16927 Winston Churchill Boulevard, Caledon
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. (id:1945)
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Property details for 16927 Winston Churchill Boulevard, Caledon
- Type
- Residential
- Bedrooms
- 5
- Bathrooms
- 3
- Lot Size
- 1006.4 x 597 FT
- Stories
- 2
- Basement
- Partially finished, Partial
- Parking
- Detached Garage, Garage
- Heating
- Forced air, Propane
- Cooling
- Wall unit
- Exterior
- Wood, Brick
- Ownership
- Freehold
- Annual Taxes
- $4,145
Nearby Listings Stat
Estimated price and comparable properties near 16927 Winston Churchill Boulevard
Active Listings
1
Min Price
$4,200,000
Max Price
$4,200,000
Avg Price
$4,200,000
Days on Market
109
days
Sold Listings
0
Min Sold Price
$N/A
Max Sold Price
$N/A
Avg Sold Price
$N/A
Days until Sold
N/A
days
Neighbourhood Census Data
Caledon, Ontario
Population
538
Median Age
49.7
Median Income
$51,584
Dwelling Value
$850,208
Housing Tenure
Owners 91%
Renters 10%
Age Distribution
Dwelling Types
Commute Mode
Education Level
Housing Age
Commute Duration
Avg Household Size: 2.6
Pop. Density: 33.9/km²
Avg Shelter Cost: $1,731/mo
Owners with Mortgage: 45.9%
Owners Spending 30%+: 15.8%
Tenants Spending 30%+: 0%
English only: 87%
English and French: 13%
Neither: 0.9%
Median Household Income: $129,792
Median Employment Income: $49,963
Price History
Listed
June 1, 2026
by ROYAL LEPAGE RCR REALTY
Current Price
$4,200,000
-6.7% from last change
Type
Residential
For Sale
Price Changes
1
| Date | Price | Change |
|---|---|---|
| Current | $4,200,000 | $300,000 (-6.7%) |
| Sep 8, 2026 | $4,500,000 | Listed |
