14409 Winston Churchill Blvd, Caledon

Name: 14409 Winston Churchill Boulevard
SKU: W13544076
Price: 1170000 CAD
Availability: InStock

4 Bed, 1 Bath Detached Home in Caledon

About 14409 Winston Churchill Boulevard

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.

4 bedrooms, 1 bathroom, about 1,500 sq ft, works out to roughly $780 per square foot. Chat with Zara if you'd like a deeper read on whether this detached fits your budget and timing.

Inside 14409 Winston Churchill Blvd

Every detail from the listing, in one place.

Type: Detached
Style: Bungalow
Living space: 1500-2000 sq ftas stated on the listing
Parking: 12 spacesYes garage
Basement: None

Features & systems

Parking & garage

Garage: Yes
Parking spaces: 12

Interior

Basement: None

Lot & land

Lot size (sqft): 0

Listing & possession

Property style: Bungalow
Property class: Detached

14409 Winston Churchill Blvd Price & Sale History

Earlier listings of this property, list-price changes, and the most recent annual property tax on the listing.

—ReducedPrice reducedThis listingMLS® W13544076−$29,000 (2.4%)$1,170,000
Jul 9, 2026For saleListedThis listingMLS® W13544076$1,199,000

Sourced from MLS®. Includes earlier listings of this property on record.

What's it worth?

How 14409 Winston Churchill Blvd Compares to the Caledon Market

Zara compares it with recent sales of similar homes nearby. It's a guide, not an appraisal.

Zara’s estimate

Well Above Market· based on 540 recent sales

Value your own home →How accurate are Zara’s estimates?

Summitly estimate, not from TRREB, the MLS® or the listing brokerage. Not an appraisal. How it works

Caledon market, last 90 days

Median sold price: $1,015,000
Average sold price: $1,158,779
Average days on market: 42
Homes sold: 326

Closed sales on the TRREB MLS®.

Full Caledon market report

Market pulse · Caledon

Caledon market

Median sold price$1,015,000Last 90 days
Average days on market42Homes sold in about 42 days on average.
Sale-to-list ratio96.1%On average, homes sold below asking.
Active listings541Homes for sale here right now.
Median vs prior 90 days−5.1%Compared with May 12 – Aug 10, 2026: prices down.

Based on 326 sales from Aug 10 – Nov 8, 2026 (240 in the prior 90 days). Aggregate MLS® figures for closed sales; individual sold prices are shown only to signed-in members.

Recently sold nearby in Caledon

Sold prices are shown free to signed-in members, as board rules require.

6 nearby sales vs. this home

Closed sales from MLS®, compared with this home's asking price.

See what these homes actually sold for

Free with a Summitly account. Sign in once and sold prices unlock across the site.

Home	Sold price	$ / sqft	% of asking	Sold
This home14409 Winston Churchill Boulevard 4 bd · 1 ba · 1,500 sqft	$1,170,000asking	$780	—	—
3045 Highpoint Side Road 4 bd · 4 ba · 3,500 sqft
30 Albert Spencer Avenue 4 bd · 6 ba · 3,000 sqft
19817 Main Street 4 bd · 2 ba · 1,500 sqft
7 Proctor Avenue 4 bd · 5 ba · 3,500 sqft
18161 Heart Lake Road 3 bd · 2 ba · 2,500 sqft
3 Bowes Court 4 bd · 3 ba · 2,500 sqft

3045 Highpoint Side Road
4 bd · 4 ba · 3,500 sqft
30 Albert Spencer Avenue
4 bd · 6 ba · 3,000 sqft
19817 Main Street
4 bd · 2 ba · 1,500 sqft
7 Proctor Avenue
4 bd · 5 ba · 3,500 sqft
18161 Heart Lake Road
3 bd · 2 ba · 2,500 sqft
3 Bowes Court
4 bd · 3 ba · 2,500 sqft

Living in Caledon: Location & Amenities

Transit, schools, parks and everyday places near this home. Select any place to open it on Google Maps.

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How long is your commute?

From 14409 Winston Churchill Blvd. Typical times without traffic delays; transit times aren't available yet.

Costs, Mortgage & Rental Return for 14409 Winston Churchill Blvd

What it could cost each month, today's rates from our mortgage partner, and what it could return as a rental.

Mortgage: $5,748; 20% down · 25 years · 5.5% assumed
Property tax: $644; 0.66% mill rate · ON
Total per month: $6,392; Before utilities, insurance and fees

Figures are Summitly estimates for illustration only — not from TRREB or the MLS® feed, and not a mortgage approval, appraisal, or financial advice.

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Monthly cost

Enter a rate to see the monthly cost

Down payment

Rate (%)

Years

An estimate, not a quote. Utilities and insurance are extra.

Affordability calculator

Estimated monthly payment

$5,748

/mo

based on the purchase price of $1,170,000

Down payment20%

$234,000 cash

Amortization25 yr

$936,000 financed

Rate5.50%

$788,358 total interest

Principal54%$936,000

Interest46%$788,358

20% down · 25-yr amortization · 5.50% rate. Principal & interest only — taxes, condo fees, and insurance not included.

Want rate-drop alerts and a saved shortlist?

Figures are Summitly estimates for illustration only — not from TRREB or the MLS® feed, and not a mortgage approval, appraisal, or financial advice.

Rental income potential

Est. monthly rent

low–high

Gross yield

rent × 12 ÷ price

Cap rate (est.)

net of tax + fees

Summitly AI estimate for discussion only — not from TRREB or the MLS® feed, and not an appraisal or investment advice. Yield and cap rate are derived from the estimated rent versus the asking price.

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Questions About 14409 Winston Churchill Blvd

How much is 14409 Winston Churchill Blvd listed for?

14409 Winston Churchill Blvd is listed at $1,170,000 (MLS® W13544076). Summitly updates the price as soon as the MLS® record changes.

Is $1,170,000 a good price for 14409 Winston Churchill Blvd?

Summitly rates it Well Above Market: the asking price is 15% or more above Zara's estimate, an estimate built from recent sales in Caledon. The rating is an automated opinion, not an appraisal; "What's it worth?" on this page shows how it is worked out. See Zara's estimate

Has the price of 14409 Winston Churchill Blvd changed?

Yes — it was first listed at $1,199,000 and is now $1,170,000, a drop of $29,000 (2.4%).

How many bedrooms and bathrooms does 14409 Winston Churchill Blvd have?

14409 Winston Churchill Blvd has 4 bedrooms and 1 bathroom, with about 1,500–2,000 square feet of living space. It is a detached home in Caledon.

How much would the monthly mortgage be on 14409 Winston Churchill Blvd?

About $5,748 a month — principal and interest on $1,170,000 with 20% down ($234,000), a 25-year amortization and an assumed 5.5% interest rate. The mortgage calculator on this page lets you change the down payment, amortization and rate.

How does 14409 Winston Churchill Blvd compare with other homes in Caledon?

Its asking price of $1,170,000 is about 15% above the median sold price in Caledon over the last 90 days, $1,015,000, across 326 closed sales on the TRREB MLS®. A city median mixes every type and size of home, so the comparable sales on this page are the closer guide.

Has 14409 Winston Churchill Blvd been sold before?

Summitly has no earlier MLS® sale or lease of 14409 Winston Churchill Blvd on record from the last two years. Older records aren't shown under TRREB rules.

Where is 14409 Winston Churchill Blvd?

14409 Winston Churchill Blvd is in Caledon, ON. Schools, transit, parks and shops nearby are under Location & lifestyle on this page.

How long has 14409 Winston Churchill Blvd been on the market?

122 days — 14409 Winston Churchill Blvd was listed on July 9, 2026.

What is the price per square foot of 14409 Winston Churchill Blvd?

About $585 to $780 per square foot: the asking price of $1,170,000 over the 1,500–2,000 sq ft the listing gives as its size range.

Does 14409 Winston Churchill Blvd have parking or a garage?

Yes — the listing gives 12 parking spaces. Garage: Yes.

Does 14409 Winston Churchill Blvd have a basement, and is it finished?

The listing says 14409 Winston Churchill Blvd has no basement.

14409 Winston Churchill Blvd, Caledon

What you should know

4 Bed, 1 Bath Detached Home in Caledon

About 14409 Winston Churchill Boulevard

Inside 14409 Winston Churchill Blvd

Features & systems

14409 Winston Churchill Blvd Price & Sale History

How 14409 Winston Churchill Blvd Compares to the Caledon Market

Caledon market, last 90 days

Recently sold nearby in Caledon

Living in Caledon: Location & Amenities

How long is your commute?

Costs, Mortgage & Rental Return for 14409 Winston Churchill Blvd

Monthly cost of owning

Mortgage payments

Monthly cost

Rental income potential

Own a home on Winston Churchill Boulevard? See what yours is worth

Zara, any time

A licensed local agent

See 14409 Winston Churchill Blvd, Caledon in person

Similar homes for sale nearby in Caledon

Explore More Detached Homes in Caledon

4 Bed, 1 Bath Detached Home in Caledon

About 14409 Winston Churchill Boulevard

Inside 14409 Winston Churchill Blvd

Features & systems

14409 Winston Churchill Blvd Price & Sale History

How 14409 Winston Churchill Blvd Compares to the Caledon Market

Caledon market, last 90 days

Market pulse · Caledon

Recently sold nearby in Caledon

Living in Caledon: Location & Amenities

How long is your commute?

Costs, Mortgage & Rental Return for 14409 Winston Churchill Blvd

Monthly cost of owning

Mortgage payments

Monthly cost

Rental income potential

Own a home on Winston Churchill Boulevard? See what yours is worth

Zara, any time

A licensed local agent

See 14409 Winston Churchill Blvd, Caledon in person

Questions About 14409 Winston Churchill Blvd

How much is 14409 Winston Churchill Blvd listed for?

Is $1,170,000 a good price for 14409 Winston Churchill Blvd?

Has the price of 14409 Winston Churchill Blvd changed?

How many bedrooms and bathrooms does 14409 Winston Churchill Blvd have?

How much would the monthly mortgage be on 14409 Winston Churchill Blvd?

How does 14409 Winston Churchill Blvd compare with other homes in Caledon?

Has 14409 Winston Churchill Blvd been sold before?

Where is 14409 Winston Churchill Blvd?

How long has 14409 Winston Churchill Blvd been on the market?

What is the price per square foot of 14409 Winston Churchill Blvd?

Does 14409 Winston Churchill Blvd have parking or a garage?

Does 14409 Winston Churchill Blvd have a basement, and is it finished?

Similar homes for sale nearby in Caledon

Explore More Detached Homes in Caledon

Market pulse · Caledon

Questions About 14409 Winston Churchill Blvd

How much is 14409 Winston Churchill Blvd listed for?

Is $1,170,000 a good price for 14409 Winston Churchill Blvd?

Has the price of 14409 Winston Churchill Blvd changed?

How many bedrooms and bathrooms does 14409 Winston Churchill Blvd have?

How much would the monthly mortgage be on 14409 Winston Churchill Blvd?

How does 14409 Winston Churchill Blvd compare with other homes in Caledon?

Has 14409 Winston Churchill Blvd been sold before?

Where is 14409 Winston Churchill Blvd?

How long has 14409 Winston Churchill Blvd been on the market?

What is the price per square foot of 14409 Winston Churchill Blvd?

Does 14409 Winston Churchill Blvd have parking or a garage?

Does 14409 Winston Churchill Blvd have a basement, and is it finished?