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Detached for sale at 16927 Winston Churchill Boulevard, Caledon - 5 bedroom, 3 bathroom - Photo 1 of 48
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Detached for sale at 16927 Winston Churchill Boulevard, Caledon - 5 bedroom, 3 bathroom - Photo 7 of 48
Detached for sale at 16927 Winston Churchill Boulevard, Caledon - 5 bedroom, 3 bathroom - Photo 8 of 48
Detached for sale at 16927 Winston Churchill Boulevard, Caledon - 5 bedroom, 3 bathroom - Photo 9 of 48
Detached for sale at 16927 Winston Churchill Boulevard, Caledon - 5 bedroom, 3 bathroom - Photo 10 of 48
Detached for sale at 16927 Winston Churchill Boulevard, Caledon - 5 bedroom, 3 bathroom - Photo 11 of 48
Detached for sale at 16927 Winston Churchill Boulevard, Caledon - 5 bedroom, 3 bathroom - Photo 12 of 48
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Detached for sale at 16927 Winston Churchill Boulevard, Caledon - 5 bedroom, 3 bathroom - Photo 48 of 48
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Active

$4,500,000

16927 Winston Churchill Blvd

Caledon, ON L7K 1H9

16927 Winston Churchill Blvd, CaledonListed at $4,500,000. 5 bedroom, 3 bathroom 2-Storey Detached. MLS® W13224014.

5Beds
3Baths
2500-3000sqft
Detached
2-Storey
25Parking
$4,145.22Taxes/yr · 2026

What's this home worth?

Get a free estimate for 16927 Winston Churchill Blvd

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 TypeDetached
Style2-Storey
CommunityRural Caledon
Approximate Age100+
Rooms11
Kitchens2
Washrooms3
Square Feet2500-3000 sqft
Lot Dimensions1006.41 × 597 ft
Fronting OnEast
Dir/Cross StGrange/Winston Churchill
Garage TypeDetached
Garage Parking Spaces5
DrivePrivate
Parking Drive Spaces20
Total Parking Spaces25
ExteriorBrick, Wood
RoofShingles
FoundationStone
BasementPartially Finished, Partial Basement
Fireplace FeaturesPropane, Wood
Heating TypeForced Air
Heating SourcePropane
A/CWall Unit(s)
WaterDrilled Well
SewersSeptic
PoolInground
Taxes (2026)$4,145.22
HSTIncluded In
Other StructuresWorkshop, Storage, Additional Garage(s), Out Buildings
Listed Date6/1/2026
Days on Market65 days
PossessionTBD

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Listing Courtesy of: ROYAL LEPAGE RCR REALTY

MLS® #W13224014

TRREBMLS®

The listing data is provided under copyright by the Toronto Regional Real Estate Board (TRREB). The listing data is deemed reliable but is not guaranteed accurate by TRREB. 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. Used under license.

© 2026 Toronto Regional Real Estate Board. All rights reserved.

HouseIndex Take: 16927 Winston Churchill Boulevard

This detached (2-Storey) is located in the Rural Caledon neighbourhood of Caledon.

The home offers 5+1 bedrooms, 3 bathrooms.

Features include a partially finished, partial basement basement, 25 parking spaces including a 5-car garage, a fireplace.

Additional details: lot dimensions of 1006.41 × 597 feet.

Listed at $4,500,000 CAD with annual property taxes of $4,145.22 (2026).

About Caledon Real Estate

This Detached is located in the Rural Caledon community in Caledon. Caledon is a vast, scenic municipality in Peel Region spanning the Niagara Escarpment and Oak Ridges Moraine. Bolton is the primary urban centre, while Caledon East and Inglewood offer village living. Popular with buyers seeking acreage, hobby farms, and a rural-meets-suburban lifestyle within commuting distance of Toronto. Detached homes in Caledon are in high demand among families seeking space, privacy, and long-term equity growth.

Niagara Escarpment & Forks of the CreditBolton urban centreHobby farms & rural estate lotsHumber River trails
~60 min commute to downtown TorontoWalkability: Rural — car essential except Bolton core