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Home · Buy · Caledon · 16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
Caledon · Rural Caledon
For Sale · Detached
◷3 months ago

16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9

Caledon · Rural Caledon
MLS® W13224014
$4,200,000
▶ Virtual Tour
▾ PRICE CHANGE
2-StoreyPartially Finished, Partial Basement basementDetached · 5-car garage · 20 driveway · 25 total parkingEast exposure
4 + 1
Beds
3
Baths
25
Parking
2500-3000
Sq ft
100+ yrs
Built
OverviewDetailsMarketLocationHistory

Overview

About this home

  • 4 + 1 bedrooms, 3 bathrooms on 2500-3000 sq ft
  • Nearly 15 acres in Caledon countryside near Belfountain
  • Main floor primary suite with five-piece ensuite including soaker tub and steam shower
  • 40-foot rectangular pool, pool house, spring-fed pond with fountain, and garden trails
  • Detached 25-car garage plus heated three-bay garage with one bay set up as sculpture studio
  • Garden cottage currently used as gym with bathroom, kitchen, and laundry hookups; converts to 4 + 1-bedroom guest suite
  • 25 parking spaces available

Key points are generated by Renavu from the listing description — not from, provided by, or endorsed by TRREB or PropTx.

Property details

Days on market
🔒Sign in to view
Days on site: 104 days
Property tax
$4,145.22 (2026)
Lot
1006.41 × 597 Feet
Style
2-Storey
Rooms
8
Heating
Forced Air
Cooling
Wall Unit(s)
MLS®
W13224014

Details

Full details

Parking
GarageDetached
Driveway20
Garage spaces5
Total parking25
Parking featuresPrivate

Market · Renavu Intelligence

How this home fits the market

Luxury homes are valued one at a time
Ask The Renavu Team for a valuation of this home.

The Renavu Estimate and the figures in this section are produced by Renavu using our own analysis — not statistics from, provided by, or endorsed by TRREB or PropTx. Underlying property data is provided through TRREB/PropTx and is deemed reliable but not guaranteed accurate. Renavu Estimate is our data-driven opinion of value and a market reference — not this home's exact value.

Comparables

Gathering recent comparable sales nearby…

Run the numbers

True cost to close
What you actually need in cash — land transfer tax, closing costs, and your down payment.
Purchase price
$
Down payment · 20.0%
$
Down:or type any amount above
Homes over $1.5M require a minimum 20% down payment.
Legal fees
$
Title insurance
$
Home inspection
$
Ontario land transfer tax$91,475
Legal · title · inspection$2,800
Closing costs$94,275
Down payment$840,000
Total cash to close$934,275
Estimates only, not legal or tax advice. Ontario LTT rates 2025; City of Toronto MLTT applies inside Toronto (incl. Scarborough, North York, Etobicoke, York, East York). Durham and Markham buyers pay no municipal LTT.

Location

Listed by ROYAL LEPAGE RCR REALTY · MLS® W13224014

History

Property & sold history

Listing history
Date StartDate EndPriceStatusListing ID
2026-09-08—$4,200,000 ▼Price cutW13224014
0000-00-00—(Sign-in required)ListedW13224014
🔒

Earlier listings and sold prices for this address are protected under TRREB rules — a free account unlocks them.

Sign in free to unlock the history
$4,200,000
MLS® W13224014
Homes in Rural Caledon are selling at 96% of asking.

That's from 25 recent sales nearby. Want to know what it means for yours?

Get my Rural Caledon valuation
Call The Renavu Team
Shan Perinpanathan
Shan Perinpanathan
Real Estate Broker, ABR, SRS
416.655.4040
Pam Thiyagarajah
Pam Thiyagarajah
Sales Representative
416.436.0546
Ragu Rajaguru
Ragu Rajaguru
Real Estate Broker
416.712.2006

Price and status changes on this home only. No newsletter, and no call unless you ask for one. Unsubscribe from any email. The Renavu Team, Royal LePage Ignite Realty, Brokerage.

One team. No spam. We reach out once — when you ask.

Listing courtesy of ROYAL LEPAGE RCR REALTY. Presented by Royal LePage Ignite Realty, Brokerage. Data provided by TRREB — deemed reliable but not guaranteed; for consumers' personal, non-commercial use. Listing information last updated September 10, 2026.

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$4,200,000
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© 2026 The Renavu Team · Royal LePage Ignite Realty, Brokerage · Privacy · Terms · · We don't sell your data.

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.

Listing data is provided by the Toronto Regional Real Estate Board (TRREB) through PropTx and is deemed reliable but is not guaranteed accurate by PropTx. The trademarks REALTOR®, REALTORS®, and the REALTOR® logo are controlled by The Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by CREA and identify the quality of services provided by real estate professionals who are members of CREA. IDX information is for consumers' personal, non-commercial use.

Neighbourhood market

The Rural Caledon market

How homes are selling here right now — sold data for October 2026.

Buyer's marketAll home types in Rural Caledon · 89 sales over 3 months
Buyer'sBalancedSeller's

Homes in Rural Caledon are taking around 45 days to sell, and going for about 95.5% of asking. There is usually room to negotiate.

Median sold · Rural Caledon
$1,180,000
▲ 24.2% year over year
Homes sold · October 2026
32
45 days on market avg
Sold vs asking · October 2026
95.1%
4.9% under asking · 32 sales — room to negotiate
Detached median · Caledon
$1,200,000
See the full Caledon market report →

These figures are produced by Renavu — they are not official statistics from, provided by, or endorsed by TRREB or PropTx, and are deemed reliable but not guaranteed accurate. Neighbourhood figures with only a handful of sales are held back so no single sale is identifiable.

Getting around

  • Acton GO stationGO Transit · 15.5 km away
  • Highway 410 · exit 21Nearest on-ramp · 15.1 km away

Map

Directions → · Places © OpenStreetMap contributors. Straight-line distances.

Similar homes for sale

Comparable homes on the market near Caledon · Rural Caledon — same kind of property, similar size and price.

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See everything for sale nearby

Comparables

Homes near 16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
19977 Kennedy Road, Caledon, ON L7K 1Z2
⚡ NEW
$1,499,900
19977 Kennedy RoadCaledon, ON L7K 1Z2
Caledon · Rural Caledon
4 bed3 bath10 parking2500–3000 sq ft
⚡Yesterday
Renavu EstimateHigh
16% above our estimate
Estimated value: $1,296,000
MLS® W14129792HOMELIFE MAPLE LEAF REALTY LTD.
3 Cliffcrest Court, Caledon, ON L7C 1C1
⚡ NEW
$1,499,000
3 Cliffcrest CourtCaledon, ON L7C 1C1
Caledon · Rural Caledon
4 bed5 bath8 parking2500–3000 sq ft
⚡Yesterday
Renavu EstimateMedium
14% above our estimate
Estimated value: $1,316,000
MLS® W14127396THE REALTY FIRM INC.
7 Proctor Avenue, Caledon, ON L7E 4E7
$2,595,000
7 Proctor AvenueCaledon, ON L7E 4E7
Caledon · Rural Caledon
4 + 1 bed6 bath10 parking3500–5000 sq ft
◷1 month ago
MLS® W13814062ROYAL LEPAGE RCR REALTY
47 Brookwater Crescent, Caledon, ON L7C 4A4
$1,249,900
47 Brookwater CrescentCaledon, ON L7C 4A4
Caledon · Rural Caledon
4 bed4 bath4 parking2500–3000 sq ft
◷5 days ago
Renavu EstimateLow
18% above our estimate
Estimated value: $1,063,000
MLS® W14114852LIST N SOLD REALTY CORP.
18101 Shaws Creek Road, Caledon, ON L7K 0E8
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5 + 1 bed5 bath11 parking3000–3500 sq ft
◷3 days ago
MLS® W14120446SOTHEBY'S INTERNATIONAL REALTY CANADA
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◷1 week ago
Renavu EstimateHigh
13% above our estimate
Estimated value: $1,286,000
MLS® W14110734RE/MAX REALTY SERVICES INC.

The comparables and the analysis shown here are produced by Renavu using our own analysis — not statistics from, provided by, or endorsed by TRREB or PropTx. Underlying property data is provided through TRREB/PropTx and is deemed reliable but not guaranteed accurate.