Listed for:Listed Jun 29, 2026
$2,500,000

57 Kennedy Road

Caledon (Cheltenham), ON L7C 2M7

Detached House For Sale
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Sale & Price History for 57 Kennedy Road, Caledon, Cheltenham

No listing history available

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About 57 Kennedy Road, Caledon, Cheltenham

Summarized Description

  • Exclusive haven on a secluded 1.88-acre lot.
  • Stunning 2-story great room for entertaining.
  • Luxurious primary suite with five-piece ensuite.
  • Fully finished basement with second kitchen.
  • Private yard with inground pool and cabana.
  • Multiple offices ideal for remote work.
  • Close to local attractions and nature trails.
  • Convenient access to Pearson Airport and Toronto.

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 & Features

Property Costs

Annual Property Tax Amount
$8,025
Land Transfer Tax Fee
$48,975

Rental Items

Rental Equipment
Propane Tank
Under Contract
Propane Tank

Basement Type
Walk-Up, Finished

Interior Features

Laundry Level
Main Level
Interior Extras
Auto Garage Door Remote, Built-In Oven, Countertop Range, Propane Tank, Storage, Trash Compactor, Water Heater Owned
View
Trees/Woods
Fireplace/Stove
Yes
Fireplace Features
Propane
Elevator
No

Exterior Features

Exterior Extras
Privacy, Patio, Landscaped
Pool
Inground
Other Structures
Out Buildings

Building

Building Type
Detached
Building Style
2-Storey
Approx Age
16-30

Construction

Exterior Finish
Brick
Roof
Asphalt Shingle
Foundation Details
Concrete Block
Special Designation
Unknown

Lot

Lot Front
100.00 ft
Lot Depth
753.00 ft
Lot Size
1.88
Lot Shape
Irregular

Inclusions

Inclusions
Fridge, DW, Built in Ovens, Counter Top Range, Trash Compactor, GDO, all ELOs, all pool equipment

Exclusions

Exclusions
Window covering in main floor bedroom, some garden items, BBQ, Patio Lights

Parking & Garages

Garage Type
Attached
Garage Spaces
3
Parking Spaces
9
Total Garage And Parking Spaces
12

Heating & Cooling

Heat Source
Propane
Heat Type
Forced Air
Air Conditioning
Central Air
Water
Well
Sewers
Septic
Hydro
Yes
Cable
Available
Telephone
Available

Bedrooms
4
Washrooms
6
Kitchens
2
Family / bonus room
Yes

Room sizes

  • Kitchen—
    Flat level
  • Recreation—
    Basement level
  • Media Room—
    Basement level
  • Bedroom—
    Flat level
  • Family Room—
    Flat level
  • Bathroom—
    Flat level, 2 Pc Bath
  • Bedroom 3—
    Second level
  • Office—
    Flat level
  • Exercise Room—
    Basement level
  • Great Room—
    Flat level
  • Bedroom 4—
    Second level
  • Kitchen—
    Basement level
  • Bathroom—
    Second level, 4 Pc Ensuite
  • Bathroom—
    Second level, 4 Pc Ensuite
  • Bathroom—
    Second level, 5 Pc Ensuite
  • Primary Bedroom—
    Second level
  • Bathroom—
    Flat level, 3 Pc Bath
  • Laundry—
    Flat level
  • Bathroom—
    Basement level, 2 Pc Bath
  • Office—
    Flat level

Washrooms

  • 5-piece, Second
  • 4-piece, Second
  • 2-piece, Flat
  • 3-piece, Flat
  • 2-piece

Municipality
Caledon
Neighbourhood
Cheltenham
Main cross streets
Creditview & King
Zoning
rr
Directions
Creditview Road to Kennedy Road

MLS® number
W13505786
Data source
Toronto Regional Real Estate Board
Listed on
2026-06-29
Updated on
2026-07-01
Days on market
108 days
Possession type
90+ days
Co-op commission
2.5%
Seller
Listed by
KELLER WILLIAMS EDGE REALTY

Home Market Value

Current home valuation for 57 Kennedy Road, Caledon, Cheltenham, Caledon, ON. Listed for $2,500,000

HOMEH Estimate

?

$2,449,457

Estimated Sales Range

?

$1,469,674 - $3,429,240

HOMEH Estimate for 57 Kennedy Road, Caledon, Cheltenham

Calculated with a real agent's CMA method — 45+ years of experience, codified. Not an AI guess.

$2,449,457Low confidence
Based on 2 comparable properties
+ $50,543 (2%) above our estimate
See the full analysisFree Every recent nearby sale behind this number

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Mortgage Payment Calculator

Compare up to 4 down payment scenarios

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Caledon, ON
Minimum Down Payment Required:20.0%

20% required for homes $1.5M or more

Minimum down payment

$500,000

Scenario 1 Scenario 2 Scenario 3 Scenario 4
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$2,000,000$1,875,000$1,750,000$1,625,000
Amortization
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Payment frequency
=Mortgage payment
$9,765monthly$9,155monthly$8,544monthly$7,934monthly
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Land Transfer Tax

Provincial

$48,975

Total Land Transfer Tax

$48,975

Around this home

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