14294 Winston Churchill Boulevard, Caledon

14294 Winston Churchill Boulevard
14294 Winston Churchill Boulevard
14294 Winston Churchill Boulevard
+47
4
 bed
3
 bath
8
 parking
3500 - 5000
 sqft
Detached
$1,988,000
For Sale
3 hours
 on site
$1,988,000
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Size
-
Lot size
2 sqft
Street frontage
-
Possession
2026-11-15
Price per sqft
$398 - $568
Taxes
$2,025 (2025)
Parking Type
-
Style
2-Storey
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Description
Backing onto protected conservation land with no rear neighbours, this 2.43-acre Terra Cotta estate sits steps from the Cataract 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 backyard is 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.
Broker: RE/MAX HALLMARK REALTY LTD.
MLS®#: W14114964
Property details
Parking:
8
Parking type:
-
Property type:
Detached
Heating type:
Forced Air
Style:
2-Storey
MLS Size:
3500-5000 sqft
Lot front:
232 Ft
Lot depth:
416 Ft
Listed on:
Oct 25, 2026
Show all details
Rooms
LevelNameSizeFeatures
Main
Family Room
19.1 x 19.1 ft
Main
Foyer
18.6 x 11.2 ft
Second
Bedroom
15.8 x 9.6 ft
Show all
Instant estimate:
orto view instant estimate
$155,879
lower than listed price
i
High
$1,897,705
Mid
$1,832,121
Low
$1,736,016
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About 14294 Winston Churchill Boulevard

Located at 14294 Winston Churchill Boulevard, this Caledon detached house is available for sale. It has been listed at $1988000 since October 2026. This detached house has 4 beds, 3 bathrooms and is 3500-5000 sqft. Situated in Caledon's Rural Halton Hills neighbourhood, Glen Williams, Limehouse, Georgetown and Northwest Brampton are nearby neighbourhoods.

For grabbing your groceries, Glen Oven Cafe is a 7-minute drive.

Getting around the area will require a vehicle, as the nearest transit stop is a Bus Stop (N Veterans Dr / Mayfield Rd) and is a 9-minute drive