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Home · Buy · Caledon · 14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8+ 24 photos
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
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14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
Caledon · Rural Caledon
For Sale · Detached
⚡1 hour ago

14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8

Caledon · Rural Caledon
MLS® W14114964
$1,988,000
New listing2-StoreyFinished, Full basementAttached · 2-car garage · 6 driveway · 8 total parking
+1 moreWest exposure
4
Beds
3
Baths
8
Parking
3500-5000
Sq ft
31-50 yrs
Built
OverviewDetailsMarketLocationHistory

Overview

About this home

  • 4 bedrooms, 3 bathrooms, 3,716 sq ft above grade plus finished lower level (over 4,700 sq ft total)
  • 2.43-acre property backing onto protected conservation land with no rear neighbours
  • Heated saltwater pool with waterfall and large patio
  • Two-storey living room with vaulted ceiling and two-way wood-burning fireplace
  • Kitchen with Miele appliances (oversized fridge, built-in oven, cooktop, flush-mount hood) opening to sunken family room
  • Finished basement with rec room and bonus room
  • 8 parking spaces in insulated double garage with epoxy floor

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: 0 days
Property tax
$2,025 (2025)
Lot
232.35 × 416.18 Feet
Style
2-Storey
Heating
Forced Air
Cooling
Central Air
MLS®
W14114964

Details

Full details

Parking
GarageAttached
Driveway6
Garage spaces2
Total parking8
Parking featuresPrivate Double

Room dimensions

RoomLevelDimensionsFeatures
FoyerMain5.67 × 3.41Hardwood Floor, Double Closet, Vaulted Ceiling(s)
Dining RoomMain3.89 × 4.04Hardwood Floor, French Doors, Crown Moulding
Living RoomMain3.89 × 4.78Hardwood Floor, 2 Way Fireplace, Vaulted Ceiling(s)
KitchenMain3.67 × 4.6Hardwood Floor, Quartz Counter, Centre Island
BreakfastMain3.84 × 3.73Hardwood Floor, 2 Way Fireplace, Large Window
Family RoomMain5.82 × 5.82Broadloom, Sunken Room, W/O To Pool
LaundryMain2.53 × 1.68Tile Floor, W/O To Yard, Laundry Sink
Primary BedroomSecond6.41 × 5.83Broadloom, Sunken Room, His and Hers Closets
BedroomSecond3.99 × 3.63Broadloom, Closet, Window
BedroomSecond4.67 × 2.87Broadloom, Closet, Window
BedroomSecond4.83 × 2.93Broadloom, Closet, Window
RecreationBasement9.46 × 8.49Broadloom, Fireplace, Above Grade Window
Exercise RoomBasement7.71 × 4.09Broadloom, Above Grade Window, Recessed Lighting

Market · Renavu Intelligence

How this home fits the market

See comparables →
Asking price
$1,988,000
↑ +64.2%
vs. the area benchmark
Asking price is 64% above the area benchmark
Where this price sits against the typical 2-storey detached home in Rural Caledon.
Benchmark $1,211,000
$1,150,000 – $1,271,000Typical low – high
List price$1,988,000
Benchmark$1,211,000
Typical range$1,150,000 – $1,271,000
Asking price is 64% above the area benchmark
Where this price sits against the typical 2-storey detached home in Rural Caledon.

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$36,235
Legal · title · inspection$2,800
Closing costs$39,035
Down payment$397,600
Total cash to close$436,635
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 RE/MAX HALLMARK REALTY LTD. · MLS® W14114964

History

Property & sold history

Listing history
Date StartDate EndPriceStatusListing ID
2026-10-25—$1,988,000For SaleW14114964
🔒

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

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$1,988,000
MLS® W14114964
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 RE/MAX HALLMARK REALTY LTD.. 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 October 25, 2026.

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$1,988,000
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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.

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Comparables

Homes near 14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
Sold🔒 Sold:
bed bath parking
sq ft km
Detached
Address shown after sign-in
See what it sold for →
Sold🔒 Sold:
bed bath parking
sq ft km
Detached
Address shown after sign-in
See what it sold for →
Sold🔒 Sold:
bed bath parking
sq ft km
Detached
Address shown after sign-in
See what it sold for →
Sold🔒 Sold:
bed bath parking
sq ft km
Detached
Address shown after sign-in
See what it sold for →
Sold🔒 Sold:
bed bath parking
sq ft km
Detached
Address shown after sign-in
See what it sold for →
Sold🔒 Sold:
bed bath parking
sq ft km
Detached
Address shown after sign-in
See what it sold for →
🔒

8 sold homes nearby

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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.

Getting around

  • Mount Pleasant GO stationGO Transit · 11.5 km away
  • Highway 410 · exit 21Nearest on-ramp · 9.4 km away

Map

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

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 · 82 sales over 3 months
Buyer'sBalancedSeller's

Homes in Rural Caledon are taking around 45 days to sell, and going for about 95.7% of asking. There is usually room to negotiate.

Median sold · Rural Caledon
$1,220,000
▲ 28.4% year over year
Homes sold · October 2026
25
46 days on market avg
Sold vs asking · October 2026
95.5%
4.5% under asking · 25 sales — room to negotiate
Detached median · Caledon
$1,220,000
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.