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.
Key Facts:
Tax:
$8,025 / 2026
Property Type:
Detached
Building Age:
16-30 years
Sq. ft. size
3500-5000 sq. ft.
Lot Size:
100 x 753 feet
Lot Irregularities:
PT LT 31 CON 3 WHS CHINGUACOUSY AS IN RO983920 ; CALEDON
Parking:
Attached garage (3), 12 spaces in total
Basement:
Walk-Up, Finished
Listing #:
W13505786
Days on Site:
128 days
Status Change:
126 days ago
Added to CiRealty:
2026-06-30
Updated on:
2026-06-30
Market Demand:
Buyer’s Market
Balanced
Seller’s Market
Property Details
Property details for 57 Kennedy Rd, Caledon. Listed for $2,500,000 on 2026-06-30
Property
Property Type:
Detached
Style:
2-Storey
Community:
Cheltenham
Municipality:
Caledon
Inside
Bedrooms:
4
Bathrooms:
6
Bathrooms Detail:
1 × 5pc, 2nd floor
Bathrooms Detail:
2 × 4pc, 2nd floor
Bathrooms Detail:
1 × 2pc, flat
Bathrooms Detail:
1 × 3pc, flat
Bathrooms Detail:
1 × 2pc
Kitchens:
1 + 1
Rooms:
21
Family Room:
Yes
Den:
Yes
Fireplace:
Yes
Central Vac:
No
Utilities
Water:
Well
Cooling:
Central Air
Heating Type:
Forced Air
Building
Size:
3500-5000 sq. ft.
Building Age:
16-30 years
Construction:
Brick
Parking
Garage Type:
Attached
Garage Spaces:
3
Driveway:
Private
Driveway Spaces:
9
Total Parking Spaces:
12
Land
Sewer:
Septic
Frontage:
100 feet
Depth:
753 feet
Cross Street:
Creditview & King
Property
Property Type:
Detached
Style:
2-Storey
Community:
Cheltenham
Municipality:
Caledon
Building
Size:
3500-5000 sq. ft.
Building Age:
16-30 years
Construction:
Brick
Parking
Garage Type:
Attached
Garage Spaces:
3
Driveway:
Private
Driveway Spaces:
9
Total Parking Spaces:
12
Inside
Bedrooms:
4
Bathrooms:
6
Bathrooms Detail:
1 × 5pc, 2nd floor
Bathrooms Detail:
2 × 4pc, 2nd floor
Bathrooms Detail:
1 × 2pc, flat
Bathrooms Detail:
1 × 3pc, flat
Bathrooms Detail:
1 × 2pc
Kitchens:
1 + 1
Rooms:
21
Family Room:
Yes
Den:
Yes
Fireplace:
Yes
Central Vac:
No
Land
Sewer:
Septic
Frontage:
100 feet
Depth:
753 feet
Cross Street:
Creditview & King
Utilities
Water:
Well
Cooling:
Central Air
Heating Type:
Forced Air
Rooms
Room details for 57 Kennedy Rd, Caledon. (Listed for $2,500,000 on 2026-06-30)
Great Rm (30'6" x 22'0")
Kitchen (32'3" x 18'1")
Family (20'0" x 13'5")
Br (16'1" x 8'9")
Office (13'5" x 10'7")
Office (10'11" x 8'1")
Laundry (12'0" x 7'7")
Bathroom (9'0" x 6'0")
2 Pc Bath
Bathroom (13'5" x 8'10")
3 Pc Bath
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