Haider BokhariAI real estate platform · RE/MAX Real Estate Centre Inc.
For Sale

16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9

Rural Caledon · Caledon · ON · L7K 1H9

$4,500,000
$1,800/sqft
5 beds3 baths2,500–3,000 sqft25 parkingDetachedPartially Finished, Partial Basement basement
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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
Detached
Style
2-Storey
Bedrooms
5
Bathrooms
3
Square Feet
2,500–3,000
Year Built
Parking
25
Basement
Partially Finished, Partial Basement
Taxes
$4,145/yr
Market insight: Homes in Rural Caledon have stayed in demand, with well-priced properties moving quickly. Ask about recent comparable sales before you make an offer.

MLS® · REALTOR®

Listing courtesy of ROYAL LEPAGE RCR REALTY, Brokerage.

The trademarks MLS®, Multiple Listing Service® and the associated logos identify professional services rendered by REALTOR® members of CREA to effect the purchase, sale and lease of real estate as part of a cooperative selling system. The trademarks REALTOR®, REALTORS® and the REALTOR® logo identify real estate professionals who are members of CREA. Information is deemed reliable but is not guaranteed accurate by TRREB or CREA. Listing data is provided for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data last updated Jul 22, 2026, 12:53 p.m..

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