16927 Winston Churchill Blvd, Caledon

Name: 16927 Winston Churchill Boulevard
SKU: W13224014
Price: 4200000 CAD
Availability: InStock

4 Bed, 2 Bath Detached Home in Caledon

About 16927 Winston Churchill Boulevard

A Victorian reimagined, complete with a secret English garden. Just outside Belfountain, on nearly 15 acres of Caledon countryside, it is steeped in character and completely its own. The main house holds four bedrooms and three bathrooms, anchored by a bright central kitchen with the family room close at hand, cozy with its own fireplace. A breakfast nook looks out over perennial gardens and the pool beyond, with a screened Muskoka room just around the corner. The living room, with a dramatic architectural staircase as its focal point, overlooks the gardens and pond. A home you fall deeper into with every room. Waking up to gardens and pond, the main floor primary wing is a true sanctuary. A spa-like five piece ensuite, marble throughout, with soaker tub and steam shower. Upstairs, three additional bedrooms and a lovely five piece bath. Outside, the property opens into something rare. A 40 foot rectangular pool at the heart of the grounds, with a pool house and al fresco dining zone built for summer entertaining. A spring-fed pond with fountain and trails winding throughout. Heritage barn ruins that carry their own romance. (A family wedding was once held there, and the potential remains.) Once featured on the Caledon Garden Tour, the gardens include a spectacular Rhododendron forest. The outbuildings are exceptional. A detached two-car garage for the everyday and a heated three-bay garage for hobbies, toys, and your car collection, with one bay currently fitted as a sculpture studio. The garden cottage, a gym today complete with bathroom plus kitchen and laundry hookups, converts easily into a private one-bedroom suite for in-laws, older kids, or guests wanting their own world. A garden tea house overlooking the spring-fed pond, perfect for yoga or meditation. Minutes from Belfountain, close to great schools, skiing, hiking trails, golf, equestrian, local shops and restaurants. This is a home that holds everything.

4 bedrooms, 2 bathrooms, about 2,500 sq ft, works out to roughly $1,680 per square foot. Chat with Zara if you'd like a deeper read on whether this detached fits your budget and timing.

Inside 16927 Winston Churchill Blvd

Every detail from the listing, in one place.

Type: Detached
Style: 2-Storey
Living space: 2500-3000 sq ftas stated on the listing
Lot size: 14.95 x 0.00 Acres
Parking: 25 spacesYes garage
Basement: Partially Finished, Partial Basement

Features & systems

Parking & garage

Garage: Yes
Parking spaces: 25

Interior

Basement: Partially Finished · Partial Basement

Exterior & construction

Pool: Yes

Lot & land

Lot dimensions: 14.95 x 0.00 Acres
Lot size (sqft): 0

Listing & possession

Property style: 2-Storey
Property class: Detached

16927 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® W13224014−$300,000 (6.7%)$4,200,000
Jun 1, 2026For saleListedThis listingMLS® W13224014$4,500,000

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

What's it worth?

How 16927 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 524 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: $1,022,500
Average sold price: $1,128,570
Average days on market: 40
Homes sold: 308

Closed sales on the TRREB MLS®.

Full Caledon market report

Market pulse · Caledon

Caledon market

Median sold price$1,022,500Last 90 days
Average days on market40Homes sold in about 40 days on average.
Sale-to-list ratio96.3%On average, homes sold below asking.
Active listings578Homes for sale here right now.
Median vs prior 90 days−4.4%Compared with Apr 26 – Jul 25, 2026: prices down.

Based on 308 sales from Jul 25 – Oct 23, 2026 (223 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 home16927 Winston Churchill Boulevard 4 bd · 2 ba · 2,500 sqft	$4,200,000asking	$1,680	—	—
108 Hemlock Street 3 bd · 1 ba · 1,500 sqft
76 Birchview Crescent 3 bd · 1 ba · 1,500 sqft
41 Daisy Meadow Crescent 4 bd · 4 ba · 3,000 sqft
92 Senator Way 3 bd · 2 ba · 1,500 sqft
26 Davis Drive 3 bd · 1 ba · 1,100 sqft
55 William Crisp Drive 5 bd · 5 ba · 3,500 sqft

108 Hemlock Street
3 bd · 1 ba · 1,500 sqft
76 Birchview Crescent
3 bd · 1 ba · 1,500 sqft
41 Daisy Meadow Crescent
4 bd · 4 ba · 3,000 sqft
92 Senator Way
3 bd · 2 ba · 1,500 sqft
26 Davis Drive
3 bd · 1 ba · 1,100 sqft
55 William Crisp Drive
5 bd · 5 ba · 3,500 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 16927 Winston Churchill Blvd. Typical times without traffic delays; transit times aren't available yet.

Costs, Mortgage & Rental Return for 16927 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: $20,633; 20% down · 25 years · 5.5% assumed
Property tax: $2,310; 0.66% mill rate · ON
Total per month: $22,943; 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

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Down payment

Rate (%)

Years

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

Affordability calculator

Estimated monthly payment

$20,633

/mo

based on the purchase price of $4,200,000

Down payment20%

$840,000 cash

Amortization25 yr

$3,360,000 financed

Rate5.50%

$2,830,002 total interest

Principal54%$3,360,000

Interest46%$2,830,002

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 16927 Winston Churchill Blvd

How much is 16927 Winston Churchill Blvd listed for?

16927 Winston Churchill Blvd is listed at $4,200,000 (MLS® W13224014). Summitly updates the price as soon as the MLS® record changes.

Is $4,200,000 a good price for 16927 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 16927 Winston Churchill Blvd changed?

Yes — it was first listed at $4,500,000 and is now $4,200,000, a drop of $300,000 (6.7%).

How many bedrooms and bathrooms does 16927 Winston Churchill Blvd have?

16927 Winston Churchill Blvd has 4 bedrooms and 2 bathrooms, with about 2,500–3,000 square feet of living space. It is a detached home in Caledon.

How much would the monthly mortgage be on 16927 Winston Churchill Blvd?

About $20,633 a month — principal and interest on $4,200,000 with 20% down ($840,000), 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 16927 Winston Churchill Blvd compare with other homes in Caledon?

Its asking price of $4,200,000 is about 311% above the median sold price in Caledon over the last 90 days, $1,022,500, across 308 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 16927 Winston Churchill Blvd been sold before?

Summitly has no earlier MLS® sale or lease of 16927 Winston Churchill Blvd on record from the last two years. Older records aren't shown under TRREB rules.

Where is 16927 Winston Churchill Blvd?

16927 Winston Churchill Blvd is in Caledon, ON. Schools, transit, parks and shops nearby are under Location & lifestyle on this page.

How long has 16927 Winston Churchill Blvd been on the market?

144 days — 16927 Winston Churchill Blvd was listed on June 1, 2026.

What is the price per square foot of 16927 Winston Churchill Blvd?

About $1,400 to $1,680 per square foot: the asking price of $4,200,000 over the 2,500–3,000 sq ft the listing gives as its size range.

Does 16927 Winston Churchill Blvd have parking or a garage?

Yes — the listing gives 25 parking spaces. Garage: Yes.

Does 16927 Winston Churchill Blvd have a basement, and is it finished?

The listing describes the basement as: Partially Finished, Partial Basement.

16927 Winston Churchill Blvd, Caledon

What you should know

4 Bed, 2 Bath Detached Home in Caledon

About 16927 Winston Churchill Boulevard

Inside 16927 Winston Churchill Blvd

Features & systems

16927 Winston Churchill Blvd Price & Sale History

How 16927 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 16927 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 16927 Winston Churchill Blvd, Caledon in person

Similar homes for sale nearby in Caledon

Explore More Detached Homes in Caledon

4 Bed, 2 Bath Detached Home in Caledon

About 16927 Winston Churchill Boulevard

Inside 16927 Winston Churchill Blvd

Features & systems

16927 Winston Churchill Blvd Price & Sale History

How 16927 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 16927 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 16927 Winston Churchill Blvd, Caledon in person

Questions About 16927 Winston Churchill Blvd

How much is 16927 Winston Churchill Blvd listed for?

Is $4,200,000 a good price for 16927 Winston Churchill Blvd?

Has the price of 16927 Winston Churchill Blvd changed?

How many bedrooms and bathrooms does 16927 Winston Churchill Blvd have?

How much would the monthly mortgage be on 16927 Winston Churchill Blvd?

How does 16927 Winston Churchill Blvd compare with other homes in Caledon?

Has 16927 Winston Churchill Blvd been sold before?

Where is 16927 Winston Churchill Blvd?

How long has 16927 Winston Churchill Blvd been on the market?

What is the price per square foot of 16927 Winston Churchill Blvd?

Does 16927 Winston Churchill Blvd have parking or a garage?

Does 16927 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 16927 Winston Churchill Blvd

How much is 16927 Winston Churchill Blvd listed for?

Is $4,200,000 a good price for 16927 Winston Churchill Blvd?

Has the price of 16927 Winston Churchill Blvd changed?

How many bedrooms and bathrooms does 16927 Winston Churchill Blvd have?

How much would the monthly mortgage be on 16927 Winston Churchill Blvd?

How does 16927 Winston Churchill Blvd compare with other homes in Caledon?

Has 16927 Winston Churchill Blvd been sold before?

Where is 16927 Winston Churchill Blvd?

How long has 16927 Winston Churchill Blvd been on the market?

What is the price per square foot of 16927 Winston Churchill Blvd?

Does 16927 Winston Churchill Blvd have parking or a garage?

Does 16927 Winston Churchill Blvd have a basement, and is it finished?