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20040 Kennedy Rd
Caledon, ON L7K 1Y3
20040 Kennedy Rd, Caledon — Listed at $1,799,999. 7 bedroom, 4 bathroom 2-Storey Detached. MLS® W13581702.
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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 Insights
Listing Courtesy of: RE/MAX REALTY SERVICES INC.
MLS® #W13581702


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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).
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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.