14294 Winston Churchill Boulevard
Caledon, ON
- 4 bed
- 3 bath
- approx. 3500-5000 sqft
- Detached
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.
Listing Details
- Taxes (2025)
- $7,275
- Listed
- October 23, 2026
Price History
Listing history
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Property
- Style
- 2-Storey
- Age
- 31-50
- Construction
- Stone, Vinyl Siding
- Roof
- Shingles
- Foundation
- Concrete Block
- Interior
- Auto Garage Door Remote, Central Vacuum, Propane Tank, Storage, Sump Pump, Water Heater Owned, Water Softener, Water Treatment, Bar Fridge
- Lot Size
- 232.35 x 416.18 Feet
Parking
- Garage
- Attached
- Covered Spaces
- 2
- Total Parking
- 8
Utilities
- Sewer
- Septic
- Heat Source
- Propane
Location & Legal
- Cross Street
- Winston Churchill Boulevard / King Street
- Parcel Number
- 142590050
- Possession
- Immediate
- Occupancy
- Owner
Included
- Inclusions
- All Window Coverings and Screens, Including Hardware; Electric Light Fixtures and Ceiling Fans with Remotes; Water Softener; Water Heater; Closet Organizers; All Bathroom Shower Rods and Mirrors; Existing Microwave, Oven, Cooktop, Range Hood, Fridge, Dishwasher; All Garage Door Openers and Remotes; Clothes Washer and Clothes Dryer; Central Vacuum and all Related Equipment; TV Wall Mounts; Pool, Pump and all Related Equipment; Water Collection Barrels; Satellite Dish
- Exclusions
- Ping Pong Table; Outdoor Fireplace, Patio Furniture & Accessories, Hammock and Stand
- Rental Items
- Propane Tank
Community
Postal area L7C
- Population
- 33,846
- Private dwellings
- 9,967
- Median age
- 38
- Average household size
- 3.5
- Median household income
- $134,000
Source: Statistics Canada, 2021 Census of Population, catalogue 98-401-X2021013. Adapted from Statistics Canada. This does not constitute an endorsement by Statistics Canada of this product.
Local market
Residential Freehold in Caledon · last 12 months
- Median sold price
- $1,025,000
- Homes sold
- 769
- Median days on market
- 27
- Sale-to-list price
- 96.3%
Based on 769 recorded sales of residential freehold properties in Caledon over the last 12 months.
Rooms
3-piece on Main, 3-piece on Upper, 2-piece on Lower
Second
- Bedroom15'10" x 9'7"
- Bedroom15'4" x 9'5"
- Bedroom13'1" x 11'11"
- Primary Bedroom21' x 19'2"
Main
- Breakfast12'7" x 12'3"
- Dining Room12'9" x 13'3"
- Family Room19'1" x 19'1"
- Foyer18'7" x 11'2"
- Kitchen12' x 15'1"
- Laundry8'4" x 5'6"
- Living Room12'9" x 15'8"
Basement
- Exercise Room25'4" x 13'5"
- Recreation
Listed by
RE/MAX HALLMARK REALTY LTD.
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Location
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Mortgage Calculator
$397,600
Estimated Monthly Payment
$9,766
Land transfer tax
Ontario land transfer tax only. An estimate — not legal or financial advice. Municipal land transfer tax applies in Toronto and is not included.
Investment Analysis
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Mortgage: $9,766/mo (20% down, 5.5%)
Taxes: $606/mo · Insurance: $497/mo
Estimates only. Consult a financial advisor.
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