Advantage Group Real Estate
14294 Winston Churchill Boulevard • Caledon, ON photo 1
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New1 / 50
$1,988,000
14294 Winston Churchill Boulevard • Caledon, ONNew
Courtesy of RE/MAX HALLMARK REALTY LTD.
4
Bedrooms
3
Bathrooms
3500-5000
Square feet
8
Parking

About this home

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 type
Detached
Style
2-Storey
Approx. age (yrs)
31-50
Total rooms
10
Lot size
232.35 × 416.18 ft
Property taxes
$2,025 (2025)
Occupancy
Immedaite
Days on market
1
Status
Active
MLS®

Property history

Recently sold nearby

Listing data last updated: Oct 25, 2026, 7:31 a.m. EDT via TRREB IDX.

First listed: Oct 25, 2026, 7:31 a.m. EDT.