16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
Rural Caledon, Caledon · Near Grange/Winston Churchill · View map
About this home
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.
The home
- Type
- 2-storey detached home
- Style
- 2-Storey
- Square footage
- 2500-3000 sq ft
- Bedrooms
- 4
- Basement bedrooms
- 1
- Bathrooms
- 3
- Kitchens
- 2
- Rooms
- 11
- Basement
- Partially Finished, Partial Basement
- Lot size
- 1006.4 x 597 ft
- Faces
- East
- Approximate age
- 100+ years
Ownership & fees
- Ownership
- Freehold
- Monthly condo fee
- None
- Exterior
- Brick, Wood
Heating & cooling
- Heating fuel
- Propane
- Heating type
- Forced Air
- Air conditioning
- Wall Unit(s)
- Fireplace
- Yes
Garage & parking
- Garage
- Detached
- Garage spaces
- 5
- Driveway spaces
- 20
- Total parking
- 25
- Parking features
- Private
Taxes & other
- Property taxes
- $4,145/yr
- Tax year
- 2026
- Occupancy
- Owner
- Possession
- TBD
- Cross street
- Grange/Winston Churchill
- Neighbourhood
- Rural Caledon
More
- Price per sq ft
- ~$1,527 (at 2,750 sq ft)
- MLS® number
- W13224014
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The home and its surroundings
- In-Law Capability
- Primary Bedroom - Main Floor
- Guest Accommodations
- Water Treatment
- Generator - Partial
- Lake/Pond
- Wooded/Treed
- Mortgage
- Property tax
- Maintenance fee
Cash needed to close
Estimates only, using Canadian semi-annual compounding, Ontario land transfer tax. Mortgage default insurance is added when you put down less than 20%. Your lender and lawyer will confirm exact numbers.
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
Rural Caledon, Caledon · Near Grange/Winston Churchill
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Listing history for 16927 Winston Churchill Boulevard
See what this home and others at the same address were listed for, what they sold for, and how long it took.
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Frequently asked questions about 16927 Winston Churchill Boulevard
Answers come straight from this home’s MLS® listing.
How much is 16927 Winston Churchill Boulevard listed for, and what would it cost each month?
16927 Winston Churchill Boulevard is listed for $4,200,000. With 20% down ($840,000), the mortgage payment would be roughly $16,942 a month at 4.5% over 30 years. Add property tax and the estimate comes to about $17,287 a month, all in. That figure is an illustration, not a quote.
Is 16927 Winston Churchill Boulevard freehold or a condo, and is there a monthly fee?
16927 Winston Churchill Boulevard is a 2-storey detached home in Rural Caledon, Caledon. Ownership is freehold: you own the home and the lot. There is no monthly condo fee, so the roof, windows, driveway, snow and lawn are yours to look after.
How many bedrooms and bathrooms does 16927 Winston Churchill Boulevard have?
16927 Winston Churchill Boulevard has 4 bedrooms, plus 1 more bedroom in the basement, and 3 bathrooms.
Does 16927 Winston Churchill Boulevard have a garage and parking?
Yes. The listing shows the garage as detached, with room for 5 cars. The driveway adds 20 spaces. In total the listing counts 25 parking spaces.
Does 16927 Winston Churchill Boulevard have a finished basement?
The listing describes the basement as partially finished, partial basement. It counts 1 bedroom on that level. Finished basement space is usually not counted in the square footage shown.
What style of home is 16927 Winston Churchill Boulevard?
16927 Winston Churchill Boulevard is a 2-storey detached home. A 2-storey detached house has its living space on the main floor and the bedrooms upstairs, on its own lot with no shared walls.
Does 16927 Winston Churchill Boulevard have a pool?
Yes. The listing shows inground for the pool. Ask about its age, liner and equipment before you offer, since those are the costly parts to replace.
How big is 16927 Winston Churchill Boulevard, and what is the lot size?
The listing puts the home between 2,500 and 3,000 sq ft. The board reports a range rather than an exact figure, and it usually leaves out the basement. The lot is listed as 1006.4 x 597 ft.
How is 16927 Winston Churchill Boulevard heated and cooled?
Heating is forced air (propane). Cooling is wall unit(s).
What are the property taxes for 16927 Winston Churchill Boulevard?
Property taxes are $4,145 a year (2026), or about $345 a month.
Where is 16927 Winston Churchill Boulevard?
16927 Winston Churchill Boulevard is in the Rural Caledon community of Caledon. The nearest main intersection is Grange/Winston Churchill. The postal code is L7K 1H9.
Is 16927 Winston Churchill Boulevard still for sale?
Yes. It is an active listing (MLS® W13224014). Listings here update from the board through the day and come down once a home sells.
What are similar detached homes near 16927 Winston Churchill Boulevard asking?
Similar detached homes for sale nearby right now include 15668 Shaws Creek Road at $3,200,000 (4 bed), 16735 Shaws Creek Road at $4,699,000 (3+2 bed) and 446 The Grange Side Road at $4,750,000 (3+1 bed). These are asking prices, not sold prices. The Sold history tab shows what homes at this address went for.
What have homes at 16927 Winston Churchill Boulevard sold for?
Recent sales, leases and expired listings for this home and others at the same address are in the Sold history tab, with the price and date of each. It is free for members.
How do I book a showing at 16927 Winston Churchill Boulevard?
Pick a day and time with Book a Tour on this page. Tours are free, with no obligation, in person or by video. You can also call or text 647-931-3923.
Have a different question? Ask about this home and get an answer, usually within the hour.
Similar detached homes nearby
More detached homes for sale near Rural Caledon, picked by style, size and price.
2-storey detached home$3,200,00015668 Shaws Creek Road, Caledon4 bed · 3 bath · Rural CaledonCourtesy of: CHESTNUT PARK REAL ESTATE LIMITEDView home →
2-storey detached home$4,699,00016735 Shaws Creek Road, Caledon3+2 bed · 8 bath · Rural CaledonCourtesy of: RE/MAX REALTY SPECIALISTS INC.View home →
2-storey detached home$4,750,000446 The Grange Side Road, Caledon3+1 bed · 5 bath · Rural CaledonCourtesy of: CHESTNUT PARK REAL ESTATE LIMITEDView home →Courtesy of: ROYAL LEPAGE RCR REALTY
Listing information comes from the Toronto Regional Real Estate Board through PropTx and is deemed reliable but is not guaranteed accurate. It is provided for consumers' personal, non-commercial use. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by The Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA.
*Estimated monthly cost assumes 20% down, a 4.5% rate and a 30-year amortization, plus property tax. For illustration only.