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Vancor Realty Inc., Brokerage
HouseFor Sale

57 Kennedy Road

Cheltenham, Caledon, ON L7C 2M7

$2,500,000

MLS® 40844026

57 Kennedy Road — photo 1 of 49
1 / 49
  • 4Bedrooms
  • 7Bathrooms
  • 4,415Sq. ft.
  • 12Parking
  • 1998Year built
  • 125Days on market

About this property

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.

Property details

Property

Property type
Single Family Residence
Style
Other
Year built
1998
Lot size
100 x 753 ft
Annual taxes
$8,025
Zoning
RR

Interior

Heating
Fireplace-Propane, Forced Air-Propane
Cooling
Central Air
Basement
Separate Entrance, Walk-Up Access, Full, Finished
Fireplaces
1
Kitchens
2
Included
Range, Trash Compactor, Water Heater Owned, Water Softener, Built-in Microwave, Dishwasher, Dryer, Disposal, Gas Oven/Range, Gas Stove, Refrigerator, Stove, Wine Cooler

Exterior & parking

Construction
Brick
Roof
Asphalt Shing
Foundation
Concrete Block
Garage
3 spaces
Parking spaces
12
Driveway
Private Drive Triple+ Wide
Pool
In Ground

Utilities

Sewer
Septic Tank
Water
Drilled Well, Well

Rooms

RoomLevelSizeFeatures
BathroomBasement—2-Piece
BathroomMain13.05 × 8.13-Piece
Exercise RoomBasement20.03 × 9.11—
OfficeMain13.05 × 10.07French Doors
BathroomMain9 × 62-Piece
StorageBasement10.01 × 8.09—
BathroomSecond8.05 × 6.084-piece, ensuite
BathroomSecond8.05 × 7.114-piece, ensuite
BathroomSecond17 × 165+ piece, ensuite
LaundryMain12 × 7.07—
Bedroom PrimarySecond24.06 × 14.075+ piece, crown moulding
KitchenBasement7.07 × 6.09—
BedroomSecond13.05 × 134-piece, ensuite
BedroomMain14.03 × 13.05—
Media RoomBasement20.06 × 12.1—
BathroomBasement—2-Piece
OfficeMain10.11 × 8.01Hardwood Floor
Family RoomBasement40 × 26.04—
Family RoomMain20 × 13.05bay window, crown moulding
BedroomSecond13.05 × 11.094-piece, ensuite
Great RoomMain30.06 × 22cathedral ceiling(s), fireplace
Eat-in KitchenMain32.03 × 18.02crown moulding, sliding doors
StorageBasement12.1 × 5.06—

Location

57 Kennedy Road, Cheltenham, Caledon, ON, L7C 2M7

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Listing courtesy of Keller Williams Edge Realty. MLS® 40844026. Data provided by Information Technology Systems Ontario (ITSO), last updated September 25, 2026. Information deemed reliable but not guaranteed.

$2,500,000

57 Kennedy Road

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