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14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8

$1,988,000

For SaleDetached · Rural Caledon
4 BD3 BA3500-5000 sqft232.35 x 416.18 ft lot

Price history

Est. monthly payment

$9,250 / mo

20% down · 5.00% · 25 yrs · estimate only

Arranged by The Poised Investor Financial Inc. (FSRA #13759), a related company.

Maintenance fees
N/A
Taxes
$7,275 / year
Listed
Oct 24, 2026
Possession date
N/A
Property type
Detached
Cost per sqft
N/A
Exposure
N/A
Ensuite laundry
N/A
Outdoor space
N/A
Style
2-Storey
Approximate age
31-50
Parking spaces
8
Garage
Attached

About this home

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.

Listed by RE/MAX HALLMARK REALTY LTD.

MLS®: W14114964

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  • Sat, Nov 7, 11:00 a.m. – 1:00 p.m.

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Mortgage calculator

$Loan details
$1,988,000
$100k$5M
20% · $397,600
5%50%
5.00%
0.5%12%
25 years
5 yrs30 yrs
Monthly payment

Principal and interest only, compounded semi-annually. Excludes property tax, insurance, condo fees and mortgage default insurance. An estimate for planning, not an approval or a quoted rate. Mortgage amount $1,590,400, down payment $397,600.

Arranged by The Poised Investor Financial Inc. (FSRA #13759), a related company.

The listing data is provided under copyright by the Toronto Regional Real Estate Board (TRREB). The information provided herein must only be used by consumers that have a bona fide interest in the purchase, sale or lease of real estate and may not be used for any commercial purpose or any other purpose. The data is deemed reliable but is not guaranteed accurate by TRREB. The information provided herein is deemed reliable but is not guaranteed accurate by PROPTX.

Listing data last updated Nov 5, 2026, 10:04 a.m.