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Detached for sale at 20040 Kennedy Road, Caledon - 7 bedroom, 4 bathroom - Photo 1 of 41
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Active

$1,799,999

20040 Kennedy Rd

Caledon, ON L7K 1Y3

20040 Kennedy Rd, CaledonListed at $1,799,999. 7 bedroom, 4 bathroom 2-Storey Detached. MLS® W13581702.

7Beds
4Baths
3500-5000sqft
Detached
2-Storey
24Parking
$12,272Taxes/yr · 2025

What's this home worth?

Get a free estimate for 20040 Kennedy Rd

Description

Rare 10 acre estate minutes to Orangeville! Custom Built Home offering 4,100 sq ft above grade andover 6,400 sq ft total living space with 6+ bedrooms, 4 bathrooms, including 2 bedrooms on the main level with their own separate entrance, a full bathroom, and a kitchen offering rental potential,and multi-generational potential. Features include a finished basement with separate entrance, 30x40ft steel workshop with office, C-can with electricity, wood shed, private trails, creek, screened sunroom, theatre room, and oversized garages. Basement layout offers potential to be converted into up to 4 additional bedrooms for rental income, making this a unique opportunity to live, work and unwind in a private country setting.

Property Details

Property TypeDetached
Style2-Storey
CommunityRural Caledon
Rooms12+3
Kitchens2
Washrooms4
Square Feet3500-5000 sqft
Lot Dimensions500.49 × 877.79 ft
Fronting OnWest
Dir/Cross StCharleston Sdrd/Kennedy Rd
Garage TypeAttached
Garage Parking Spaces4
DrivePrivate
Parking Drive Spaces20
Total Parking Spaces24
ExteriorBrick
RoofAsphalt Shingle
FoundationConcrete
BasementFinished, Separate Entrance
Fireplace FeaturesYes
Heating TypeForced Air
Heating SourcePropane
A/CCentral Air
SewersSeptic
Taxes (2025)$12,272
HSTIncluded In
Other StructuresWorkshop
Listed Date7/19/2026
Days on Market16 days
PossessionTBD
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 REALTY SERVICES INC.

MLS® #W13581702

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: 20040 Kennedy Road

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

The home offers 7 bedrooms, 4 bathrooms.

Features include a finished, separate entrance basement, 24 parking spaces including a 4-car garage, a fireplace.

Additional details: lot dimensions of 500.49 × 877.79 feet.

Listed at $1,799,999 CAD with annual property taxes of $12,272 (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