14409 Winston Churchill Boulevard

Caledon, Ontario L7C 1S6

Overview

At a glance

Days on market109 days
ListedJul 9, 2026
UpdatedOct 15, 2026
Size1500-2000 sq ft
Lot155.98 x 290.2 Feet
Property taxes$4,753 (2026)
Parking12 spaces
BasementNone
MLS® numberW13544076
Data sourcePropTx MLS® System
Listing brokerageiCloud Realty Ltd.

About this home

A rare offering in Terra Cotta! Nestled among mature trees on a picturesque and private lot, this charming 4-bedroom home is located in one of Peel's most coveted rural communities. Combining the tranquility of country living with the convenience of nearby amenities, this is a property with remarkable long-term appeal and value. The home features a spacious kitchen, an updated washroom, renovated flooring, and fresh paint throughout, providing a comfortable space to enjoy from day one while offering the flexibility to personalize over time. Whether your plans include tasteful enhancements, a future addition, or the design and construction of a custom estate home, the possibilities are endless. Premium treed properties in this highly desirable location seldom become available. Surrounded by natural beauty and offering outstanding privacy, this is your chance to create a truly special country retreat tailored to your vision and lifestyle.

Details

Property

Style
Bungalow
Fronting on
East
Cross street
Winston Churchill Blvd & WellingtonRd 42
Community
Rural Caledon
Municipality
Caledon

Inside

Bedrooms above grade
4
Bathrooms
1
Kitchens
1
Basement
None
Family room
No
Fireplace
Propane
Interior features
Auto Garage Door Remote, Carpet Free, Primary Bedroom - Main Floor, Propane Tank, Water Heater Owned, Water Softener, Water Purifier, Water Treatment

Utilities

Heating
Baseboard
Heating fuel
Electric
Cooling
Window Unit(s)
Sewer
Septic

Building

Construction
Brick
Foundation
Slab
Roof
Asphalt Shingle
Pool
None

Parking

Garage
Detached
Parking spaces
10
Total parking
12
Driveway
Private, Private Double, Front Yard Parking

Land

Frontage
155.98
Depth
290.2
Lot size units
Feet
Waterfront
No
Property features
Greenbelt/Conservation, Park, Wooded/Treed, School Bus Route
Rooms (10)
RoomLevelSizeFeatures
KitchenMain5.61 x 5.07B/I Dishwasher, Vinyl Floor, Breakfast Area
Living RoomMain3.7 x 6.67Vinyl Floor, Gas Fireplace, Large Window
Primary BedroomMain3.96 x 3.94Vinyl Floor, Window
Bedroom 2Main4.01 x 2.76Vinyl Floor, Window
Bedroom 3Main3.24 x 4.08Vinyl Floor, Window
Bedroom 4Main2.88 x 3.98Vinyl Floor, Window
BathroomMain3.46 x 2.67Vinyl Floor, 3 Pc Bath
LaundryMain3.85 x 2.42Vinyl Floor, Laundry Sink
Utility RoomMain2.29 x 2.5
OtherMain2.54 x 2.31
Value

What it’s worth

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Market read

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History

Listing history

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Compare

How it compares

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Neighbourhood

Around Caledon

What’s nearby

Backs onto woodsOn a busier streetBackyard faces east

  • ParkTerra Cotta Conservation Areaabout 8 min walk
  • Playground about 2.5 km
  • TrailBruce Trailabout 2 min walk
  • River or lake about 11 min walk
  • DowntownBallinafadabout 5.5 km
  • Golf courseCaledon Golf and Country Clubabout 6.5 km
  • HospitalGeorgetown Hospitalabout 9.7 km
  • Highway on-ramp about 8.2 km
  • GO or train stationGeorgetownabout 8.9 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.

On the map

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Homes within 3 km that sold in the last year, what they sold for and how fast.

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Community

The Caledon market

Caledon sale prices

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Costs

What it would cost

%
%
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 iCloud 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 10:38 p.m.

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