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Detached for sale at 14294 Winston Churchill Boulevard, Caledon - 4 bedroom, 3 bathroom - Photo 1 of 50
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$1,988,000

14294 Winston Churchill Blvd

Caledon, ON L7C 3E8

14294 Winston Churchill Blvd, Caledon — Listed at $1,988,000. 4 bedroom, 3 bathroom 2-Storey Detached. MLS® W14114964.

Just listed — today

Possession · seller's timeline

Immediate (Immedaite)

4Beds
3Baths
3500-5000sqft
Detached
2-Storey
8Parking
$2,025Taxes/yr · 2025

What's this home worth?

Get a free estimate for 14294 Winston Churchill Blvd

Description

Backing onto protected conservation land with no rear neighbours, this 2.43-acre Terra Cotta estate sits steps from the Cataract 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 backyard is 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.

Property Details

Property TypeDetached
Style2-Storey
CommunityRural Caledon
Approximate Age31-50
Rooms10+2
Kitchens1
Washrooms3
Square Feet3500-5000 sqft
Lot Size2.43 acres (105,851 sq ft)
Lot Dimensions232.35 × 416.18 ft
Lot Size Area2.43 sqft (GeoWarehouse)
Fronting OnWest
Dir/Cross StWinston Churchill Boulevard / King Street
Garage TypeAttached
Garage Parking Spaces2
DrivePrivate Double
Parking Drive Spaces6
Total Parking Spaces8
ExteriorStone, Vinyl Siding
RoofShingles
FoundationConcrete Block
BasementFinished, Full
Fireplace FeaturesPropane, Wood
Heating TypeForced Air
Heating SourcePropane
A/CCentral Air
SewersSeptic
PoolInground, Salt
Taxes (2025)$2,025
HSTIncluded In
SecuritySecurity System, Monitored
Other StructuresFence - Full, Fence - Partial, Other
Listed Date10/25/2026
Days on Market0 days
PossessionImmedaite
Same-day showings available
5.0Rated 5 stars on Google ReviewsWhatsApp Us About This Listing

Property Insights

Home Value
Estimate

Listing Courtesy of: RE/MAX HALLMARK REALTY LTD.

MLS® #W14114964

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: 14294 Winston Churchill Boulevard

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

The home offers 4 bedrooms, 3 bathrooms.

Features include a finished, full basement, 8 parking spaces including a 2-car garage, a fireplace.

Additional details: lot dimensions of 232.35 × 416.18 feet.

Listed at $1,988,000 CAD with annual property taxes of $2,025 (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