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57 Kennedy Road
Cheltenham Caledon L7C 2M7

$2,500,000
Residential Freehold beds: 4 baths: 6.0

Main Photo: 57 Kennedy Road in Caledon: Cheltenham House for sale : MLS®# W13505786
Photo 1: 57 Kennedy Road in Caledon: Cheltenham House for sale : MLS®# W13505786
Photo 2: 57 Kennedy Road in Caledon: Cheltenham House for sale : MLS®# W13505786
Photo 3: 57 Kennedy Road in Caledon: Cheltenham House for sale : MLS®# W13505786
Photo 4: 57 Kennedy Road in Caledon: Cheltenham House for sale : MLS®# W13505786
Photo 5: 57 Kennedy Road in Caledon: Cheltenham House for sale : MLS®# W13505786
Photo 6: 57 Kennedy Road in Caledon: Cheltenham House for sale : MLS®# W13505786
Photo 7: 57 Kennedy Road in Caledon: Cheltenham House for sale : MLS®# W13505786
Photo 8: 57 Kennedy Road in Caledon: Cheltenham House for sale : MLS®# W13505786
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Photo 12: 57 Kennedy Road in Caledon: Cheltenham House for sale : MLS®# W13505786
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Photo 40: 57 Kennedy Road in Caledon: Cheltenham House for sale : MLS®# W13505786
Photo 41: 57 Kennedy Road in Caledon: Cheltenham House for sale : MLS®# W13505786
Status:
Active
Prop. Type:
Residential Freehold
MLS® Num:
W13505786
Bedrooms:
4
Bathrooms:
6
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.
Under Contract:
Propane Tank
Property Type:
Residential Freehold
Property Sub Type:
Detached
Home Style:
2-Storey
Approx. Age:
16-30
Total Approx Floor Area:
3500-5000
Lot Depth:
753'
Lot Frontage:
100'
Lot Shape:
Irregular
Topography:
Flat
Direction Faces:
South
Bedrooms:
4
Bathrooms:
6.0
Water supply:
Well
Kitchens:
2
Kitchens in Basement:
1
Bedrooms Above Grade:
4
Kitchens Above Grade:
1
Rooms Above Grade:
21
Fractional Ownership:
No
Zoning:
rr
Assignment:
No
Heating type:
Forced Air
Heating Fuel:
Propane
Foundation:
Concrete Block
Roof:
Asphalt Shingle
Basement:
Walk-Up, Finished
Fireplace Features:
Propane
Fireplace/Stove:
Yes
Garage:
Attached
Garage Spaces:
3.0
Other Structures:
Out Buildings
Parking Features:
Private
Parking Spaces:
9
Total Parking Spaces:
12.0
Family Room:
Yes
Possession Details:
90+ days
Pool:
Inground
Link:
No
HST Applicable To Sale Price:
Included In
Assessment:
$817,000
Assessment Year:
2025
Taxes:
$8,024.63 / 2026
Assessment:
$817,000.00 / 2025
Peel
Caledon
Cheltenham
Auto Garage Door Remote, Built-In Oven, Countertop Range, Propane Tank, Storage, Trash Compactor, Water Heater Owned
Privacy, Patio, Landscaped
Propane Tank
Fridge, DW, Built in Ovens, Counter Top Range, Trash Compactor, GDO, all ELOs, all pool equipment
Window covering in main floor bedroom, some garden items, BBQ, Patio Lights
Other
Brick
No
Trees/Woods
Floor
Type
Size
Other
Flat
Great Room
30'6" × 22'
Flat
Kitchen
32'3" × 18'1"
Flat
Family Room
20' × 13'5"
Flat
Bedroom
16'1" × 8'9"
Flat
Office
13'5" × 10'7"
Flat
Office
10'11" × 8'1"
Flat
Laundry
12' × 7'7"
Second
Primary Bedroom
24'6" × 14'11"
Second
Bedroom 3
13'5" × 11'7"
Second
Bedroom 4
13'5" × 13'
Basement
Recreation
26'4" × 13'2¼"
Basement
Exercise Room
20'3" × 9'11"
Basement
Media Room
20'6" × 9'10½"
Basement
Kitchen
7'7" × 6'9"
Floor
Ensuite
Pieces
Other
Flat
No
2
9' x 6' 2 Pc Bath
Flat
No
3
13'5" x 8'10" 3 Pc Bath
Second
Yes
5
16' x 12'3" 5 Pc Ensuite
Second
Yes
4
8'5" x 7'10⅞" 4 Pc Ensuite
Second
Yes
4
8'5" x 6'8" 4 Pc Ensuite
Basement
No
2
10'1" x 3'2" 2 Pc Bath
Utilities Cable:
Available
Utilities Telephone:
Available
Utilities Hydro:
Yes
Utilities Water:
Available
Water Supply Types:
Drilled Well
Energy Certification:
No
Green Property Information Statement:
No
Special Designation:
Unknown
Sewers:
Septic
Air Conditioning:
Central Air
Central Vacuum:
No
Seller Property Info Statement:
No
Physically Handicapped-Equipped:
No
Laundry Level:
Main Level
Date Listed:
Jun 30, 2026
Original Price:
Previous Price:
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Listed by KELLER WILLIAMS EDGE REALTY
Data was last updated July 1, 2026 at 03:15 AM (UTC)
Area Statistics
Listings on market:
10
Avg list price:
$1,714,250
Min list price:
$749,900
Max list price:
$4,399,000
Avg days on market:
31
Min days on market:
11
Max days on market:
293
These statistics are generated based on the current listing's property type and located in Cheltenham. Average values are derived using median calculations. This data is not produced by the MLS® system.
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.