$ 1,988,000

14294 Winston Churchill Boulevard, Caledon

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. (id:1945)
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Property details for 14294 Winston Churchill Boulevard, Caledon

Type
Residential
Bedrooms
4
Bathrooms
3
Lot Size
232.4 x 416.2 FT
Stories
2
Basement
Finished, Full
Parking
Attached Garage, Garage
Heating
Forced air, Propane
Cooling
Central air conditioning
Exterior
Stone, Vinyl siding
Ownership
Freehold
Annual Taxes
$7,275

Nearby Listings Stat

Estimated price and comparable properties near 14294 Winston Churchill Boulevard

Active Listings
3
Min Price
$1,799,000
Max Price
$2,174,900
Avg Price
$1,987,300
Days on Market
35
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

Price History

Listed
October 25, 2026
by RE/MAX HALLMARK REALTY LTD.
Current Price
$1,988,000
-16.8% from last change
Type
Residential
For Sale
Price Changes
1
Date Price Change
Current $1,988,000 $401,000 (-16.8%)
Oct 25, 2026 $2,389,000 Listed

Contact Agent Get in touch about 14294 Winston Churchill Boulevard, Caledon

TAMMY SADDLER
TAMMY SADDLER
RE/MAX HALLMARK REALTY LTD.