
- 6
- Bedrooms
- 7
- Bathrooms
- 7
- Square Feet
- 3,500 - 3,999 sqft
- Neighbourhood
- Oakville
- Lot Size
- 13,939 sqft
- Listing Brokerage
- CENTURY 21 MILLER REAL ESTATE LTD.
Welcome to 1399 Willowdown Road, an exceptional custom residence inspired by Frank Lloyd Wright's iconic Prairie designs, nestled on a spectacular ravine lot with a picturesque creek in prestigious South Oakville. Offering over 6,800 sq. ft. of beautifully finished living space, this remarkable home features 5 bedrooms upstairs plus 2 additional bedrooms in the finished lower level. The main floor impresses with soaring 10' ceilings, wide-plank oak flooring, custom millwork and an open-concept layout. At its heart is a chef-inspired kitchen with an oversized island, quartz counters, JennAir Professional Series appliances, extensive cabinetry and a butler pantry, opening to the expansive great room and breakfast area. Enjoy seamless indoor-outdoor living from the covered lanai with a fireplace and skylights overlooking the ravine. The finished lower level is designed for entertaining, featuring a dedicated home theatre, billiards and recreation areas, exercise room, 2 bedrooms and a full bathroom. Additional highlights include Lutron lighting automation, remote-controlled blinds, built-in ceiling speakers, multi-camera security, illuminated stair treads, 9' upper-level ceilings and a double garage. Just steps from Coronation Park and Lake Ontario, and minutes to top schools, shopping, dining and GO Transit. A truly rare offering combining architectural distinction, exceptional space and ravine-side privacy.
Estimate your monthly payments for this property
Estimated Payment
$18,790.34/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 1017 - SW Southwest
1017 - SW Southwest 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 1017 - SW Southwest
- •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
1017 - SW Southwest 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.
1399 WILLOWDOWN Road, Oakville
Open in Google MapsUse the map controls to zoom, pan, and switch between map and satellite views. Drag to explore the neighbourhood.
Rental income estimator & ROI calculator
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
Premium Pricing
At $1214/sqft, this property is priced above the Oakville average of $950/sqft. I'd want to see upgraded finishes, premium location, or recent renovations to justify this price point. During our showing, I'll point out exactly what you're paying extra for.
Just Listed - Act Strategically
This property hit the market within the last week. In Oakville's current market, desirable homes often receive multiple offers within 5-7 days. If you're seriously interested, I recommend booking a showing immediately. However, never let urgency override due diligence - we'll still do proper inspections.
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 3,500 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 7 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 7 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.