14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
Rural Caledon, Caledon · Near Winston Churchill Boulevard / King Street · View map
About this home
Backing onto protected conservation land with no rear neighbours, this 2.43-acre Terra Cotta estate sits steps from the Caledon Trailway and Terra Cotta Conservation Area. Mature forest frames the property, while open lawn and established perennial beds create spaces to play, entertain and unwind. Garden paths wind past the perennials and beneath a charming arbour to quiet seating areas, with fresh blooms from spring through fall and blazing autumn colour in the forest beyond. The fully fenced pool and patio area make your backyard a private resort. The heated saltwater pool is soft and gentle on skin and eyes, with no harsh chlorine smell, and the waterfall adds a soothing soundtrack to long summer afternoons. Heating extends the swim season from late spring into fall. The large patio offers room for dining, lounging and barbecues, all with the forest as your backdrop. Inside are 3,716 sq ft above grade plus a finished lower level, over 4,700 sq ft in all. The two-storey living room has a vaulted ceiling and a two-way wood-burning fireplace shared with the breakfast room. The kitchen features Miele appliances, including an oversized fridge, built-in oven, cooktop and flush-mount hood, and opens to a sunken family room that walks out to the yard. The main floor also has a formal dining room behind French doors, laundry with a walkout, and a 3-pc bath with heated floor and glass shower, steps from the pool. Upstairs, an open loft works as an office or reading nook, and four bedrooms include a primary suite with his-and-hers walk-in closets. The finished basement adds a large rec room plus a bonus room for a gym, guest room or office. Insulated double garage with epoxy floor. Morning coffee under the arbour, an evening swim beneath the trees: this is country living, minutes from town. Offers welcome Sunday, November 8 at 6 PM. Ontario's Conservation Land Tax incentive program reduces taxable property amount by 1.39 acres from the total area of 2.42 acres.
The home
- Type
- 2-storey detached home
- Style
- 2-Storey
- Square footage
- 3500-5000 sq ft
- Bedrooms
- 4
- Bathrooms
- 3
- Kitchens
- 1
- Rooms
- 10
- Basement
- Finished, Full
- Lot size
- 232.4 x 416.2 ft
- Faces
- West
- Approximate age
- 31-50 years
Ownership & fees
- Ownership
- Freehold
- Monthly condo fee
- None
- Security
- Security System, Monitored
- Exterior
- Stone, Vinyl Siding
Heating & cooling
- Heating fuel
- Propane
- Heating type
- Forced Air
- Air conditioning
- Central Air
- Fireplace
- Yes
- Central vacuum
- Yes
Garage & parking
- Garage
- Attached
- Garage spaces
- 2
- Driveway spaces
- 6
- Total parking
- 8
- Parking features
- Private Double
Taxes & other
- Property taxes
- $7,275/yr
- Tax year
- 2025
- Occupancy
- Owner
- Possession
- Immedaite
- Cross street
- Winston Churchill Boulevard / King Street
- Neighbourhood
- Rural Caledon
More
- Price per sq ft
- ~$468 (at 4,250 sq ft)
- MLS® number
- W14114964
No matching details. Ask Will instead
The home and its surroundings
- Auto Garage Door Remote
- Central Vacuum
- Propane Tank
- Storage
- Sump Pump
- Water Heater Owned
- Water Softener
- Water Treatment
- Bar Fridge
- Fenced Yard
- Greenbelt/Conservation
- Lake/Pond
- Wooded/Treed
- Backs On Green Belt
- Landscaped
- Patio
- Privacy
- 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.
14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
Rural Caledon, Caledon · Near Winston Churchill Boulevard / King Street
Get directionsWhat’s nearbySchools nearby
Open this tab to load nearby schools.
Your commute
Enter where you go every day to see real drive times:
Listing history for 14294 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.
Sold prices are for members. It’s free, takes a few seconds, and unlocks the sale history on every listing.
Frequently asked questions about 14294 Winston Churchill Boulevard
Answers come straight from this home’s MLS® listing.
How much is 14294 Winston Churchill Boulevard listed for, and what would it cost each month?
14294 Winston Churchill Boulevard is listed for $1,988,000. With 20% down ($397,600), the mortgage payment would be roughly $8,019 a month at 4.5% over 30 years. Add property tax and the estimate comes to about $8,625 a month, all in. That figure is an illustration, not a quote.
Is 14294 Winston Churchill Boulevard freehold or a condo, and is there a monthly fee?
14294 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 14294 Winston Churchill Boulevard have?
14294 Winston Churchill Boulevard has 4 bedrooms and 3 bathrooms.
Does 14294 Winston Churchill Boulevard have a garage and parking?
Yes. The listing shows the garage as attached, with room for 2 cars. The driveway adds 6 spaces. In total the listing counts 8 parking spaces.
Does 14294 Winston Churchill Boulevard have a finished basement?
The listing describes the basement as finished, full. Finished basement space is usually not counted in the square footage shown.
What style of home is 14294 Winston Churchill Boulevard?
14294 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 14294 Winston Churchill Boulevard have a pool?
Yes. The listing shows inground, salt for the pool. Ask about its age, liner and equipment before you offer, since those are the costly parts to replace.
How big is 14294 Winston Churchill Boulevard, and what is the lot size?
The listing puts the home between 3,500 and 5,000 sq ft. The board reports a range rather than an exact figure, and it usually leaves out the basement. The lot is listed as 232.4 x 416.2 ft.
How is 14294 Winston Churchill Boulevard heated and cooled?
Heating is forced air (propane). Cooling is central air.
What are the property taxes for 14294 Winston Churchill Boulevard?
Property taxes are $7,275 a year (2025), or about $606 a month.
Where is 14294 Winston Churchill Boulevard?
14294 Winston Churchill Boulevard is in the Rural Caledon community of Caledon. The nearest main intersection is Winston Churchill Boulevard / King Street. The postal code is L7C 3E8.
Is 14294 Winston Churchill Boulevard still for sale?
Yes. It is an active listing (MLS® W14114964). Listings here update from the board through the day and come down once a home sells.
What are similar detached homes near 14294 Winston Churchill Boulevard asking?
Similar detached homes for sale nearby right now include 1 Cedar Drive at $1,849,999 (4 bed), 70 Stratford Drive at $1,644,161 (4 bed) and 30 Brookwater Crescent at $1,549,990 (4+3 bed). These are asking prices, not sold prices. The Sold history tab shows what homes at this address went for.
What have homes at 14294 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 14294 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$1,849,9991 Cedar Drive, Caledon4 bed · 4 bath · Rural CaledonCourtesy of: RE/MAX REAL ESTATE CENTRE INC.View home →
2-storey detached home$1,644,16170 Stratford Drive, Caledon4 bed · 4 bath · Rural CaledonCourtesy of: THE CANADIAN HOME REALTY INC.View home →
2-storey detached home$1,549,99030 Brookwater Crescent, Caledon4+3 bed · 7 bath · Rural CaledonCourtesy of: HOMELIFE/MIRACLE REALTY LTDView home →Courtesy of: RE/MAX HALLMARK REALTY LTD.
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.