16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
16927 Winston Churchill Boulevard
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50 photos

16927 Winston Churchill Boulevard

Rural Caledon, Caledon, ON
Listed 26 days ago
$4,500,000For Sale
$1,684,802Estimated value
4+1Bedrooms
3Bathrooms
2500-3000 sqftSize
25 (5 garage)Parking
1006 ft × 597 ftLot Size
DetachedProperty Type

16927 Winston Churchill Boulevard

Caledon, ON · Rural Caledon

Listed 26 days ago
Bedrooms4+1
Bathrooms3
Size2500-3000 sqft
Parking25 (5 garage)
Lot Size1006 ft × 597 ft
Property TypeDetached
$4,500,000
For Sale
MLS# W13224014
$1,684,802Estimated value

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About this home

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 a…

Features & Details

Property Type
Detached
Tax
$4,145 / 2026
Building Age
100+ years
Size
2500-3000 sqft
Lot Size
1006.41 x 597 Feet
Basement Info
Partially Finished, Partial Basement
Total Parking Spaces
25 (5 Garage)
Title
Residential Freehold
Property Style
2-Storey
Community
Rural Caledon
Municipality
Caledon
Construction
Brick, Wood
Cross Street
Grange/Winston Churchill
Front Door Facing
East
Local Amenities
Lake/Pond, Wooded/Treed
Lot Legal Description
PT LT 8, CON 6WHS DES AS PT 1, 43R30816 SAVE AND EXCEPT PART 2 ON EXPROPRIATION PLAN PR4554666 SUBJECT TO AN EASEMENT OVER PARTS 6, 7, 8, 9, 10 & 12 ON EXPROPRIATION PLAN PR4554666 AS IN PR4554666 SUBJECT TO AN EASEMENT OVER PARTS 1, 3, 4, 5, 7, 9, 10 & 11 ON EXPROPRIATION PLAN PR4554666 AS IN PR4554666 TOWN OF CALEDON (CONT)
Data Source
Toronto Regional Real Estate Board
Brokerage
ROYAL LEPAGE RCR REALTY
Listed On
Jun 01, 2026
Listing Expires On
Jun 01, 2027
Listing Updated On
Jun 02, 2026
Bedrooms
4+1
Bathrooms
3
Kitchens
1
Rooms
11
Bathroom Detail
2 Pcs on Main Level
Bathroom Detail
5 Pcs on Main Level
Bathroom Detail
5 Pcs on 2nd Level
Driveway
Private
Garage Type
Detached
Garage
5
Parking
25
Heating
Forced Air
Heat Source
Propane
Cooling
Wall Unit(s)
Sewer
Septic
Den / Family Room
Yes
Fireplace
Propane, Wood
Swimming Pool
Inground
Roof Material
Shingles
Foundation Type
Stone
Interior Features
In-Law Capability, Primary Bedroom - Main Floor, Guest Accommodations, Water Treatment, Generator - Partial

Listing History

Active26 days on marketCurrently viewingMLS #W13224014
Jun 1, 202626 days ago
Listed for Sale
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This is the only listing record currently available for this property.

Estimate History

Estimated value, last 24 months
Jul 2024 – Jun 2026
$1.72M
$1.6M
$1.48M
$1.36M
Jul
Dec
May
Oct
Mar
Jun

Automated estimate from Polsinello Predictive AI. Not an appraisal. Actual market value may differ.

Mortgage calculator

Estimated monthly payment
$21,953

Estimated payment. Does not include property tax, insurance, or condo fees.

Location & nearby

Rural Caledon Real Estate Market

Caledon · last 90 days
$1,107,500
Median sold price
-22.8%
Median price, year over year
45 days
Avg days on market
80
Homes sold (90 days)
15%
Sold above asking
83%
Sold below asking
$496–$620/ft²
Price per sq ft
Median price trend
Jun 2025 – Jun 2026
$1.49M
$1.29M
$1.09M
$0.88M
Jun
Sep
Dec
Mar
Jun

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(905) 830-9111