Aldo Udovicic, BrokerRe/Max Crossroads Realty Inc., Brokerage533 Danforth Rd, Scarborough(416) 438-2536getaldonow@gmail.com
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Listings16927 Winston Churchill Boulevard

16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9

$4,500,000

activeNEW
MLS® #W13224014Single Family Home
5Beds
3Baths
2,500Sq Ft
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9 - Photo 1
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About This Property

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 Type

Single Family Home

Status

Active

MLS® Number

W13224014

Bedrooms

5

Bathrooms

3

Interior Sq Ft

2,500

Listed

June 2, 2026

Features & Amenities

View
Fireplace
Air Conditioning
Basement

Location

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16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9

16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9

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Listing Information

MLS®# W13224014
ROYAL LEPAGE RCR REALTY
Listed June 2, 2026

$4,500,000

Single Family Home · For Sale

5

Beds

3

Baths

2,500

Sq Ft

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Re/Max Crossroads Realty Inc., Brokerage — 533 Danforth Rd, Scarborough ON M1K 1C9