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For saleMLS® W14114964

14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8

Rural Caledon · L7C 3E8

$1,988,000

$568 / sq ft

1 weeks on market

Bedrooms
4
Bathrooms
3
Interior
3,500 sf
Parking
8
Lot
232.35 × 416.18 ft
Age
31-50 years

What's special

  • Attached garage
  • Pool
  • Central air
  • Finished basement
  • 2 fireplaces
  • Auto garage door remote
  • Central vacuum
  • Propane tank

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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.

Rooms

13 rooms. Dimensions as published by the listing brokerage.

Room dimensions and features
RoomLevelDimensionsFeatures
FoyerMain5.67 × 3.41 m18.6 × 11.2 ftHardwood Floor · Double Closet · Vaulted Ceiling(s)
Dining RoomMain3.89 × 4.04 m12.8 × 13.3 ftHardwood Floor · French Doors · Crown Moulding
Living RoomMain3.89 × 4.78 m12.8 × 15.7 ftHardwood Floor · 2 Way Fireplace · Vaulted Ceiling(s)
KitchenMain3.67 × 4.60 m12.0 × 15.1 ftHardwood Floor · Quartz Counter · Centre Island
BreakfastMain3.84 × 3.73 m12.6 × 12.2 ftHardwood Floor · 2 Way Fireplace · Large Window
Family RoomMain5.82 × 5.82 m19.1 × 19.1 ftBroadloom · Sunken Room · W/O To Pool
LaundryMain2.53 × 1.68 m8.3 × 5.5 ftTile Floor · W/O To Yard · Laundry Sink
Primary BedroomSecond6.41 × 5.83 m21.0 × 19.1 ftBroadloom · Sunken Room · His and Hers Closets
BedroomSecond3.99 × 3.63 m13.1 × 11.9 ftBroadloom · Closet · Window
BedroomSecond4.67 × 2.87 m15.3 × 9.4 ftBroadloom · Closet · Window
BedroomSecond4.83 × 2.93 m15.8 × 9.6 ftBroadloom · Closet · Window
RecreationBasement9.46 × 8.49 m31.0 × 27.9 ftBroadloom · Fireplace · Above Grade Window
Exercise RoomBasement7.71 × 4.09 m25.3 × 13.4 ftBroadloom · Above Grade Window · Recessed Lighting

Features

  • Auto Garage Door Remote
  • Central Vacuum
  • Propane Tank
  • Storage
  • Sump Pump
  • Water Heater Owned
  • Water Softener
  • Water Treatment
  • Bar Fridge

Property details

Property

Property type
detached
Bedrooms
4
Bathrooms
3
Interior size
3,500 sq ft
Year built
31-50
Lot size
232.35 × 416.18 ft
Possession
Immedaite

Interior

Basement
Finished, Full
Heating
Forced Air · Propane
Cooling
Central Air
Fireplaces
2
Exposure
West

Exterior & services

Construction
Stone, Vinyl Siding
Garage
Attached
Parking spaces
8
Pool
Inground,Salt
Sewer
Septic

Costs

List price
$1,988,000
Property taxes
$7,275 / year (2025)
Price per sq ft
$568
Rental items
Propane Tank

Listing

MLS® number
W14114964
Status
For sale
Listed
October 25, 2026
Days on market
11
Last updated
November 3, 2026
Listing brokerage
RE/MAX HALLMARK REALTY LTD.

Price & sale history

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Before you make an offer

What this home costs beyond the asking price, and how that price compares to what else is on the market.

How this price compares

This home is priced in line with comparable listings — about 71% of comparable detached listings in Rural Caledon are asking less.

$1.03MMedian $1.50M$3.47M
This home
$568 / sq ft
Comparable median
$750 / sq ft

Based on 95 comparable active detached listings in Rural Caledon. These are asking prices, not sale prices.

Mortgage estimate

Down payment20.0% · minimum $397,600
$397,600
Interest rate5-year fixed, illustrative only
4.49%
Amortization
Principal & interest
$8,793.59
Property tax (est.)
$606.27
Estimated monthly
$9,400

Estimate only. Excludes CMHC insurance premiums, which apply below 20% down, and does not constitute a mortgage approval or an offer of credit.

Land transfer tax

Payable on closing, on top of the purchase price.

Ontario
$36,235
Total due on closing
$36,235

An estimate on the asking price of $1,988,000. Rates current as of September 2026; confirm the final figure with your real estate lawyer.

Listing courtesy of RE/MAX HALLMARK REALTY LTD.. Listing data is provided in part by the Toronto Regional Real Estate Board (TRREB) and is deemed reliable but is not guaranteed accurate. Information is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties. Data is updated every 15 minutes.

$1,988,000

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