57 Kennedy Road, photo 1

For sale Cheltenham, Caledon, ON

57 Kennedy Road

List price
$2,500,000
Sq ft
3500-5000
Bedrooms
4
Bathrooms
6

About this home

Experience the perfect balance of luxury, nature, and convenience. This property will appeal to the discerning buyer seeking something truly special. Inside 6,500 square feet of thoughtfully blends open-concept living with cozy private retreats. Nestled on a unique, secluded 1.88-acre lot, this is not just another estate - it's an exclusive haven waiting to be yours. Bask in natural light in the stunning 2-story great room flowing seamlessly into the well appointed kitchen that offers space for multiple cooks and seamless entertaining. The 2nd story primary suite is a private retreat, complete with a luxurious five-piece ensuite and a massive walk-in closet. Two additional bedrooms on this floor each feature their own ensuite baths and walk-in closets, ensuring comfort and privacy for family or guests. A fourth bedroom, conveniently located on the main floor, offers its own adjacent 3-piece bath. Need more flexibility? Two main-floor offices provide ideal work-from-home setups or creative spaces. The fully finished walk-up basement is a world of possibilities. With a second kitchen, exercise room, media room, 2-piece bath, and ample storage, it's ready to be transformed into the ultimate entertainment space or in-law suite. Outside is your private paradise, where the lush yard and pool are surrounded by mature trees, offering complete tranquility. A sweeping drive and 3-car garage in the front. An outdoor living space tailored for unforgettable gatherings, featuring an inground pool, a cabana with a 2-piece bath, expansive patios, and deck areas for dining, lounging, and family fun in the back. Beyond the property, the Caledon Trailway, Credit River and the quaint village of Cheltenham are nearby, or explore local gems like Terra Cotta and Belfountain. With Pearson Airport only 30 minutes and downtown Toronto an hour's drive, this property offers countryside living without compromise.

Photos of 57 Kennedy Road

Facts and features of 57 Kennedy Road

Key facts
TypeDetached
Style2-Storey
Bedrooms4
Bathrooms6
Size3500-5000 sq ft
Lot100 x 753 Feet
Parking12
GarageAttached
HeatingForced Air
CoolingCentral Air
BasementWalk-Up, Finished
ExteriorBrick
Age16-30
Taxes$8,025 (2026)
Days on market122
Listing brokerageKELLER WILLIAMS EDGE REALTY

Rooms

20 rooms, with sizes

RoomLevelSizeFeatures
Kitchen Flat 32′ 3″ × 18′ 1″
Recreation Basement 13′ 2″ × 26′ 4″
Media Room Basement 20′ 6″ × 9′ 11″
Bedroom Flat 16′ 1″ × 8′ 9″
Family Room Flat 20′ 0″ × 13′ 5″
Bathroom Flat 9′ 0″ × 6′ 0″ 2 Pc Bath
Bedroom 3 Second 13′ 5″ × 11′ 7″
Office Flat 13′ 5″ × 10′ 7″
Exercise Room Basement 20′ 3″ × 9′ 11″
Great Room Flat 30′ 6″ × 22′ 0″
Bedroom 4 Second 13′ 5″ × 13′ 0″
Kitchen Basement 7′ 7″ × 6′ 9″
Bathroom Second 8′ 5″ × 7′ 11″ 4 Pc Ensuite
Bathroom Second 8′ 5″ × 6′ 8″ 4 Pc Ensuite
Bathroom Second 16′ 0″ × 12′ 3″ 5 Pc Ensuite
Primary Bedroom Second 24′ 6″ × 14′ 11″
Bathroom Flat 13′ 5″ × 8′ 10″ 3 Pc Bath
Laundry Flat 12′ 0″ × 7′ 7″
Bathroom Basement 10′ 1″ × 3′ 2″ 2 Pc Bath
Office Flat 10′ 11″ × 8′ 1″

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MLS® W13505786 Data source: PropTx Listed June 30, 2026