57 Kennedy Road

Cheltenham, Caledon, Ontario L7C 2M7

Overview

At a glance

Days on market118 days
ListedJun 30, 2026
UpdatedJun 30, 2026
Building age16-30 years
Size3500-5000 sq ft
Lot100 x 753 Feet
Property taxes$8,025 (2026)
Parking12 spaces
BasementWalk-Up, Finished
MLS® numberW13505786
Data sourcePropTx MLS® System
Listing brokerageKELLER WILLIAMS EDGE REALTY

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.

Details

Property

Style
2-Storey
Building age
16-30
Fronting on
South
Cross street
Creditview & King
Community
Cheltenham
Municipality
Caledon

Inside

Bedrooms above grade
4
Bathrooms
6
Kitchens
2
Basement
Walk-Up, Finished
Family room
Yes
Fireplace
Propane
Interior features
Auto Garage Door Remote, Built-In Oven, Countertop Range, Propane Tank, Storage, Trash Compactor, Water Heater Owned

Utilities

Heating
Forced Air
Heating fuel
Propane
Cooling
Central Air
Water
Drilled Well
Sewer
Septic
Electricity
Yes
Cable
Available

Building

Construction
Brick
Foundation
Concrete Block
Roof
Asphalt Shingle
Exterior features
Privacy, Patio, Landscaped
Pool
Inground

Parking

Garage
Attached
Parking spaces
9
Total parking
12
Driveway
Private

Land

Frontage
100
Depth
753
Lot size units
Feet
Waterfront
No
Topography
Flat
Rooms (20)
RoomLevelSizeFeatures
Great RoomFlat9.3 x 6.71
KitchenFlat9.83 x 5.51
Family RoomFlat6.1 x 4.08
BedroomFlat4.9 x 2.67
OfficeFlat4.09 x 3.23
OfficeFlat3.33 x 2.46
LaundryFlat3.66 x 2.31
BathroomFlat2.74 x 1.832 Pc Bath
BathroomFlat4.09 x 2.693 Pc Bath
Primary BedroomSecond7.47 x 4.55
BathroomSecond4.88 x 3.735 Pc Ensuite
Bedroom 3Second4.09 x 3.53
BathroomSecond2.57 x 2.414 Pc Ensuite
Bedroom 4Second4.09 x 3.96
BathroomSecond2.57 x 2.034 Pc Ensuite
RecreationBasement4.02 x 8.03
Exercise RoomBasement6.17 x 3.02
Media RoomBasement6.25 x 3.01
BathroomBasement3.07 x 0.972 Pc Bath
KitchenBasement2.31 x 2.06
Value

What it’s worth

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Market read

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History

Listing history

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How it compares

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Neighbourhood

Around Cheltenham

What’s nearby

Quiet streetBackyard faces east

  • ParkCheltenham Badlandsabout 20 min walk
  • Playground about 26 min walk
  • TrailCaledon Trailwayabout 1 min walk
  • River or lakeCredit Riverabout 6 min walk
  • Grocery storeBaily's Farm & Marketabout 5.8 km
  • DowntownInglewoodabout 3.9 km
  • LibraryCaledon Public Library - Inglewood Branchabout 4.3 km
  • Rec centre or arenaLloyd Wilson Centennial Arenaabout 3.7 km
  • Golf courseCaledon Golf and Country Clubabout 2.5 km
  • HospitalGeorgetown Hospitalabout 13 km
  • Highway on-rampExit 21about 7.6 km
  • GO or train stationGeorgetownabout 11.8 km

Approximate: straight-line distances, and the backyard and street worked out from the map pin and map data © OpenStreetMap contributors. Check school boundaries with the school board.

On the map

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Community

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Cheltenham sale prices

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Costs

What it would cost

%
%
An example rate. Use the one your lender quotes.
Every monthEstimate
Mortgage payment$0
Property tax$0
Monthly total$0
At closing
Ontario land transfer tax$0

Estimates only, not financial advice. Uses Canadian semi-annual compounding, the minimum down payment and mortgage insurance rules, and Ontario’s land transfer tax brackets. Your lender and lawyer confirm the real numbers. Legal fees, title insurance and moving costs aren’t included.

Listing courtesy of KELLER WILLIAMS EDGE REALTY. Listing information from the PropTx MLS® System. Each listing shows the brokerage that represents it. The information provided herein must only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate and may not be used for any commercial purpose or any other purpose. Information is deemed reliable but is not guaranteed accurate by PropTx. Last updated October 26, 2026 at 4:41 p.m.

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