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Caledon, King, Toronto, New Tecumseth & Orangeville(437) 228-3434
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MLS® W13544076For SaleDetached

14409 Winston Churchill Blvd

Rural Caledon, Caledon, Ontario L7C 1S6

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14409 Winston Churchill Blvd, Caledon, photo 1
Asking$1,170,000
Bedrooms
4
Bathrooms
1
Size
1,500–2,000sq ft
Per sq ft
$669at the range’s middle
Lot
155.98 x 290.2 ft
Tax a year
$4,7532026 tax year
Parking
122 detached
Days on market
Members

The brief

About 14409 Winston Churchill Blvd

14409 Winston Churchill Blvd is a 4-bedroom, 1-bathroom detached house in Rural Caledon, Caledon, listed for sale at an asking price of $1,170,000 (MLS® W13544076).

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.

Insights

  • Condition Score

    Good

    2 documented update signals

    Source: Listing age, structured features and disclosed update language; not an inspection.

  • Cashflow Quality

    Shortfall

    −$2,384/mo against the cost of owning (20% down, 4.8%, 25 yrs)

    Source: Median of 8 homes with 4 bedrooms for lease in Rural Caledon right now. Cost of owning counts the mortgage and property tax.

Condition uses listing-record signals, not an inspection.

The home

Key facts

Tax
$4,753 / 2026
MLS® number
W13544076
Board
TRREB MLS®
Property Type
Detached
Days on market
Size
1500-2000 sqft
Lot Size
155.98 x 290.2 ft
Listed on
Parking
2 Detached, 12 Parking
Listing brokerage: iCloud Realty Ltd.Data source: TRREB MLS®Information deemed reliable but not guaranteed. Contained information is subject to errors, omissions, and changes without notice. Information should be independently verified.

Property details

Property

Property Type
Detached
Style
Bungalow
Community
Rural Caledon
Municipality
Caledon

Building

Size
1500-2000 sqft
Construction
Brick

Inside

Bedrooms
4
Bathrooms
1
Bathroom Details
1 × 3pc Main
Basement Type
None
Kitchens
1

Parking

Driveway
Private, Pvt Double, Front Yard
Garage Type
Detached
Garage
2
Additional Parking
10
Total Parking
12

Utilities

Water
Well
Cooling
Window Unit
Heating Type
Baseboard

Land

Sewer
Septic
Frontage
155.98 ft
Depth
290.2 ft
Lot Size
155.98 x 290.2 ft

Additional

Foundation
Slab
Roof
Asphalt Shingle
Fireplace
Yes
Pool
None
Den
No
Family room
No
Extras
All electric light fixtures, existing appliances (B/I dishwasher, stove, fridge, clothes washing machine and dryer), window coverings, A/C window units, portable generator, garage remote. All chattels and fixture are "as in" and in "as is" condition.

Rooms

RoomSizeFeaturesLevel
Kitchen5.07 × 5.61 mB/I Dishwasher, Vinyl Floor, Breakfast AreaMain
Living6.67 × 3.7 mVinyl Floor, Gas Fireplace, Large WindowMain
Primary3.94 × 3.96 mVinyl Floor, WindowMain
2nd Br2.76 × 4.01 mVinyl Floor, WindowMain
3rd Br4.08 × 3.24 mVinyl Floor, WindowMain
4th Br3.98 × 2.88 mVinyl Floor, WindowMain
Bathroom2.67 × 3.46 mVinyl Floor, 3 Pc BathMain
Laundry2.42 × 3.85 mVinyl Floor, Laundry SinkMain
Utility2.5 × 2.29 m—Main
Other2.31 × 2.54 m—Main

Listing history

Buy/sell history for 14409 Winston Churchill Blvd, Caledon, Ontario

Sale history on this site covers the last 2 years, the window permitted under the TRREB MLS® VOW agreement.

Date StartDate EndList PricePriceEventListing ID
Date StartN/AN/A$1,170,000N/APcW13544076

Members see the full history. Prices are hidden from signed-out visitors.

The numbers

Mortgage Calculator

Plan with the current asking price

20% · $234,000

CMHC insurance: not required at 20% down. Payments use Canadian semi-annual compounding.

Mortgage Details

4.8% · 5-year term · 25-year amortization · 20% down

Total down payment
$234,000
Total mortgage amount
$936,000
Total interest payment
$665,400
Total purchase cost
$1,835,400
Mortgage payment
$5,338/mo

Cash Flow Analysis

If you rented this home out at 20% down

Break-even down payment

56%

Monthly carrying cost

$5,734
−$2,384per month
  • Rent $3,350
  • Shortfall $2,384

Rental income opens at $3,350, the median asking rent of 8 comparable homes for lease in Rural Caledon. Type over it with the rent you expect. This is a planning tool, not advice.

Land transfer tax on this home

Ontario land transfer tax
$19,875
Total land transfer tax
$19,875
First-time buyer rebates (Ontario up to $4,000)
−$4,000
Total for first-time buyers
$15,875
See how this is worked out
0.5% on the first $55,000
$275
1.0% from $55,000 to $250,000
$1,950
1.5% from $250,000 to $400,000
$2,250
2.0% from $400,000 to $1,170,000
$15,400
Ontario total
$19,875

An estimate at the asking price, for a home with one or two single-family residences. Your lawyer confirms the exact amount.

Estimate

Estimated value requires sign in

Market estimates use sold comparables and are available after you sign in and accept MLS® VOW terms.

The estimate is an automated value built from public and MLS® data. It is not an appraisal; ask Kassaundra Dobson, Broker of Record for a full comparative market analysis.

Comparable sales

Comparable sales require sign in

Closing prices and sold comps are available to registered visitors who accept MLS® VOW terms on this site.

The land

Lot

Lot area
45,265 sq ft4,205 m²
Street frontage
155.98 ft47.5 m
Depth
290.2 ft88.5 m
155.98 × 290.2 ftWINSTON CHURCHILL BLVD

The area is the frontage multiplied by the depth, so boundaries are approximate. Confirm with a survey before you buy.

Source: the MLS® listing record, measured by GeoWarehouse.

Land and environment

Public records about this location. Not part of the MLS® listing and not provided by the listing brokerage.

14 records · 10 on fileRead 2026-10-28
250 m500 m1 km2 kmBeyond · area-wideNot in Credit Valley Conservation’s mapped regulated areaA mapped wetland is within 120 m5 water-supply wells recorded within 250 mGroundwater recorded about 5.5 m below ground nearbyBedrock about 4.6 m down nearbyInside the Greenbelt (Niagara Escarpment Plan) and the Niagara Escarpment plan area (Escarpment Protection Area)Nearest airport: 7.0 kmA trail on the Ontario trail network within 1 km3 licensed pits or quarries within 2 kmNo recorded oil, gas or salt well within 250 mNo facility within 1 km reports pollutant releases to Environment CanadaNo federal contaminated site within 1 kmElectricity is distributed here by Hydro One Networks Inc.Fibre to the home, Cable, DSL internet listed for this area
On record Checked, none on record

Water and conservation5

  • Not in Credit Valley Conservation’s mapped regulated areaAt the address
  • A mapped wetland is within 120 mDevelopment close to a wetland can need extra review.120 m
  • 5 water-supply wells recorded within 250 mAll were drilled for domestic use. From Ontario’s well records; locations can be approximate. The records do not show how this home gets its water. Wells nearby typically go down about 22.9 m.250 m
  • Groundwater recorded about 5.5 m below ground nearbyThe middle water level in the well records within 500 m (16 records). It changes with the season and from spot to spot.500 m
  • Bedrock about 4.6 m down nearbyThe middle depth to bedrock in the well records within 500 m.500 m

Credit Valley Conservation · Province of Ontario open data

Planning and building activity2

  • Inside the Greenbelt (Niagara Escarpment Plan) and the Niagara Escarpment plan area (Escarpment Protection Area)These provincial plans set policies on new buildings, new lots and some changes to the land; the municipality can say which apply to this property.At the address
  • Nearest airport: 7.0 km7 km

Province of Ontario open data

Around the home1

  • A trail on the Ontario trail network within 1 km1 km

Province of Ontario open data

Environmental records4

  • 3 licensed pits or quarries within 2 kmThe nearest is 690 m away, as mapped.2 km
  • No recorded oil, gas or salt well within 250 m250 m
  • No facility within 1 km reports pollutant releases to Environment CanadaOnly facilities above the inventory’s reporting thresholds are listed.1 km
  • No federal contaminated site within 1 kmThe federal inventory covers federal land only; it says nothing about provincial or private sites.1 km

Province of Ontario open data · Government of Canada open data

Power and internet2

  • Electricity is distributed here by Hydro One Networks Inc.At the address
  • Fibre to the home, Cable, DSL internet listed for this areaFibre to the home: Standard Broadband. Cable: Rogers. DSL: Bell. Fixed wireless: Bell, QuaenetFi, Rogers, Routcom, SkyChoice Communications, Standard Broadband, Vianet. Mobile: Bell, Freedom Mobile, Rogers, Telus. Satellite: Xplore. ISED’s list for the surrounding ~25 km² area; check with a provider for this address.At the address

Ontario Energy Board · Innovation, Science and Economic Development Canada

Each record is placed at the distance its own line states. None of it is an inspection of the property. Confirm anything that matters to you with the municipality, Credit Valley Conservationor the record’s publisher.

Contains information licensed under the Open Government Licence – Canada. Contains information licensed under the Open Government Licence – Ontario. Contains information made available under Credit Valley Conservation Open Data Licence v1.0.

The market

Detached homes for sale in Rural Caledon right now

For sale now
160
Median asking price
$1.58M

Middle half: $1.26M to $2.47M

New in 7 days
14

49 in 28 days

Price cuts
14%

22 listings

This home is asking 26% below the median, lower than three quarters of them.

See all homes in Rural Caledon

Asking prices and counts of the MLS® listings on this site as of today. Asking figures only, never sold or leased prices.

Market area · filters apply to the charts below

The street

Schools nearby

ElementaryTypeDistanceEQAO average 2024–25
Glen Williams Public SchoolHalton DSBPublic · grades JK–56.3 km70%Grade 3 average
Alloa Public SchoolPeel DSBPublic · grades JK–86.8 km75%Grade 6 average
Malala Yousafzai PS (Elementary)Peel DSBPublic · grades JK–87.7 km71%Grade 6 average
St. Carlo Acutis Catholic Elementary SchoolDufferin-Peel CDSBCatholic · grades JK–88.6 km—
SecondaryTypeDistanceGrade 9 math 2024–25
Georgetown District High SchoolHalton DSBPublic · grades 9–12 · French Immersion8.4 km72%Grade 9 math
Christ the King Catholic Secondary SchoolHalton CDSBCatholic · grades 9–12 · French Immersion8.7 km58%Grade 9 math
Parkholme Secondary SchoolPeel DSBPublic · grades 9–1210 km—
St Edmund Campion Secondary SchoolDufferin-Peel CDSBCatholic · grades 9–1210 km70%Grade 9 math

EQAO: share of students at or above the provincial standard, 2024–25 (Ontario open data). These are the schools nearest this home, not the schools it is assigned to: boundaries change, and some schools take students by application. Confirm with the board before you buy. Contains information licensed under the Open Government Licence – Ontario.

The verdict

Similar Active Listings

Recently sold nearby

Sold prices in Rural Caledon are shown to signed-in members.

Email Kassaundra Dobson, Broker of Record