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Detached for sale at 17353 Winston Churchill Boulevard, Caledon - 4 bedroom, 5 bathroom - Photo 1 of 3
Detached for sale at 17353 Winston Churchill Boulevard, Caledon - 4 bedroom, 5 bathroom - Photo 2 of 3
Detached for sale at 17353 Winston Churchill Boulevard, Caledon - 4 bedroom, 5 bathroom - Photo 3 of 3
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$2,700,000

17353 Winston Churchill Blvd

Caledon, ON L7K 1N1

17353 Winston Churchill Blvd, Caledon — Listed at $2,700,000. 4 bedroom, 5 bathroom 2-Storey Detached. MLS® W14167074.

Just listed — 2 days ago

Possession · seller's timeline

30-59 days (60 Days)

4Beds
5Baths
3500-5000sqft
Detached
2-Storey
13Parking
$9,438Taxes/yr · 2025
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Description

A custom country retreat in the heart of Terra Cotta. Welcome to 17353 Winston Churchik Boulevard, Caledon, where over 4,000 sq. ft. of living space sits on an approximately 2-acre lot backing onto 15 acres of Crown land. A double-door entry welcomes you to a spacious main f!oor with distinct living, dining, and family rooms, plus a dedicated office or den. The upgraded kitchen features a generous eat-in area with a walkout to a balcony overlooking the natural landscape, an inviting spot for morning coffee or dinner outdoors. Upstairs, you'll find four bedrooms and three full bathrooms, while the finished walkout basement adds a fifth bedroom and an open-concept living area ideal for guests, recreation, or extended family. A three-car garage and driveway parking for more than 10 vehicles make hosting easy. Just minutes from Erin and Belfountain, this custom home offers the space to entertain and the quiet to unwind.

Property Details

Property TypeDetached
Style2-Storey
CommunityRural Caledon
Rooms10
Kitchens1
Washrooms5
Square Feet3500-5000 sqft
Lot Dimensions278.57 × 377 ft
Fronting OnEast
Dir/Cross StWinston Churchill & Bush St
Garage TypeAttached
Garage Parking Spaces3
DrivePrivate
Parking Drive Spaces10
Total Parking Spaces13
ExteriorBrick
RoofAsphalt Shingle
FoundationConcrete
BasementFinished with Walk-Out
Fireplace FeaturesYes
Heating TypeForced Air
Heating SourceGas
A/CCentral Air
SewersSewer
Taxes (2025)$9,438
HSTIncluded In
Listed Date11/10/2026
Days on Market2 days
Possession60 Days
Same-day showings available
5.0Rated 5 stars on Google ReviewsWhatsApp Us About This Listing

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Listing Courtesy of: RE/MAX PRESIDENT REALTY

MLS® #W14167074

TRREBMLS®

The listing data is provided under copyright by the Toronto Regional Real Estate Board (TRREB). The listing data is deemed reliable but is not guaranteed accurate by TRREB. The trademarks REALTOR®, REALTORS®, and the REALTOR® logo are controlled by The Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by CREA and identify the quality of services provided by real estate professionals who are members of CREA. Used under license.

© 2026 Toronto Regional Real Estate Board. All rights reserved.

HouseIndex Take: 17353 Winston Churchill Boulevard

This detached (2-Storey) is located in the Rural Caledon neighbourhood of Caledon.

The home offers 4 bedrooms, 5 bathrooms.

Features include a finished with walk-out basement, 13 parking spaces including a 3-car garage, a fireplace.

Additional details: lot dimensions of 278.57 × 377 feet.

Listed at $2,700,000 CAD with annual property taxes of $9,438 (2025).

About Caledon Real Estate

This Detached is located in the Rural Caledon community in Caledon. Caledon is a vast, scenic municipality in Peel Region spanning the Niagara Escarpment and Oak Ridges Moraine. Bolton is the primary urban centre, while Caledon East and Inglewood offer village living. Popular with buyers seeking acreage, hobby farms, and a rural-meets-suburban lifestyle within commuting distance of Toronto. Detached homes in Caledon are in high demand among families seeking space, privacy, and long-term equity growth.

Niagara Escarpment & Forks of the CreditBolton urban centreHobby farms & rural estate lotsHumber River trails
~60 min commute to downtown TorontoWalkability: Rural — car essential except Bolton core