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14294 Winston Churchill Boulevard

Caledon, ON L7C 3E8

Off-Market
4 Beds
3 Baths
3,500 Sq Ft
2 Lot Sq Ft
Single Family Home
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About This Property

In the storybook hamlet of Terra Cotta, Caledon, just steps from the Cataract Trailway and Terra Cotta Conservation Area, this exceptional property offers elegance and a deep connection to nature. Nearly 2.5 acres back onto protected conservation land with no rear neighbours - only forest, fresh air, and birdsong. The lot blends cleared lawn and woodland, with sunny spaces for entertaining and shaded spots for quiet reflection. Your fenced backyard oasis is anchored by a heated saltwater pool with a waterfall, an expansive patio for barbecues and lounging, and the ultimate privacy of your own forest. Inside, vaulted ceilings and large windows flood the main living areas with natural light. The formal dining room sits off the foyer behind French doors, while the grand two-storey living room features a two-way wood-burning fireplace shared with the breakfast room. The chefs kitchen boasts top-of-the-line Miele appliances, including an oversized fridge, built-in oven, sleek cooktop, and flush-mount range hood. A spacious sunken family room off the breakfast and kitchen opens to the backyard. The main floor also offers a laundry room with a walkout and a spa-inspired 3-pc bath with heated floors and a glass shower, perfect after a swim. Upstairs, the open loft hallway provides space for an office, hangout space, or reading nook. Four bedrooms include a sprawling primary suite with his-and-hers walk-in closets. The finished basement offers a huge rec/games room plus a bonus room - ideal as a gym, extra bedroom, or office. An insulated double-car garage with epoxy flooring completes this property. From sunrise coffee on the patio to starlit swims beneath the trees, this Terra Cotta retreat is more than a home - its a lifestyle.

Property Details

StatusOff-Market
Property TypeSingle Family Home
Listing TypeSale
Interior Size3,500 sq ft
Lot Size2 sq ft
Bedrooms4
Bathrooms3
Postal CodeL7C 3E8
Last UpdatedOct 8, 2026 · 2:53 a.m.

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Features & Amenities

  • View
  • Fireplace
  • Air Conditioning
  • Basement

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TRREB MLS® Attribution

MLS® W12591338

Listed by Coldwell Banker Elevate Realty

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.

$2,389,000

last list price — no longer for sale

MLS®W12591338
TypeSingle Family Home
CityCaledon
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Team Filipe · RE/MAX · (647) 210-6070

Listed By

Coldwell Banker Elevate Realty