- Bedrooms
- 4
- Bathrooms
- 6
- Size
- 3,500–5,000sq ft
- Per sq ft
- $588at the range’s middle
- Lot
- 100 x 753 ft
- Tax a year
- $8,0252026 tax year
- Built
- 16-30
- Parking
- 123 attached
- Days on market
- Members
The brief
About 57 Kennedy Rd
57 Kennedy Rd is a 4-bedroom, 6-bathroom detached house in Cheltenham, Caledon, listed for sale at an asking price of $2,500,000 (MLS® W13505786).
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.
Insights
Condition Score
Good68/1006 condition-related facts documented
Source: Listing age, structured features and disclosed update language; not an inspection.
Cashflow Quality
Shortfall5/100−$8,525/mo against the cost of owning (20% down, 4.8%, 25 yrs)
Source: Median of 8 detached homes with 4 bedrooms for lease in Caledon right now. Cost of owning counts the mortgage and property tax.
Condition uses listing-record signals, not an inspection.
The home
Key facts
- Tax
- $8,025 / 2026
- MLS® number
- W13505786
- Board
- TRREB MLS®
- Property Type
- Detached
- Building Age
- 16-30
- Days on market
- Size
- 3500-5000 sqft
- Lot Size
- 100 x 753 ft
- Listed on
- Parking
- 3 Attached, 12 Parking
Property details
Property
- Property Type
- Detached
- Style
- 2-Storey
- Community
- Cheltenham
- Municipality
- Caledon
Building
- Size
- 3500-5000 sqft
- Building Age
- 16-30
- Construction
- Brick
Inside
- Bedrooms
- 4
- Bathrooms
- 6
- Bathroom Details
- 1 × 5pc 2nd, 2 × 4pc 2nd, 1 × 2pc Flat, 1 × 3pc Flat, 1 × 2pc
- Basement Type
- Walk-Up
- Kitchens
- 1
Parking
- Driveway
- Private
- Garage Type
- Attached
- Garage
- 3
- Additional Parking
- 9
- Total Parking
- 12
Utilities
- Water
- Well
- Cooling
- Central Air
- Heating Type
- Forced Air
Land
- Sewer
- Septic
- Frontage
- 100 ft
- Depth
- 753 ft
- Lot Size
- 100 x 753 ft
Additional
- Foundation
- Concrete Block
- Roof
- Asphalt Shingle
- Fireplace
- Yes
- Pool
- Inground
- Den
- Yes
- Family room
- Yes
- Extras
- Fridge, DW, Built in Ovens, Counter Top Range, Trash Compactor, GDO, all ELOs, all pool equipment
Rooms
| Room | Size | Features | Level |
|---|---|---|---|
| Great Rm | 6.71 × 9.3 m | — | Flat |
| Kitchen | 5.51 × 9.83 m | — | Flat |
| Family | 4.08 × 6.1 m | — | Flat |
| Br | 2.67 × 4.9 m | — | Flat |
| Office | 3.23 × 4.09 m | — | Flat |
| Office | 2.46 × 3.33 m | — | Flat |
| Laundry | 2.31 × 3.66 m | — | Flat |
| Bathroom | 1.83 × 2.74 m | 2 Pc Bath | Flat |
| Bathroom | 2.69 × 4.09 m | 3 Pc Bath | Flat |
| Primary | 4.55 × 7.47 m | — | 2nd |
| Bathroom | 3.73 × 4.88 m | 5 Pc Ensuite | 2nd |
| 3rd Br | 3.53 × 4.09 m | — | 2nd |
| Bathroom | 2.41 × 2.57 m | 4 Pc Ensuite | 2nd |
| 4th Br | 3.96 × 4.09 m | — | 2nd |
| Bathroom | 2.03 × 2.57 m | 4 Pc Ensuite | 2nd |
| Rec | 8.03 × 4.02 m | — | Bsmt |
| Exercise | 3.02 × 6.17 m | — | Bsmt |
| Media/Ent | 3.01 × 6.25 m | — | Bsmt |
| Bathroom | 0.97 × 3.07 m | 2 Pc Bath | Bsmt |
| Kitchen | 2.06 × 2.31 m | — | Bsmt |
Listing history
Buy/sell history for 57 Kennedy Rd, Caledon, Ontario
Sale history on this site covers the last 2 years, the window permitted under the TRREB MLS® VOW agreement.
| Date Start | Date End | List Price | Price | Event | Listing ID |
|---|---|---|---|---|---|
| Date StartN/A | N/A | $2,500,000 | N/A | For Sale | W13505786 |
Members see the full history. Prices are hidden from signed-out visitors.
The numbers
Mortgage Calculator
Plan with the current asking price
CMHC insurance: not required at 20% down. Payments use Canadian semi-annual compounding.
Mortgage Details
4.8% · 5-year term · 25-year amortization · 20% down
- Total down payment
- $500,000
- Total mortgage amount
- $2,000,000
- Total interest payment
- $1,421,800
- Total purchase cost
- $3,921,800
- Mortgage payment
- $11,406/mo
Cash Flow Analysis
If you rented this home out at 20% down
Break-even down payment
80%Monthly carrying cost
$12,075- Rent $3,550
- Shortfall $8,525
Rental income opens at $3,550, the median asking rent of 8 comparable homes for lease in Caledon. Type over it with the rent you expect. This is a planning tool, not advice.
Land transfer tax on this home
- Ontario land transfer tax
- $48,975
- Total land transfer tax
- $48,975
- First-time buyer rebates (Ontario up to $4,000)
- −$4,000
- Total for first-time buyers
- $44,975
See how this is worked out
- 0.5% on the first $55,000
- $275
- 1.0% from $55,000 to $250,000
- $1,950
- 1.5% from $250,000 to $400,000
- $2,250
- 2.0% from $400,000 to $2,000,000
- $32,000
- 2.5% from $2,000,000 to $2,500,000
- $12,500
- Ontario total
- $48,975
An estimate at the asking price, for a home with one or two single-family residences. Your lawyer confirms the exact amount.
Estimate
Estimated value requires sign in
Market estimates use sold comparables and are available after you sign in and accept MLS® VOW terms.
The estimate is an automated value built from public and MLS® data. It is not an appraisal; ask Kassaundra Dobson, Broker of Record for a full comparative market analysis.
Comparable sales
Comparable sales require sign in
Closing prices and sold comps are available to registered visitors who accept MLS® VOW terms on this site.
The land
Lot
- Street frontage
- 100 ft30.5 m
- Depth
- 753 ft229.5 m
The record marks this lot irregular, so its area is not the frontage multiplied by the depth. It is not given here. Confirm with a survey before you buy.
Source: the MLS® listing record, measured by MPAC.
Land and environment
Public records about this location. Not part of the MLS® listing and not provided by the listing brokerage.
Water and conservation5
- Not in Credit Valley Conservation’s mapped regulated areaAt the address
- No mapped wetland within 120 m120 m
- 18 water-supply wells recorded within 250 mAll were drilled for domestic use. From Ontario’s well records; locations can be approximate. The records do not show how this home gets its water. Wells nearby typically go down about 19.2 m.250 m
- Groundwater recorded about 6.1 m below ground nearbyThe middle water level in the well records within 500 m (82 records). It changes with the season and from spot to spot.500 m
- Bedrock about 6.1 m down nearbyThe middle depth to bedrock in the well records within 500 m.500 m
Credit Valley Conservation · Province of Ontario open data
Planning and building activity2
- Inside the Greenbelt (Niagara Escarpment Plan) and the Niagara Escarpment plan area (Escarpment Rural Area)These provincial plans set policies on new buildings, new lots and some changes to the land; the municipality can say which apply to this property.At the address
- Nearest airport: 3.6 km3.6 km
Province of Ontario open data
Around the home2
- Nearest rail line: 810 m810 m
- A trail on the Ontario trail network within 1 km1 km
Province of Ontario open data
Environmental records4
- 2 licensed pits or quarries within 2 kmThe nearest is 690 m away, as mapped.2 km
- No recorded oil, gas or salt well within 250 m250 m
- No facility within 1 km reports pollutant releases to Environment CanadaOnly facilities above the inventory’s reporting thresholds are listed.1 km
- No federal contaminated site within 1 kmThe federal inventory covers federal land only; it says nothing about provincial or private sites.1 km
Province of Ontario open data · Government of Canada open data
Power and internet3
- Electricity is distributed here by Hydro One Networks Inc.At the address
- Wired internet 50/10 Mbps or faster is listed at a household 110 m awayFixed wireless 50/10 Mbps or faster. LTE mobile coverage listed. ISED’s National Broadband Data at the nearest household point (110 m from the listing); 50/10 Mbps is its top category and includes faster plans. Confirm with a provider for this address.110 m
- Across the surrounding area: fibre to the home, cable, DSL internet listedFibre to the home: Bell, NFTC. Cable: Rogers. DSL: Bell. Fixed wireless: Bell, Rogers, Routcom, SkyChoice Communications, Standard Broadband, Vianet. Mobile: Bell, Freedom Mobile, Rogers, Telus. Satellite: Xplore. ISED’s list for the surrounding ~25 km² area; check with a provider for this address.Area-wide
Ontario Energy Board · Innovation, Science and Economic Development Canada
Each record is placed at the distance its own line states. None of it is an inspection of the property. Confirm anything that matters to you with the municipality, Credit Valley Conservationor the record’s publisher.
Contains information licensed under the Open Government Licence – Canada. Contains information licensed under the Open Government Licence – Ontario. Contains information made available under Credit Valley Conservation Open Data Licence v1.0.
The market
Detached homes for sale in Cheltenham right now
- For sale now
- 5
- Median asking price
- $2.5M
- New in 7 days
- 0
- Price cuts
- 0%
Middle half: $900K to $2.9M
1 in 28 days
0 listings
This home is asking at the median.
See all homes in CheltenhamAsking prices and counts of the MLS® listings on this site as of today. Asking figures only, never sold or leased prices.
Market area · filters apply to the charts below
The street
Map and tour
Schools nearby
| Elementary | Type | Distance | EQAO average 2024–25 |
|---|---|---|---|
| Herb Campbell Public SchoolPeel DSB | Public · grades JK–8 · French Immersion | 6 km | 79%Grade 6 average |
| Tony Pontes (Elementary)Peel DSB | Public · grades JK–8 | 7.3 km | 72%Grade 6 average |
| St. Evan Catholic Elementary SchoolDufferin-Peel CDSB | Catholic · grades JK–8 | 8.6 km | 68%Grade 6 average |
| ÉÉC Saint-Jean-BoscoConseil scolaire catholique MonAvenir | French-language Catholic · grades JK–6 | 9 km | 72%Grade 6 average |
| Secondary | Type | Distance | Grade 9 math 2024–25 |
|---|---|---|---|
| Parkholme Secondary SchoolPeel DSB | Public · grades 9–12 | 10 km | — |
| Fletcher's Meadow Secondary SchoolPeel DSB | Public · grades 9–12 | 11 km | 40%Grade 9 math |
| St Edmund Campion Secondary SchoolDufferin-Peel CDSB | Catholic · grades 9–12 | 11 km | 70%Grade 9 math |
| Erin District High SchoolUpper Grand DSB | Public · grades 9–12 · French Immersion | 11 km | 61%Grade 9 math |
EQAO: share of students at or above the provincial standard, 2024–25 (Ontario open data). These are the schools nearest this home, not the schools it is assigned to: boundaries change, and some schools take students by application. Confirm with the board before you buy. Contains information licensed under the Open Government Licence – Ontario.
The verdict
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Sold prices in Cheltenham are shown to signed-in members.