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21 Fifeshire Road
St. Andrew-Windfields Toronto M2L 2G4

$7,500,000
Residential Freehold beds: 5+1 baths: 8.0

Main Photo: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 1: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 2: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 3: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 4: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 5: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 6: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 7: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 8: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 9: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 10: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 11: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 12: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 13: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 14: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 15: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 16: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 17: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 18: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 19: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 20: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 21: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 22: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 23: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 24: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 25: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 26: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 27: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 28: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 29: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 30: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 31: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 32: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 33: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 34: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 35: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 36: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 37: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 38: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 39: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 40: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 41: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 42: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 43: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 44: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 45: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 46: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Photo 47: 21 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13250474
Status:
Active
Prop. Type:
Residential Freehold
MLS® Num:
C13250474
Bedrooms:
5+1
Bathrooms:
8
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.
Property Type:
Residential Freehold
Property Sub Type:
Detached
Home Style:
2-Storey
Total Approx Floor Area:
5000 +
Lot Depth:
178'4"
Lot Frontage:
121'11"
Direction Faces:
North
Bedrooms:
5+1
Bathrooms:
8.0
Water supply:
Municipal
Kitchens:
1
Bedrooms Above Grade:
5
Bedrooms Below Grade:
1
Kitchens Above Grade:
1
Rooms Above Grade:
12
Rooms Below Grade:
3
Heating type:
Forced Air
Heating Fuel:
Gas
Fireplaces:
4
Foundation:
Concrete
Roof:
Shingles
Basement:
Walk-Up, Finished
Fireplace/Stove:
Yes
Garage:
Built-In
Garage Spaces:
2.0
Parking Features:
Circular Drive
Parking Spaces:
12
Total Parking Spaces:
14.0
Family Room:
Yes
Possession Details:
TBD
Lot Irregularities:
East Depth 165.21'
Pool:
Inground
Link:
No
HST Applicable To Sale Price:
Included In
Taxes:
$23,377 / 2025
Assessment:
$- / -
Toronto
Toronto C12
St. Andrew-Windfields
Golf, Hospital, Library, Park, School
Auto Garage Door Remote, Central Vacuum, ERV/HRV, Sauna, Steam Room, Water Heater
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
Stucco (Plaster)
Floor
Type
Size
Other
Main
Foyer
9'6" × 7'5"
Marble Floor, Double Closet, Crown Moulding
Main
Living Room
10'10" × 9'6"
Hardwood Floor, Picture Window, Overlooks Frontyard
Main
Dining Room
10'10" × 4'5"
Bay Window, Crown Moulding, Overlooks Living
Main
Kitchen
7'11" × 4'4"
Breakfast Area, Centre Island, Marble Floor
Main
Office
7'9" × 6'5"
Fireplace, Overlooks Frontyard, Hardwood Floor
Main
Family Room
11'4" × 7'11"
W/O To Terrace, Skylight, Fireplace
Second
Primary Bedroom
12'7" × 7'4"
5 Pc Ensuite, Walk-In Closet(s), Combined w/Sitting
Second
Bedroom 2
10'5" × 4'4"
Hardwood Floor, Double Closet, Overlooks Frontyard
Second
Bedroom 3
10'10" × 4'9"
Closet, Overlooks Backyard, Hardwood Floor
Second
Bedroom 4
4'3" × 3'3"
Hardwood Floor, Overlooks Garden, Double Closet
Second
Bedroom 5
6'3" × 3'3"
Double Closet, Hardwood Floor, Combined w/Sitting
Lower
Bedroom
10'5" × 6'10"
3 Pc Ensuite, Pot Lights, Closet
Lower
Recreation
13'11" × 9'9"
Wet Bar, Fireplace, Above Grade Window
Special Designation:
Unknown
Sewers:
Sewer
Air Conditioning:
Central Air
Central Vacuum:
Yes
Seller Property Info Statement:
No
Laundry Level:
Main Level
Date Listed:
Jun 05, 2026
Original Price:
Previous Price:
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Listed by RE/MAX REALTRON BARRY COHEN HOMES INC.
Data was last updated June 24, 2026 at 02:15 AM (UTC)
Area Statistics
Listings on market:
87
Avg list price:
$4,850,000
Min list price:
$1,849,900
Max list price:
$18,000,000
Avg days on market:
34
Min days on market:
1
Max days on market:
416
These statistics are generated based on the current listing's property type and located in St. Andrew-Windfields. Average values are derived using median calculations. This data is not produced by the MLS® system.
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.