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Caledon, King, Toronto, New Tecumseth & Orangeville(437) 228-3434
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MLS® C13797004For SaleDetached

21 Fifeshire Rd

St. Andrew-Windfields, Toronto, Ontario M2L 2G4

Map
1 / 40
21 Fifeshire Rd, Toronto, photo 1
Asking$6,995,000
Bedrooms
5+1
Bathrooms
8
Size
5,000 +sq ft
Lot
121.89 x 178.36 ft
Tax a year
$23,3772025 tax year
Parking
142 built-in
Days on market
Members

The brief

About 21 Fifeshire Rd

21 Fifeshire Rd is a 5+1-bedroom, 8-bathroom detached house in St. Andrew-Windfields, Toronto, listed for sale at an asking price of $6,995,000 (MLS® C13797004).

Bespoke Residence Set On A Stunning 121' Wide Manicured Lot Which Stands Among The Finest In Prestigious Estates On The Much Sought After St. Andrew-Windfields Neighborhood. Encompassing Approximately 8,300 Square Feet Of Curated Living Space With Ideal Entertainment Flow, The Residence Is Defined By Imported Marble, Rich Hardwood, Tailored Lighting, And Refined Designer Detailing Throughout. Beyond A Tree-Lined Circular Drive, The Stately 6+1 Bedroom, 9 Bathroom Home Reveals A Grand Foyer Of Striking Elegance, Where A Soaring Cathedral Ceiling With Skylight Bathes The Interiors In Natural Light, Accentuating A Sweeping Natural Stone Staircase With Custom Brass And Wrought Iron Railings. Gracious Formal Living And Dining Rooms, Alongside A Distinguished Library Adorned In Brazilian Redwood, And A Custom Chef's Kitchen, Anchor The Main Level With Timeless Sophistication. A Charming Breakfast Area And Expansive Family Room Seamlessly Extend To The Rear Garden Oasis, Creating An Effortless Setting For Both Intimate Gatherings And Entertaining. The Primary Retreat Is A Sanctuary Unto Itself, Featuring A Tranquil Sitting Area With A Custom Fireplace, His And Hers Walk-In Closets, And Accompanying His-And-Hers Ensuites. Five Additional Bedrooms Complete The Second Level. The Lower Level Offers An Exceptional Extension Of Living Space, Including A Nanny Suite, Oversized Recreation Room, Full Bar, Exercise Room With Ensuite Sauna, Cedar Closet, And A Walk-Up To The Gardens, With Ample Opportunity For Further Customization. Outdoors, The Estate Impresses With A 20' X 40' Pool, Multiple Lounging And Entertaining Areas, An Expansive Stone Terrace, And A Serene Koi Pond, All Enveloped By Lush Landscaping To Ensure Ultimate Privacy. A Rare And Distinguished Offering In One Of The City's Most Coveted Enclaves.

Insights

  • Condition Score

    Good

    6 condition-related facts documented

    Source: Listing age, structured features and disclosed update language; not an inspection.

  • Cashflow Quality

    Shortfall

    −$26,861/mo against the cost of owning (20% down, 4.8%, 25 yrs)

    Source: Median of 49 detached homes with 6 bedrooms for lease in Toronto right now. Cost of owning counts the mortgage and property tax.

Condition uses listing-record signals, not an inspection.

The home

Key facts

Tax
$23,377 / 2025
MLS® number
C13797004
Board
TRREB MLS®
Property Type
Detached
Days on market
Size
5000 + sqft
Lot Size
121.89 x 178.36 ft
Listed on
Parking
2 Built-In, 14 Parking
Listing brokerage: RE/MAX REALTRON BARRY COHEN HOMES INC.Data source: TRREB MLS®Information deemed reliable but not guaranteed. Contained information is subject to errors, omissions, and changes without notice. Information should be independently verified.

Property details

Property

Property Type
Detached
Style
2-Storey
Community
St. Andrew-Windfields
Municipality
Toronto

Building

Size
5000 + sqft
Construction
Stucco/Plaster

Inside

Bedrooms
5+1
Bathrooms
8
Bathroom Details
1 × 2pc, 2 × 5pc, 1 × 6pc, 2 × 4pc, 2 × 4pc
Basement Type
Walk-Up
Kitchens
1

Parking

Driveway
Circular
Garage Type
Built-In
Garage
2
Additional Parking
12
Total Parking
14

Utilities

Water
Municipal
Cooling
Central Air
Heating Type
Forced Air

Land

Sewer
Sewers
Frontage
121.89 ft
Depth
178.36 ft
Lot Size
121.89 x 178.36 ft

Additional

Foundation
Concrete
Roof
Shingles
Fireplace
Yes
Pool
Inground
Den
Yes
Family room
Yes
Extras
Paul Bocuse 4-Burner Gas Range Plus Griddle And Double Oven, Hood Fan, Sub-Zero Fridge, Sub-Zero Freezer, KitchenAid Dishwasher, Panasonic Speed Oven, LG Washer/Dryer, All Elfs, and Window Covs

Rooms

RoomSizeFeaturesLevel
Foyer3.53 × 9.6 mMarble Floor, Double Closet, Crown MouldingMain
Living3.94 × 9.6 mhardwood floor, Picture Window, O/Looks FrontyardMain
5th Br3.3 × 4.27 mDouble Closet, hardwood floor, Combined W/Sitting2nd
Kitchen4.04 × 4.47 mBreakfast Area, Centre Island, Marble FloorMain
Dining3.94 × 4.5 mBay Window, Crown Moulding, O/Looks LivingMain
Br3.89 × 4.34 m3 Pc Ensuite, Pot Lights, ClosetLower
Family4.47 × 7.52 mW/O To Terrace, Skylight, FireplaceMain
3rd Br3.94 × 4.9 mCloset, O/Looks Backyard, hardwood floor2nd
2nd Br4.04 × 6.53 mhardwood floor, Double Closet, O/Looks Frontyard2nd
Rec3.81 × 11.35 mWet Bar, Fireplace, Above Grade WindowLower
4th Br3.15 × 3.3 mhardwood floor, O/Looks Garden, Double Closet2nd
Office5.33 × 6.5 mFireplace, O/Looks Frontyard, hardwood floorMain
Primary5.28 × 12.7 m5 Pc Ensuite, W/I Closet, Combined W/Sitting2nd

Listing history

Buy/sell history for 21 Fifeshire Rd, Toronto, Ontario

Sale history on this site covers the last 2 years, the window permitted under the TRREB MLS® VOW agreement.

Date StartDate EndList PricePriceEventListing ID
Date StartN/AN/A$6,995,000N/AFor SaleC13797004

Members see the full history. Prices are hidden from signed-out visitors.

The numbers

Mortgage Calculator

Plan with the current asking price

20% · $1,399,000

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
$1,399,000
Total mortgage amount
$5,596,000
Total interest payment
$3,977,900
Total purchase cost
$10,972,900
Mortgage payment
$31,913/mo

Cash Flow Analysis

If you rented this home out at 20% down

Break-even down payment

87%

Monthly carrying cost

$33,861
−$26,861per month
  • Rent $7,000
  • Shortfall $26,861

Rental income opens at $7,000, the median asking rent of 49 comparable homes for lease in Toronto. 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
$161,350
Toronto municipal land transfer tax
$251,200
Total land transfer tax
$412,550
First-time buyer rebates (Ontario up to $4,000 + Toronto up to $4,475)
−$8,475
Total for first-time buyers
$404,075
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 $6,995,000
$124,875
Ontario total
$161,350

Toronto’s municipal tax has its own higher brackets at this price, so it adds $251,200.

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
121.89 ft37.2 m
Depth
178.36 ft54.4 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.

15 records · 7 on fileRead 2026-11-04
250 m500 m1 km2 kmBeyond · area-wideNot in Toronto and Region Conservation Authority’s mapped regulated areaNo mapped wetland within 120 mNo water-supply well recorded within 250 mOutside the Greenbelt, Oak Ridges Moraine and Niagara Escarpment plan areasMapped parcel: about 16,150 sq ft4 building permits issued within 250 m in the last 2 yearsNearest airport: 5.3 kmA trail on the Ontario trail network within 1 kmNo licensed pit or quarry within 2 kmNo recorded oil, gas or salt well within 250 mNo facility within 1 km reports pollutant releases to Environment CanadaNo federal contaminated site within 1 kmElectricity is distributed here by Toronto Hydro-Electric System LimitedWired internet 50/10 Mbps or faster is listed at a household 30 m awayAcross the surrounding area: fibre to the home, cable, DSL internet listed
On record Checked, none on record

Water and conservation3

  • Not in Toronto and Region Conservation Authority’s mapped regulated areaAt the address
  • No mapped wetland within 120 m120 m
  • No water-supply well recorded within 250 m1 test or monitoring hole also recorded.250 m

Toronto and Region Conservation Authority · Province of Ontario open data

Planning and building activity4

  • Outside the Greenbelt, Oak Ridges Moraine and Niagara Escarpment plan areasAt the address
  • 4 building permits issued within 250 m in the last 2 years250 m
  • Nearest airport: 5.3 km5.3 km
  • Mapped parcel: about 16,150 sq ftMeasured from the municipal parcel map, which can differ from the survey and from the lot size in the listing.At the address

Province of Ontario open data · Municipal building permits · toronto.parcels

Around the home1

  • A trail on the Ontario trail network within 1 km1 km

Province of Ontario open data

Environmental records4

  • No licensed pit or quarry within 2 km2 km
  • No recorded oil, gas or salt well within 250 m250 m
  • No facility within 1 km reports pollutant releases to Environment CanadaThe nearest is Vishay Precision Group Canada ULC (KELK), 2.7 km away. Only 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 Toronto Hydro-Electric System LimitedAt the address
  • Wired internet 50/10 Mbps or faster is listed at a household 30 m awayFixed wireless 50/10 Mbps or faster. LTE mobile coverage listed. ISED’s National Broadband Data at the nearest household point (30 m from the listing); 50/10 Mbps is its top category and includes faster plans. Confirm with a provider for this address.30 m
  • Across the surrounding area: fibre to the home, cable, DSL internet listedFibre to the home: Beanfield Metroconnect, Bell, CIK Telecom, FibreStream. Cable: Rogers. DSL: Bell. Fixed wireless: Rogers, Routcom, SkyChoice Communications. 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, Toronto and Region Conservation Authorityor the record’s publisher.

Contains information licensed under the Open Government Licence – Canada. Contains information licensed under the Open Government Licence – Ontario. Contains information licensed under the Open Government Licence – Toronto. Contains information made available under the Toronto and Region Conservation Authority Open Data Licence v1.0.

Heritage and ravine protection

  • Not found on the Heritage Register
  • Not in a mapped Heritage Conservation District
  • Not in the mapped ravine protection area

What this means: None of these City records was found at this address. That does not rule out other approvals, such as a conservation authority permit, so check before you plan work.

City of Toronto Heritage Register, Heritage Conservation Districts and the Ravine and Natural Feature Protection by-law, read at this address from the City’s maps. Contains information licensed under the Open Government Licence – Toronto.

Zoning

Zone

RD (f30.0; a1850) (x975)

By-law

569-2013

Municipality

Toronto
Residential Detached zone (RD)
  1. 1 f30.0

    Frontage: at least 30.0 m.

  2. 2 a1850

    Lot area: at least 1850 m² per dwelling unit.

  3. 3 x975

    Site-specific exception 975: this site has rules of its own, written in the by-law.

  4. 4 Where this is written

    Chapter 10, section 10.20 of By-law 569-2013 · Exception 900.3.10(975)

  5. 5 What that means in practice

    These are the zone’s rules, not permission for this lot. What can be built also depends on the exceptions, overlays and setbacks that apply here. Confirm with the City before you plan.

City of Toronto Zoning By-law 569-2013, read at this address from the City’s zoning map. Open the City’s zoning map. Contains information licensed under the Open Government Licence – Toronto.

Permit history

2 building permits cleared at this address in the City’s file.

  • Interior AlterationsClosed

    Proposal for interior alterations to the ground floor of existing detached single family dwelling. Scope of work includes new window.

    Issued February 21, 2017

  • Building Permit Related(PS)Closed

    Plumbing - Proposal for interior alterations to the ground floor of existing detached single family dwelling. Scope of work includes new window.

    Issued February 21, 2017

City of Toronto Open Data — cleared building permits, which begin in 2017. Contains information licensed under the Open Government Licence – Toronto.

Signals around this home

Changing nearby

Changing nearby. 6 open development applications within 800 m of this home.

  • 2654 BAYVIEW AVEOfficial plan or zoning amendmentUnder Review

    OPA and Zoning By-law Amendment Application proposes the development of a 7-storey residential building. The building will provide a total of 168 residential units, being a mix of 1-bedroom, 2-bedroom and 3-bedrooms. A paved access from Bayview Ave along the southern property line will be provided, leading to 2 levels of below-grade parking, providing a total of 184 parking spaces; as well as 127 bicycle parking spaces. The proposed development provides a total GFA of 22,102.00 square metres and a FSI of 2.85. Additionally, the proposed development provides 336.00 square metres of indoor amenity space and 680.00 square metres of outdoor amenity space.


    320 m away

  • 2654 BAYVIEW AVEPlan of subdivisionUnder Review

    INACTIVE Plan of Subdivision application to permit twelve townhouses fronting onto Bayview Avenue and 5 single detached dwellings fronting onto a new public street (Ref: 18 140522 NNY 25 OZ).


    320 m away

  • 2660 BAYVIEW AVEOfficial plan or zoning amendmentUnder Review

    OPA and Zoning By-law Amendment Application proposes the development of a 7-storey residential building. The building will provide a total of 168 residential units, being a mix of 1-bedroom, 2-bedroom and 3-bedrooms. A paved access from Bayview Ave along the southern property line will be provided, leading to 2 levels of below-grade parking, providing a total of 184 parking spaces; as well as 127 bicycle parking spaces. The proposed development provides a total GFA of 22,102.00 square metres and a FSI of 2.85. Additionally, the proposed development provides 336.00 square metres of indoor amenity space and 680.00 square metres of outdoor amenity space.


    350 m away

  • 2660 BAYVIEW AVEPlan of subdivisionUnder Review

    INACTIVE Plan of Subdivision application to permit twelve townhouses fronting onto Bayview Avenue and 5 single detached dwellings fronting onto a new public street (Ref: 18 140522 NNY 25 OZ).


    350 m away

  • 2656 BAYVIEW AVEPlan of subdivisionUnder Review

    INACTIVE Plan of Subdivision application to permit twelve townhouses fronting onto Bayview Avenue and 5 single detached dwellings fronting onto a new public street (Ref: 18 140522 NNY 25 OZ).


    350 m away

  • 2656 BAYVIEW AVEOfficial plan or zoning amendmentUnder Review

    OPA and Zoning By-law Amendment Application proposes the development of a 7-storey residential building. The building will provide a total of 168 residential units, being a mix of 1-bedroom, 2-bedroom and 3-bedrooms. A paved access from Bayview Ave along the southern property line will be provided, leading to 2 levels of below-grade parking, providing a total of 184 parking spaces; as well as 127 bicycle parking spaces. The proposed development provides a total GFA of 22,102.00 square metres and a FSI of 2.85. Additionally, the proposed development provides 336.00 square metres of indoor amenity space and 680.00 square metres of outdoor amenity space.


    350 m away

City of Toronto Open Data — Development Applications and Building Permits (cleared permits since 2017). An application is a proposal: it may change, be refused or never be built. Contains information licensed under the Open Government Licence – Toronto.

The market

Detached homes for sale in St. Andrew-Windfields right now

For sale now
78
Median asking price
$4.34M

Middle half: $2.92M to $5M

New in 7 days
2

17 in 28 days

Price cuts
14%

11 listings

This home is asking 61% above the median, higher than three quarters of them.

See all homes in St. Andrew-Windfields

Asking 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

Transit nearby

StationLinesDistance
Bayview StationTTC subway: Line 4 Sheppard1.5 km
York Mills StationTTC subway: Line 1 Yonge-University1.7 km
Oriole GOGO Transit train: Richmond Hill2.4 km
Finch StationTTC subway: Line 1 Yonge-UniversityYRT bus rapid transit: Viva Blue3.7 km
Leaside StationTTC light rail: Line 5 Eglinton4.9 km

The nearest subway, light rail, train, bus rapid transit stations 5 km, as the crow flies. Source: TTC schedule data (GTFS) from the Toronto Transit Commission under the Open Government Licence – Toronto; GO Transit schedule data (GTFS) from Metrolinx under the Open Government Licence – Ontario – Metrolinx; YRT schedule data (GTFS) from York Region Transit under the YRT Open Data Licence 2.0, downloaded October 18, 2026. Contains information licensed under the Open Government Licence – Toronto. Data used in this product or service is provided with the permission of Metrolinx. Metrolinx makes no representations or warranties of any kind, express or implied, with respect to the Data and assumes no responsibility for the accuracy or currency of the data used in this product or service. Contains information licensed under the Open Government Licence – Ontario – Metrolinx. Contains public transit Information made available under YRT's Open Data Licence.

Schools nearby

ElementaryTypeDistanceEQAO average 2024–25
Owen Public SchoolToronto DSBPublic · grades JK–5 · French Immersion600 m59%Grade 3 average
Harrison Public SchoolToronto DSBPublic · grades JK–51 km82%Grade 3 average
St Gabriel Catholic SchoolToronto CDSBCatholic · grades JK–81.7 km69%Grade 6 average
École élémentaire Paul-DemersConseil scolaire ViamondeFrench-language public · grades JK–63.8 km95%Grade 6 average
SecondaryTypeDistanceGrade 9 math 2024–25
York Mills Collegiate InstituteToronto DSBPublic · grades 9–12 · French Immersion1.3 km81%Grade 9 math
École secondaire Étienne-BrûléConseil scolaire ViamondeFrench-language public · grades 9–121.5 km77%Grade 9 math
Cardinal Carter Academy for the ArtsToronto CDSBCatholic · grades 9–122 km87%Grade 9 math
Earl Haig Secondary SchoolToronto DSBPublic · grades 9–122.2 km84%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

Similar Active Listings

Recently sold nearby

Sold prices in St. Andrew-Windfields are shown to signed-in members.

Email Kassaundra Dobson, Broker of Record