57 Kennedy Road, Caledon, ON

$2,500,000
MLS#:W13505786
4 beds
6 baths
3500-5000 sqft
12.0 parking
Residential Freehold
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Added:Jun 29, 2026(61 days ago)
Updated:Jul 1, 2026(59 days ago)
Last Checked:6 minutes ago

Property Highlights

Welcome to this remarkable 2-Storey detached located in the coveted neighborhood of Cheltenham. Expertly crafted featuring premium brick construction, this residence presents an exceptional opportunity offered at $2,500,000 to acquire a beautiful home in a highly sought-after setting. Designed for both comfortable daily living and elegant entertaining, the layout maximizes natural light, functional flow, and lifestyle utility.

  • 4 Bedrooms and 6 Bathrooms with 2 functional kitchens
  • Generous living space spanning 3500-5000 sqft on a premium 100 x 753 ft lot
  • Features a walk-up, finished basement, adding superb versatility for recreation, a home gym, or extra storage
  • 12.0 total parking spaces available with a convenient attached configuration
  • Notable attributes: Auto Garage Door Remote, Built-In Oven, Countertop Range
  • equipped with central air central cooling and highly efficient forced air heating via propane

Description

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.

Work with the SOUSA TEAM to unlock your . If we are unable to negotiate your purchase price below asking, we'll rebate you up to $10,000!*

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Property Summary

This detached home located at 57 Kennedy Road, Caledon is currently for sale and has been available on SousaSells for 61 days. This property is listed at $2,500,000 with an estimated mortgage of $8,322* per month. It has 4 beds, 6 bathrooms, and is 3500-5000 square feet. 57 Kennedy Road, Caledon is in the Cheltenham neighborhood.

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* Estimated mortgage assumes a 30% down payment, 4.00% interest rate, and 30-year amortization.
Is this a Good Home for Families?

Yes! Featuring 4 bedrooms and 6 bathrooms, this home offers ample space and comfort for growing families in Cheltenham, Caledon.

Highly Recommended for Families
What We Love About This Home
  • •4 spacious bedroom layout offering versatile living space
  • •6 well-appointed bathrooms
  • •3500-5000 sqft of generous functional square footage
Standout Features & Layout
Who Should Buy This Home?

Growing families needing multi-bedroom flexibility and space in Cheltenham, Caledon.

Target Buyer Match

Key Features

Bedrooms
4
Bathrooms
6
Kitchens
2
Living Area
3500-5000 sqft
Property Type
Residential Freehold

Additional Details

StatusActive
AddedJun 29, 2026 (61 days ago)
UpdatedJul 1, 2026 (59 days ago)
Last Checked6 minutes ago
Transaction TypeFor Sale

Property Details

Property Sub-TypeDetached
Architectural Style2-Storey
ConstructionBrick
BasementWalk-Up, Finished
Lot Size100 × 753 Feet
CountyPeel
Annual Tax$8,024.63
Legal DescriptionPT LT 31 CON 3 WHS CHINGUACOUSY AS IN RO983920 ; CALEDON

Parking & Garage

Parking Total12.0
Parking Space9
Garage TypeAttached

Heating & Cooling

Heat SourcePropane
Heat TypeForced Air
CoolingCentral Air

Features

Property Features

None listed

Interior Features

  • Auto Garage Door Remote
  • Built-In Oven
  • Countertop Range
  • Propane Tank
  • Storage
  • Trash Compactor
  • Water Heater Owned

Security Features

None listed

Community Features

None listed

Frequently Asked Questions about 57 Kennedy Road, Caledon, ON

Q.What is the asking price for 57 Kennedy Road, Caledon, ON ?

The current listing price for 57 Kennedy Road, Caledon, ON in Cheltenham, Caledon is $2,500,000.

Q.How many bedrooms and bathrooms does this property have?

This property features 4 bedrooms and 6 bathrooms across approximately 3500-5000 sqft.

Q.What property type and architectural style is 57 Kennedy Road, Caledon, ON ?

57 Kennedy Road, Caledon, ON is a Detached (2-Storey) featuring a Walk-Up, Finished basement.

Q.What interior features are included in this home?

Interior highlights include: Auto Garage Door Remote, Built-In Oven, Countertop Range, Propane Tank, Storage, Trash Compactor, Water Heater Owned.

Q.Is parking available at this property?

Yes, this property offers parking space for 12.0 vehicles (Attached).

Q.What heating and cooling systems are installed?

Heating is provided via Propane and cooling via Central Air.

Virtual Tour & 3D Walkthrough

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Location

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57 Kennedy Road, Caledon, ON

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Neighborhood Safety Index

Neighborhood Safety & Crime Analytics

Cheltenham, Caledon

SAFETY RATING9.8 / 10
Low Incident Area
Total Annual Incidents9 incidents / yr
Average Per Month0.8 incidents / mo
Population Benchmark5,000 residents
Personal Safety
Very Low

2 assaults (40.0/100k)

Property Security
Very Low

2 B&E (40.0/100k)

Auto Theft Risk
Moderate

3 thefts (60.0/100k)

1-Year Trend
â–¼ 9%

Improving vs previous year

How Per-Capita Rate (Per 100,000 Residents) Is Calculated:

Formula: (Annual Occurrences / Population) × 100,000. This standard policing calculation normalizes incident frequencies across different population sizes, allowing accurate safety comparisons between quiet residential pockets and dense urban centres.

Source: Peel Regional Police (PRP) Open Data
Halton & GTHA Police Network

Disclaimer: Crime and safety analytics are compiled from official municipal and regional police open data records for general consumer informational and demographic research purposes only. Data is deemed reliable but is not guaranteed and does not constitute a legal representation or guarantee of future safety.

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Property History

No historical data available for this property.

This could be the first listing for this address.

Pricing & Value Insights

Data-driven valuation for 57 Kennedy Road, Caledon, ON L7C 2M7

Estimated Sales Range
$1.2M - $1.4M

Based on 0 recent similar sales in the pocket.

Market Speed
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Properties in this area are selling at a steady pace.

Market Trend
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Mortgage & Affordability Audit

Calculate your monthly payment, minimum downpayment, and land transfer taxes for this home in Caledon.

Configure Loan Settings

Interest Rate4.00%
Down Payment$750,000 (30.0%)
* Minimum Canadian down payment required for this price is $500,000.
Amortization Period30 Years
Estimated Monthly Payment$8,322Based on a loan of $1,750,000 over 30 years.
Purchase Price$2,500,000
Loan Amount$1,750,000
Provincial Land Transfer Tax:$48,975
Total Estimated Closing Taxes:$48,975

About Purchasing a Home in Caledon, ON

For a property listed at $2,500,000 in Caledon, the legal minimum down payment is $500,000 under current Canadian banking regulations. This calculation applies a 5% requirement on the first $500,000, 10% on the next $499,999, and a flat 20% on any amount exceeding $1,000,000.

Additionally, buyers in Ontario must budget for the Provincial Land Transfer Tax, which is estimated at $48,975 for this transaction. As this listing is in Caledon (outside the City of Toronto), no additional municipal land transfer tax is levied, resulting in total estimated land transfer taxes of $48,975.

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Cheltenham, Caledon Neighborhood Guide

Comprehensive city-wide demographics, local real estate stats, and school rankings for Cheltenham, Caledon.

Verified Local Data
City Population6,202,225
City Median Age39.6 Yrs
City Ownership65% Owners
Avg Area List Price$1,903,287

People & Families

Age Distribution

Household Composition

One-person households
25%
Families with children
50%
Couples without children
24%
Other households
0%

Top Ethnic Origins

Chinese11%
English9%
Indian9%
Irish8%

Best Schools in Cheltenham, Caledon

Elementary Schools

Macville
PublicBolton, Ontario, L7C 0S3
9.6
Alton
Public19681 Main Street, Alton, Caledon, Ontario, L7K 0E1
7.9
SouthFields Village
Public110 Learmont Avenue, Mayfield West, Caledon, Ontario, L7C 3R1
6.7
St. Evan
Catholic500 Dougall Avenue, Mayfield West, Caledon, Ontario, L7C 4C6
6.3
Saint-Jean-Bosco
Public55 Abbotside Way, Mayfield West, Caledon, Ontario, L7C 4C3
5.8

Secondary Schools

Mayfield SS
PublicBrampton, Ontario, L6P 2Z9
7.2

Cheltenham, Caledon Demographic Home information

Structural Home Types

Tenure (Ownership vs Rental)

Owner-Occupied65%
Rented35%

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Notice: Market Insights are generated by analyzing real-time data and should be used for informational purposes only. Consult with a licensed professional for exact valuations.

Disclaimer: AI Insights are generated by an automated system and should be used for informational purposes only. While we strive for accuracy using current market data and deep-learning models, these assessments do not constitute professional real estate, legal, or financial advice. All property values, predictions, and scores are estimates. We strongly recommend verifying all property details and conducting independent due diligence with a licensed professional before making any purchase decisions.

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