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Detached for sale at 14451 Winston Churchill Boulevard, Caledon - 4 bedroom, 4 bathroom - Photo 1 of 49
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Detached for sale at 14451 Winston Churchill Boulevard, Caledon - 4 bedroom, 4 bathroom - Photo 9 of 49
Detached for sale at 14451 Winston Churchill Boulevard, Caledon - 4 bedroom, 4 bathroom - Photo 10 of 49
Detached for sale at 14451 Winston Churchill Boulevard, Caledon - 4 bedroom, 4 bathroom - Photo 11 of 49
Detached for sale at 14451 Winston Churchill Boulevard, Caledon - 4 bedroom, 4 bathroom - Photo 12 of 49
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Detached for sale at 14451 Winston Churchill Boulevard, Caledon - 4 bedroom, 4 bathroom - Photo 35 of 49
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Active

$1,900,000

14451 Winston Churchill Blvd

Caledon, ON L7C 1S7

14451 Winston Churchill Blvd, CaledonListed at $1,900,000. 4 bedroom, 4 bathroom 2-Storey. MLS® W13445462.

4Beds
4Baths
3500-5000sqft
2-Storey
25Parking
$4,705 (2025)

What's this home worth?

Get a free estimate for 14451 Winston Churchill Blvd

Description

Escape The Ordinary. Discover Your Private Estate In Prestigious South Caledon Where Sophisticated Country Living Meets Modern Luxury. Nestled On A Breathtaking One-Acre Lot (150X300 Ft), This Newly Extended 4-Bedroom, Over 3,600 Sq Ft Masterpiece Backs Onto A Ravine With Terra Cotta Conservation At Your Doorstep, Privacy And Nature Embrace You At Every Turn. Extensively Renovated Top To Bottom In 2024-All With Permits-This Home Features New Plumbing, Electrical With 200 Amp Service, Septic, Furnace, A/C, Generator, Roof, Doors & Windows Throughout. Designed For Both Grand Entertaining And Intimate Family Living, The Open-Concept Kitchen, Dining & Family Rooms Flow Seamlessly Together. The Brand-New Chef's Kitchen Showcases A Large Island, Stone Counters, Matching Backsplash, And Top-Of-The-Line Stainless Steel Appliances. Large Windows Fill The Home With Natural Light. The Upper-Level Retreat Showcases Two Luxurious Primary Suites. The First Offers A Fireplace, Juliet Balcony Overlooking The Greenspace, Dual Walk-In Closets, And A Spa-Inspired Ensuite Complete With Heated Floors, A Soaker Tub, And An Oversized Glass Shower. The Second Includes Its Own Fireplace, Walk-In Closet, And Heated Ensuite Floors. Ceiling Fans Throughout The Bedrooms And Motorized Blinds Provide Year-Round Comfort, While Convenient Second-Floor Laundry Adds Everyday Ease. Attached Double Garage Plus An Incredible Detached 6-Car Garage/Workshop Offer Endless Possibilities For Car Collectors, Hobbyists, Home Gyms, Or Dream Workspaces. Enjoy A Large Gazebo, Fire Pit Area, And An Unmatched Outdoor Lifestyle. A Rare Opportunity For Families Or Anyone Seeking Space, Privacy, And Refined Country Living Near Town Amenities.

Property Details

Property TypeDetached
Style2-Storey
CommunityRural Caledon
Rooms7
Kitchens1
Washrooms4
Square Feet3500-5000 sqft
Lot Dimensions150.17 × 300.48 ft
Fronting OnWest
Dir/Cross StWinston Churchill Blvd / King St.
Garage TypeAttached
Garage Parking Spaces8
DriveCircular Drive, Private
Parking Drive Spaces17
Total Parking Spaces25
ExteriorStone, Stucco (Plaster)
RoofShingles, Metal
FoundationConcrete Block
BasementCrawl Space
Fireplace FeaturesWood Stove
Heating TypeForced Air
Heating SourcePropane
A/CCentral Air
SewersSeptic
Taxes (2025)$4,705
HSTIncluded In
SecuritySecurity System
Other StructuresAdditional Garage(s), Gazebo
Listed Date6/15/2026
Days on Market34 days
PossessionTBD

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Listing Courtesy of: RE/MAX REALTY SPECIALISTS INC.

MLS® #W13445462

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: 14451 Winston Churchill Boulevard

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

The home offers 4 bedrooms, 4 bathrooms.

Features include a crawl space basement, 25 parking spaces including a 8-car garage, a fireplace.

Additional details: lot dimensions of 150.17 × 300.48 feet.

Listed at $1,900,000 CAD with annual property taxes of $4,705 (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