$1,988,000
14294 Winston Churchill Blvd
Caledon, ON L7C 3E8
14294 Winston Churchill Blvd, Caledon — Listed at $1,988,000. 4 bedroom, 3 bathroom 2-Storey Detached. MLS® W14114964.
Possession · seller's timeline
Immediate (Immedaite)
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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.
Property Details
Property Insights
Listing Courtesy of: RE/MAX HALLMARK REALTY LTD.
MLS® #W14114964


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HouseIndex Take: 14294 Winston Churchill Boulevard
This detached (2-Storey) is located in the Rural Caledon neighbourhood of Caledon.
The home offers 4 bedrooms, 3 bathrooms.
Features include a finished, full basement, 8 parking spaces including a 2-car garage, a fireplace.
Additional details: lot dimensions of 232.35 × 416.18 feet.
Listed at $1,988,000 CAD with annual property taxes of $2,025 (2025).
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About Caledon Real Estate
This Detached is located in the Rural Caledon community in Caledon. Caledon is a vast, scenic municipality in Peel Region spanning the Niagara Escarpment and Oak Ridges Moraine. Bolton is the primary urban centre, while Caledon East and Inglewood offer village living. Popular with buyers seeking acreage, hobby farms, and a rural-meets-suburban lifestyle within commuting distance of Toronto. Detached homes in Caledon are in high demand among families seeking space, privacy, and long-term equity growth.

















































