14294 Winston Churchill Boulevard

Caledon, Ontario L7C 3E8

Overview

At a glance

Days on market1 day
ListedOct 25, 2026
UpdatedOct 26, 2026
Building age31-50 years
Size3500-5000 sq ft
Lot232.35 x 416.18 Feet
Property taxes$7,275 (2025)
Parking8 spaces
BasementFinished, Full
MLS® numberW14114964
Data sourcePropTx MLS® System
Listing brokerageRE/MAX HALLMARK REALTY LTD.

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.

Details

Property

Style
2-Storey
Building age
31-50
Fronting on
West
Cross street
Winston Churchill Boulevard / King Street
Community
Rural Caledon
Municipality
Caledon

Inside

Bedrooms above grade
4
Bathrooms
3
Kitchens
1
Basement
Finished, Full
Family room
Yes
Fireplace
Propane, Wood
Interior features
Auto Garage Door Remote, Central Vacuum, Propane Tank, Storage, Sump Pump, Water Heater Owned, Water Softener, Water Treatment, Bar Fridge

Utilities

Heating
Forced Air
Heating fuel
Propane
Cooling
Central Air
Sewer
Septic

Building

Construction
Stone, Vinyl Siding
Foundation
Concrete Block
Roof
Shingles
Exterior features
Backs On Green Belt, Landscaped, Patio, Privacy
Pool
Inground, Salt

Parking

Garage
Attached
Parking spaces
6
Total parking
8
Driveway
Private Double

Land

Frontage
232.35
Depth
416.18
Lot size units
Feet
Lot size (acres)
2-4.99
Waterfront
No
Property features
Fenced Yard, Greenbelt/Conservation, Lake/Pond, Wooded/Treed
Rooms (13)
RoomLevelSizeFeatures
FoyerMain5.67 x 3.41Hardwood Floor, Double Closet, Vaulted Ceiling(s)
Dining RoomMain3.89 x 4.04Hardwood Floor, French Doors, Crown Moulding
Living RoomMain3.89 x 4.78Hardwood Floor, 2 Way Fireplace, Vaulted Ceiling(s)
KitchenMain3.67 x 4.6Hardwood Floor, Quartz Counter, Centre Island
BreakfastMain3.84 x 3.73Hardwood Floor, 2 Way Fireplace, Large Window
Family RoomMain5.82 x 5.82Broadloom, Sunken Room, W/O To Pool
LaundryMain2.53 x 1.68Tile Floor, W/O To Yard, Laundry Sink
Primary BedroomSecond6.41 x 5.83Broadloom, Sunken Room, His and Hers Closets
BedroomSecond3.99 x 3.63Broadloom, Closet, Window
BedroomSecond4.67 x 2.87Broadloom, Closet, Window
BedroomSecond4.83 x 2.93Broadloom, Closet, Window
RecreationBasement9.46 x 8.49Broadloom, Fireplace, Above Grade Window
Exercise RoomBasement7.71 x 4.09Broadloom, Above Grade Window, Recessed Lighting
Value

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History

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Neighbourhood

Around Caledon

What’s nearby

On a busier streetBackyard faces south

  • ParkTerra Cotta Conservation Areaabout 2 min walk
  • Playground about 19 min walk
  • TrailA.F. Coventry Trailabout 4 min walk
  • River or lake about 8 min walk
  • DowntownBallinafadabout 5.8 km
  • Golf courseCaledon Golf and Country Clubabout 7 km
  • HospitalGeorgetown Hospitalabout 8.7 km
  • Highway on-ramp about 6.9 km
  • GO or train stationGeorgetownabout 7.9 km

Approximate: straight-line distances, and the backyard and street worked out from the map pin and map data © OpenStreetMap contributors. Check school boundaries with the school board.

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Community

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Costs

What it would cost

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%
An example rate. Use the one your lender quotes.
Every monthEstimate
Mortgage payment$0
Property tax$0
Monthly total$0
At closing
Ontario land transfer tax$0

Estimates only, not financial advice. Uses Canadian semi-annual compounding, the minimum down payment and mortgage insurance rules, and Ontario’s land transfer tax brackets. Your lender and lawyer confirm the real numbers. Legal fees, title insurance and moving costs aren’t included.

Listing courtesy of RE/MAX HALLMARK REALTY LTD.. Listing information from the PropTx MLS® System. Each listing shows the brokerage that represents it. 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. Information is deemed reliable but is not guaranteed accurate by PropTx. Last updated October 26, 2026 at 4:41 p.m.

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