21 Fifeshire Road

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

Overview

At a glance

Days on market40 days
ListedSep 17, 2026
UpdatedSep 17, 2026
Size5000 + sq ft
Lot121.89 x 178.36 Feet
Property taxes$23,377 (2025)
Parking14 spaces
BasementWalk-Up, Finished
MLS® numberC13797004
Data sourcePropTx MLS® System
Listing brokerageRE/MAX REALTRON BARRY COHEN HOMES INC.

About this home

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.

Details

Property

Style
2-Storey
Fronting on
North
Cross street
Bayview Ave and York Mills Rd
Community
St. Andrew-Windfields
Municipality
Toronto C12

Inside

Bedrooms above grade
5
Bedrooms below grade
1
Bathrooms
8
Kitchens
1
Basement
Walk-Up, Finished
Family room
Yes
Fireplace
Yes
Interior features
Auto Garage Door Remote, Central Vacuum, ERV/HRV, Sauna, Steam Room, Water Heater

Utilities

Heating
Forced Air
Heating fuel
Gas
Cooling
Central Air
Sewer
Sewer

Building

Construction
Stucco (Plaster)
Foundation
Concrete
Roof
Shingles
Pool
Inground

Parking

Garage
Built-In
Parking spaces
12
Total parking
14
Driveway
Circular Drive

Land

Frontage
121.89
Depth
178.36
Lot size units
Feet
Lot irregularities
East Depth 165.21'
Waterfront
No
Property features
Golf, Hospital, Library, Park, School
Rooms (13)
RoomLevelSizeFeatures
FoyerMain9.6 x 3.53Marble Floor, Double Closet, Crown Moulding
Living RoomMain9.6 x 3.94Hardwood Floor, Picture Window, Overlooks Frontyard
Bedroom 5Second4.27 x 3.3Double Closet, Hardwood Floor, Combined w/Sitting
KitchenMain4.47 x 4.04Breakfast Area, Centre Island, Marble Floor
Dining RoomMain4.5 x 3.94Bay Window, Crown Moulding, Overlooks Living
BedroomLower4.34 x 3.893 Pc Ensuite, Pot Lights, Closet
Family RoomMain7.52 x 4.47W/O To Terrace, Skylight, Fireplace
Bedroom 3Second4.9 x 3.94Closet, Overlooks Backyard, Hardwood Floor
Bedroom 2Second6.53 x 4.04Hardwood Floor, Double Closet, Overlooks Frontyard
RecreationLower11.35 x 3.81Wet Bar, Fireplace, Above Grade Window
Bedroom 4Second3.3 x 3.15Hardwood Floor, Overlooks Garden, Double Closet
Primary BedroomSecond12.7 x 5.285 Pc Ensuite, Walk-In Closet(s), Combined w/Sitting
OfficeMain6.5 x 5.33Fireplace, Overlooks Frontyard, Hardwood Floor
Value

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History

Listing history

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Neighbourhood

Around St. Andrew-Windfields

What’s nearby

On a busier streetBackyard faces north

  • Elementary schoolOwen Public Schoolabout 9 min walk
  • High schoolSt. Andrew's Junior High Schoolabout 4 min walk
  • ParkSt. Andrew’s Parkabout 2 min walk
  • Playground about 7 min walk
  • Trail about 2 min walk
  • River or lakeWilket Creekabout 6 min walk
  • Grocery storeMetroabout 11 min walk
  • DowntownTorontoabout 11.2 km
  • LibraryToronto Public Library - North York Central Libraryabout 2.6 km
  • Rec centre or arenaYork Mills Arenaabout 12 min walk
  • Golf courseRosedale Golf Clubabout 29 min walk
  • HospitalNorth York General Hospitalabout 2.7 km
  • Highway on-rampExit 371about 13 min walk
  • GO or train stationOrioleabout 34 min walk

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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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 RE/MAX REALTRON BARRY COHEN HOMES INC.. 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 27, 2026 at 10:51 p.m.

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