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For Sale
$4,500,000
Estimated monthly cost
$21,283/mo
20% down • 5.00% rate • 25 yr • incl. tax

16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9

Rural Caledon
5
Beds
3
Baths
25
Parking
2,500–3,000 ft²
Size
Property type
Detached
Listed
20 Days
Annual taxes
$4,145 /yr (2026)
MLS® number
W13224014
Listing brokerage
ROYAL LEPAGE RCR REALTY

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
Style
2-Storey
Basement
Finished Basement
Exterior Finish
Brick, Wood
Heating
Forced Air · Propane
Cooling
Wall Unit(s)
Pool
Inground
Building Age
100+
Parking
Garage Type
Detached
Total Parking
25
Land
Lot Size
1006.41 × 597 ft
Lot Features
Lake/Pond, Wooded/Treed
Sewer
Septic
Listing
MLS® Number
W13224014
Listed Date
Jun 1, 2026
Last Updated
Jun 2, 2026

About Rural Caledon

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Location

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$4,500,000
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9

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Listing data is provided by the Toronto Regional Real Estate Board (TRREB) and PropTx under the Internet Data Exchange (IDX) program. The information is deemed reliable but is not guaranteed accurate by TRREB, PropTx, CREA or DistrictIQ Inc., Brokerage, may not reflect the most current status, and is subject to errors, omissions, prior sale, change, or withdrawal without notice. Listings should be independently verified.

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