366 Winston Churchill Boulevard, Oakville

Price: $1,520,000

3 bedrooms, 3 bathrooms

1,500 - 1,999 sqft

Property Type: Detached

MLS#: W13241874

A Warm Family Home with Ravine Views in Southeast Oakville!***Welcome to this inviting 3+1 bedroom, 3 bathroom home, built on a solid foundation with a thoughtful layout designed for comfortable family living. Large picture windows in the living room frame a wow-factor view of the treed backyard, filling the main level with natural light. The family room flows to an upper deck - perfect for morning coffee or private evening entertaining - while the lower level offers a media room with over 7 ft ceilings and a walkout to a serene, natural backyard.***With solid bones throughout, the home is ready to enjoy today, or serves as the ideal canvas for your customization and modernization plans.***All of this sits on a rare 100 x 177 ft ravine lot surrounded by mature trees, delivering natural privacy and a country-like setting in one of Oakville's most sought-after neighbourhoods. You're steps from Lakeshore Road, a short walk to Lake Ontario, and minutes from waterfront parks, trails, and Joshua Creek's ravine walks. Vibrant downtown Oakville is just 5 scenic kilometres away, with excellent schools, the Southeast Sports Field, easy highway access, and the Clarkson GO station nearby.***If you've been waiting for a unique home in Oakville, this is your chance.

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$1,520,000 - 366 Winston Churchill Boulevard, Oakville

Detached for Sale in Oakville

32 days on market

Neighbourhood: 1006 - FD Ford

3Beds
3Baths
1,500 - 1,999Sq Ft
Detached
Property Details
MLS Number
W13241874
Property Type
Detached
Status
active
Days on Site
32
Bedrooms
3
Bathrooms
3
Square Feet
1,500 - 1,999 sqft
Neighbourhood
Oakville
Listing Brokerage
RE/MAX REALTY ENTERPRISES INC.
Description

A Warm Family Home with Ravine Views in Southeast Oakville!***Welcome to this inviting 3+1 bedroom, 3 bathroom home, built on a solid foundation with a thoughtful layout designed for comfortable family living. Large picture windows in the living room frame a wow-factor view of the treed backyard, filling the main level with natural light. The family room flows to an upper deck - perfect for morning coffee or private evening entertaining - while the lower level offers a media room with over 7 ft ceilings and a walkout to a serene, natural backyard.***With solid bones throughout, the home is ready to enjoy today, or serves as the ideal canvas for your customization and modernization plans.***All of this sits on a rare 100 x 177 ft ravine lot surrounded by mature trees, delivering natural privacy and a country-like setting in one of Oakville's most sought-after neighbourhoods. You're steps from Lakeshore Road, a short walk to Lake Ontario, and minutes from waterfront parks, trails, and Joshua Creek's ravine walks. Vibrant downtown Oakville is just 5 scenic kilometres away, with excellent schools, the Southeast Sports Field, easy highway access, and the Clarkson GO station nearby.***If you've been waiting for a unique home in Oakville, this is your chance.

Mortgage Calculator

Estimate your monthly payments for this property

Estimated Payment

$6,723.47/mo

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5-yr fixed avg.

Principal: $1,216,000Interest: $801,042
Mortgage Amount$1,216,000
Total Interest$801,042
Est. Property Tax$1,077/mo
Total Cost$2,017,042

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.

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Neighbourhood Guide: 1006 - FD Ford

Discover 1006 - FD Ford

1006 - FD Ford 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 1006 - FD Ford

  • Convenient location in Oakville
  • Access to local shops and dining
  • Good public transit connections
  • Community parks and green spaces
  • Well-maintained neighbourhoods

Nearby Schools

Oakville Trafalgar High SchoolPublic High School
Iroquois Ridge High SchoolPublic High School
Holy Trinity Catholic Secondary SchoolCatholic High School
Abbey Park High SchoolPublic High School

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

1006 - FD Ford 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.

70
Walk Score
Varies
Price Range

366 Winston Churchill Boulevard, Oakville

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Investor Analysis

Rental income estimator & ROI calculator

Estimated Monthly Rent
$2,800/mo
Range: $2,380 - $3,220
Cap Rate (ROI)
1.1%
Below Average

Monthly Cash Flow Breakdown

Rental Income+$2,800
Maintenance Fees-$0
Property Tax (est.)-$1,077
Insurance (est.)-$317
Net Cash Flow+$1,406

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 Battaglia - Top Real Estate Agent in Mississauga, REMAX Realty Specialists

Joe's Thoughts

Honest perspective from 30+ years of GTA real estate experience

Fair Market Value

At $1013/sqft, this property is priced in line with current Oakville market conditions. The pricing suggests the seller has done their homework. We may have modest room for negotiation, typically 2-4% in today's market.

Market Position

At 32 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.

Starter Home Potential

3 bedrooms works well for couples planning families or small families with one child. Consider whether you might outgrow the space in 5-7 years. If so, factor in potential moving costs when making your decision. Alternatively, some buyers convert a bedroom to an office and make it work long-term.

Bathroom Count Matters

With 3 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.

Oakville Premium

Oakville commands premium prices for good reasons: top-rated schools, waterfront access, charming downtown, and affluent community. Homes here hold value exceptionally well during market corrections. The trade-off is higher property taxes and home prices. If schools and lifestyle are priorities, Oakville delivers.

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    366 Winston Churchill Boulevard | $1,520,000 | Battaglia Team