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14294 Winston Churchill Boulevard

Rural Caledon / Caledon, ON L7C 3E8

ActiveFor Sale
4 Beds
3 Baths
3,500 Sq Ft
2 Lot Sq Ft
Single Family Home

About This Property

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.

Property Details

StatusActive
Property TypeSingle Family Home
Listing TypeFor Sale
Interior Size3,500 sq ft
Lot Size2 sq ft
Bedrooms4
Bathrooms3
Taxes (2025)$7,275
Postal CodeL7C 3E8
Last UpdatedOct 29, 2026 · 2:09 a.m.

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Features & Amenities

  • Pool
  • Fireplace
  • Air Conditioning
  • Basement

Buying or selling in Caledon?

Filipe & Isabel Ferreira and the Team Filipe (RE/MAX Ultimate Realty Inc., Brokerage) represent buyers and sellers here. Local guides and live listings below.

Talk to Filipe & Isabel Ferreira →

TRREB MLS® Attribution

MLS® W14114964

Listed by RE/MAX HALLMARK REALTY LTD.

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. The trademarks REALTOR®, REALTORS® and the REALTOR® logo are controlled by CREA and identify real estate professionals who are members of CREA. Listing data provided by the Toronto Regional Real Estate Board (TRREB). The information contained herein is from sources believed to be reliable but is not guaranteed. Information deemed reliable but not guaranteed accurate by TRREB or Team Filipe / RE/MAX.

$1,988,000

asking price

MLS®W14114964
TypeSingle Family Home
CityCaledon
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Team Filipe · RE/MAX · (647) 210-6070

Mortgage Estimate

Est. Monthly Payment

$9,708

/month · $1,590,400 mortgage

Down Payment20% — $397,600
Interest Rate5.5%

Amortization

Total Interest

$1,321,900

Total Cost

$2,912,300

Estimate only. Based on Canadian semi-annual compounding, 25-yr amortization at 5.5%.

Full Mortgage Calculator →

Listed By

RE/MAX HALLMARK REALTY LTD.