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14294 Winston Churchill Boulevard in Caledon for sale

Asking price
$1,988,000
Estimate (Oct 25)
$1,819,976
MLS #:
W14114964
Type:
Detached, 2-Storey
Approx. SQFT:
3500-5000
Basement:
Finished, Full
4 4
2 232.35 x 416.18 ft lot
PROPERTY HISTORY
SIGN IN REQUIRED
List Date List Price Last Status Sold Date Sold Price Days On Market
0000-00-00 $00000 Exp N/A N/A N/A
0000-00-00 $00000 Ter N/A N/A N/A
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.

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  • Date Listed: Friday, October 23, 2026
  • Listing Brokerage: Re/Max Hallmark Realty Ltd. - Disclaimer: The information contained in this listing has not been verified by Re/Max Hallmark Realty Ltd. and should be verified by the buyer.
  • City: Caledon

    More 4 bedrooms homes for sale in Caledon

  • Neighbourhood: Rural Caledon
  • Major Intersection: Winston Churchill Boulevard / King Street
  • Full Address: 14294 Winston Churchill Boulevard, Caledon, L7C 3E8, Canada, ON, Canada
  • Living Room: hardwood floor, 2 Way Fireplace, Vaulted Ceiling
  • Kitchen: hardwood floor, Quartz Counter, Centre Island
  • Family Room: Broadloom, Sunken Room, W/O To Pool
  • Amenities:
  • Taxes: $7,275.21 (2025)
Foyer19 x 11 ft209 sq ft
Dining13 x 13 ft169 sq ft
Living13 x 16 ft208 sq ft
Kitchen12 x 15 ft180 sq ft
Breakfast13 x 12 ft156 sq ft
Family19 x 19 ft361 sq ft
Laundry8 x 6 ft48 sq ft
Primary21 x 19 ft399 sq ft
Br13 x 12 ft156 sq ft
Br15 x 9 ft135 sq ft
Br16 x 10 ft160 sq ft
Rec31 x 28 ft868 sq ft
Exercise25 x 13 ft325 sq ft

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