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16927 Winston Churchill Boulevard Caledon ON

📍 Caledon, Ontario L7K 1H9

$4,500,000

Active
5BEDS
3BATHS
25PARKING
2KITCHENS
1006.41×597LOT (FT)
100+AGE

📋 Listing Highlights

StatusActive
MLS®W13224014
ListedJun 1, 2026
Days on Market—
Property TypeResidential Freehold
StyleDetached
Cross StreetGrange/Winston Churchill
PossessionTBD
Virtual TourView Tour →

📝 Listing Description

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 Details

Property TypeResidential Freehold
StyleDetached
Bedrooms5
Bathrooms3
Kitchens2
Approx. Age100+

📐 Lot & Land

Lot Width1006.41 ft
Lot Depth597 ft
Cross StreetGrange/Winston Churchill

🔧 Building & Utilities

Heat SourcePropane
HeatingForced Air
CoolingWall Unit(s)
BasementPartially Finished, Partial Basement
GarageDetached
Garage Spaces5
Parking25
ConstructionBoard & Batten , Brick
RoofShingles

💰 Financial

List Price$4,500,000
Annual Taxes$4,145.22 (2026)
PossessionTBD

🧮 Mortgage Calculator

$900,000
Est. Monthly Payment
$22,107/mo
Principal: $3,600,000 · P+I only
Does not include taxes, insurance or CMHC

📍 Location

Listing provided by ROYAL LEPAGE RCR REALTYData via PropTx MLS® / TRREB. Information deemed reliable but not guaranteed.MLS® #W13224014 · Last updated: Jul 14, 2026

Information deemed reliable but not guaranteed. © TRREB / PropTx. MLS® is a trademark of CREA. This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate.