14409 Winston Churchill Boulevard, Caledon, ON L7C 1S6
Rural Caledon, Caledon · Near Winston Churchill Blvd & WellingtonRd 42 · View map
About this home
A rare offering in Terra Cotta! Nestled among mature trees on a picturesque and private lot, this charming 4-bedroom home is located in one of Peel's most coveted rural communities. Combining the tranquility of country living with the convenience of nearby amenities, this is a property with remarkable long-term appeal and value. The home features a spacious kitchen, an updated washroom, renovated flooring, and fresh paint throughout, providing a comfortable space to enjoy from day one while offering the flexibility to personalize over time. Whether your plans include tasteful enhancements, a future addition, or the design and construction of a custom estate home, the possibilities are endless. Premium treed properties in this highly desirable location seldom become available. Surrounded by natural beauty and offering outstanding privacy, this is your chance to create a truly special country retreat tailored to your vision and lifestyle.
The home
- Type
- Bungalow
- Style
- Bungalow
- Square footage
- 1500-2000 sq ft
- Bedrooms
- 4
- Bathrooms
- 1
- Kitchens
- 1
- Rooms
- 10
- Basement
- None
- Lot size
- 156 x 290.2 ft
- Faces
- East
Ownership & fees
- Ownership
- Freehold
- Monthly condo fee
- None
- Security
- Alarm System, Carbon Monoxide Detectors, Smoke Detector, Security System
- Exterior
- Brick
Heating & cooling
- Heating fuel
- Electric
- Heating type
- Baseboard
- Air conditioning
- Window Unit(s)
- Fireplace
- Yes
Garage & parking
- Garage
- Detached
- Garage spaces
- 2
- Driveway spaces
- 10
- Total parking
- 12
- Parking features
- Private, Private Double, Front Yard Parking
Taxes & other
- Property taxes
- $4,753/yr
- Tax year
- 2026
- Occupancy
- Owner
- Possession
- 30-90, Flexible
- Cross street
- Winston Churchill Blvd & WellingtonRd 42
- Neighbourhood
- Rural Caledon
More
- Price per sq ft
- ~$685 (at 1,750 sq ft)
- Listed
- Jul 9, 2026 · 95 days ago
- MLS® number
- W13544076
No matching details. Ask Will instead
The home and its surroundings
- Auto Garage Door Remote
- Carpet Free
- Primary Bedroom - Main Floor
- Propane Tank
- Water Heater Owned
- Water Softener
- Water Purifier
- Water Treatment
- Greenbelt/Conservation
- Park
- Wooded/Treed
- School Bus Route
- Mortgage
- Property tax
- Maintenance fee
Cash needed to close
Estimates only, using Canadian semi-annual compounding, Ontario land transfer tax. Mortgage default insurance is added when you put down less than 20%. Your lender and lawyer will confirm exact numbers.
14409 Winston Churchill Boulevard, Caledon, ON L7C 1S6
Rural Caledon, Caledon · Near Winston Churchill Blvd & WellingtonRd 42
Get directionsWhat’s nearbySchools nearby
Open this tab to load nearby schools.
Your commute
Enter where you go every day to see real drive times:
Listing history for 14409 Winston Churchill Boulevard
See what this home and others at the same address were listed for, what they sold for, and how long it took.
Sold prices are for members. It’s free, takes a few seconds, and unlocks the sale history on every listing.
Frequently asked questions about 14409 Winston Churchill Boulevard
Answers come straight from this home’s MLS® listing.
How much is 14409 Winston Churchill Boulevard listed for, and what would it cost each month?
14409 Winston Churchill Boulevard is listed for $1,199,000. With 20% down ($239,800), the mortgage payment would be roughly $4,836 a month at 4.5% over 30 years. Add property tax and the estimate comes to about $5,233 a month, all in. That figure is an illustration, not a quote.
Is 14409 Winston Churchill Boulevard freehold or a condo, and is there a monthly fee?
14409 Winston Churchill Boulevard is a bungalow in Rural Caledon, Caledon. Ownership is freehold: you own the home and the lot. There is no monthly condo fee, so the roof, windows, driveway, snow and lawn are yours to look after.
How many bedrooms and bathrooms does 14409 Winston Churchill Boulevard have?
14409 Winston Churchill Boulevard has 4 bedrooms and 1 bathroom.
Does 14409 Winston Churchill Boulevard have a garage and parking?
Yes. The listing shows the garage as detached, with room for 2 cars. The driveway adds 10 spaces. In total the listing counts 12 parking spaces.
Does 14409 Winston Churchill Boulevard have a finished basement?
No. The listing shows no basement for this home.
What style of home is 14409 Winston Churchill Boulevard?
14409 Winston Churchill Boulevard is a bungalow. A bungalow has all of its main living space, including the bedrooms, on one floor, usually over a full basement.
How big is 14409 Winston Churchill Boulevard, and what is the lot size?
The listing puts the home between 1,500 and 2,000 sq ft. The board reports a range rather than an exact figure, and it usually leaves out the basement. The lot is listed as 156 x 290.2 ft.
How is 14409 Winston Churchill Boulevard heated and cooled?
Heating is baseboard (electric). Cooling is window unit(s).
What are the property taxes for 14409 Winston Churchill Boulevard?
Property taxes are $4,753 a year (2026), or about $396 a month.
Where is 14409 Winston Churchill Boulevard?
14409 Winston Churchill Boulevard is in the Rural Caledon community of Caledon. The nearest main intersection is Winston Churchill Blvd & WellingtonRd 42. The postal code is L7C 1S6.
How long has 14409 Winston Churchill Boulevard been on the market?
14409 Winston Churchill Boulevard was listed on July 9, 2026. It has been on the market for 95 days. It is an active listing (MLS® W13544076). Listings here update from the board through the day and come down once a home sells.
What are similar bungalows near 14409 Winston Churchill Boulevard asking?
Similar bungalow-style homes for sale nearby right now include 13946 Mclaughlin Road at $1,090,000 (3+3 bed), 15553 The Gore Road at $1,313,000 (3+2 bed) and 21 Birchview Drive at $1,329,000 (3+1 bed). These are asking prices, not sold prices. The Sold history tab shows what homes at this address went for.
What have homes at 14409 Winston Churchill Boulevard sold for?
Recent sales, leases and expired listings for this home and others at the same address are in the Sold history tab, with the price and date of each. It is free for members.
How do I book a showing at 14409 Winston Churchill Boulevard?
Pick a day and time with Book a Tour on this page. Tours are free, with no obligation, in person or by video. You can also call or text 647-619-2256.
Have a different question? Ask about this home and get an answer, usually within the hour.
Similar bungalows nearby
More bungalow-style homes for sale near Rural Caledon, picked by style, size and price.
Bungalow$1,090,00013946 Mclaughlin Road, Caledon3+3 bed · 2 bath · Rural CaledonCourtesy of: HOMELIFE/MIRACLE REALTY LTDView home →
Bungalow$1,313,00015553 The Gore Road, Caledon3+2 bed · 4 bath · Rural CaledonCourtesy of: CENTURY 21 PEOPLE`S CHOICE REALTY INC.View home →
Bungalow$1,329,00021 Birchview Drive, Caledon3+1 bed · 4 bath · Rural CaledonCourtesy of: RE/MAX HALLMARK YORK GROUP REALTY LTD.View home →Courtesy of: iCloud Realty Ltd.
PropTx MLS® assumes no responsibility for the accuracy of any information shown. The information provided herein must only be used by consumers that have a bona fide interest in the purchase, sale or lease of real estate and may not be used for any commercial purpose or any other purpose.
*Estimated monthly cost assumes 20% down, a 4.5% rate and a 30-year amortization, plus property tax. For illustration only.