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16927 Winston Churchill Boulevard
Rural Caledon Caledon L7K 1H9

$4,500,000
Residential Freehold beds: 4+1 baths: 3.0

Main Photo: 16927 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W13224014
Photo 1: 16927 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W13224014
Photo 2: 16927 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W13224014
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Status:
Active
Prop. Type:
Residential Freehold
MLS® Num:
W13224014
Bedrooms:
4+1
Bathrooms:
3
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.
Property Type:
Residential Freehold
Property Sub Type:
Detached
Home Style:
2-Storey
Approx. Age:
100+
Total Approx Floor Area:
2500-3000
Lot Size:
10-24.99
Lot Depth:
597'
Lot Frontage:
1006'5"
Lot Shape:
Rectangular
Lot Details:
14.95 x 0.00 Acres
Direction Faces:
East
Bedrooms:
4+1
Bathrooms:
3.0
Water supply:
Well
Kitchens:
2
Kitchens in Basement:
1
Bedrooms Above Grade:
4
Bedrooms Below Grade:
1
Kitchens Above Grade:
1
# Main Level Bedrooms:
0
# Main Level Bathrooms:
0
Rooms Above Grade:
11
Rooms:
8
Heating type:
Forced Air
Heating Fuel:
Propane
Fireplaces:
2
Foundation:
Stone
Roof:
Shingles
Basement:
Partially Finished, Partial Basement
Fireplace Features:
Propane, Wood
Fireplace/Stove:
Yes
Garage:
Detached
Garage Spaces:
5.0
Other Structures:
Workshop, Storage, Additional Garage(s), Out Buildings
Parking Features:
Private
Parking Spaces:
20
Total Parking Spaces:
25.0
Family Room:
Yes
Possession Details:
TBD
Pool:
Inground
Link:
No
HST Applicable To Sale Price:
Included In
Taxes:
$4,145.22 / 2026
Assessment:
$- / -
Peel
Caledon
Rural Caledon
Lake/Pond, Wooded/Treed
In-Law Capability, Primary Bedroom - Main Floor, Guest Accommodations, Water Treatment, Generator - Partial
Propane tank.
All appliances, electrical light fixtures, and window coverings. UV system, water softener. Pool accessories, pool fridge and pool sound system. EV charger.
Upstairs washer/dryer. Basement Fridge. Sculptures, including garden sculptures.
Brick, Wood
Utilities Gas:
No
Utilities Hydro:
Yes
Utilities Water:
No
Water Supply Types:
Drilled Well
Sewers:
No
Special Designation:
Unknown
Sewers:
Septic
Air Conditioning:
Wall Unit(s)
Central Vacuum:
No
Seller Property Info Statement:
No
Date Listed:
Jun 01, 2026
Original Price:
Previous Price:
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Virtual Tour

Listed by ROYAL LEPAGE RCR REALTY
Data was last updated June 1, 2026 at 08:15 PM (UTC)
Area Statistics
Listings on market:
194
Avg list price:
$1,499,999
Min list price:
$495,000
Max list price:
$16,800,000
Avg days on market:
38
Min days on market:
1
Max days on market:
634
These statistics are generated based on the current listing's property type and located in Rural Caledon. Average values are derived using median calculations. This data is not produced by the MLS® system.
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.