Forgot password Extend Verify Contact

38 Fifeshire Road
St. Andrew-Windfields Toronto M2L 2G6

$4,549,999
Residential Freehold beds: 4+1 baths: 5.0

Main Photo: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 1: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 2: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 3: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 4: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 5: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 6: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 7: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 8: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 9: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 10: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 11: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 12: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 13: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 14: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 15: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 16: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 17: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 18: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 19: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 20: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 21: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 22: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 23: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 24: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 25: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 26: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 27: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 28: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 29: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 30: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 31: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 32: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 33: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 34: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 35: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 36: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 37: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 38: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 39: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Photo 40: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
Status:
Active
Prop. Type:
Residential Freehold
MLS® Num:
C13784786
Bedrooms:
4+1
Bathrooms:
5
A rare ravine lot, nearly half an acre in size! Seize the opportunity to build your dream home on one of Toronto's most prestigious streets, in the coveted Bayview and York Mills enclave. 38 Fifeshire Road offers a canvas of serenity and prestige - framed by mature trees and lush natural surroundings - ideal for visionary architects and discerning homeowners. The existing residence offers nearly 5,000 square feet of living space, but the true allure lies in the land's potential: imagine a custom estate with sweeping terraces, an infinity pool, or private gardens, tailored to your vision. Just moments from Bayview Village, top schools, fine dining, and easy access to major highways. This is more than a home - it's a legacy in the making on one of Toronto's most iconic streets.
Property Type:
Residential Freehold
Property Sub Type:
Detached
Home Style:
2-Storey
Total Approx Floor Area:
3000-3500
Lot Depth:
199'5"
Lot Frontage:
117'10½"
Lot Shape:
Irregular
Direction Faces:
West
Bedrooms:
4+1
Bathrooms:
5.0
Water supply:
Municipal
Kitchens:
1
Bedrooms Above Grade:
4
Bedrooms Below Grade:
1
Kitchens Above Grade:
1
Rooms Above Grade:
9
Rooms Below Grade:
3
Heating type:
Forced Air
Heating Fuel:
Gas
Foundation:
Concrete
Roof:
Asphalt Shingle
Basement:
Finished with Walk-Out
Fireplace/Stove:
Yes
Garage:
Built-In
Garage Spaces:
2.0
Parking Features:
Circular Drive
Parking Spaces:
10
Total Parking Spaces:
12.0
Family Room:
Yes
Possession Details:
30/60 TBA
Lot Irregularities:
106.23 ft rear & 164.02 ft on other side
Pool:
Inground
Link:
No
HST Applicable To Sale Price:
Included In
Taxes:
$15,099.75 / 2025
Assessment:
$- / -
Toronto
Toronto C12
St. Andrew-Windfields
None
Hot water tank if a rental
All existing appliances & window coverings. All existing light fixtures except chandeliers listed In exclusions.
Dining room & all bedrooms chandeliers, Main floor foyer & 2nd floor foyer chandeliers.
Brick
Floor
Type
Size
Other
Main
Living Room
22'1" × 14'10¾"
Overlooks Backyard, Window Floor to Ceiling, Broadloom
Main
Dining Room
14'10" × 13'1"
Overlooks Backyard, Large Window
Main
Kitchen
17'5" × 13'3"
B/I Appliances, Breakfast Area, Tile Floor
Main
Family Room
18'3" × 12'8"
Beamed Ceilings, Fireplace, Overlooks Backyard
Main
Office
11' × 9'11"
Overlooks Garden, B/I Shelves, Broadloom
Second
Primary Bedroom
19'1½" × 14'10¾"
6 Pc Ensuite, Walk-In Closet(s), Double Closet
Second
Bedroom 2
14'11½" × 12'4"
Large Closet, Broadloom, Picture Window
Second
Bedroom 3
14'½" × 11'10½"
Double Closet, Broadloom, Picture Window
Second
Bedroom 4
13' × 11'5"
2 Pc Ensuite, Walk-In Closet(s), Picture Window
Lower
Recreation
24'9¼" × 14'5¼"
W/O To Yard, Stone Fireplace
Lower
Bedroom
11'9¾" × 9'10"
Large Window, Large Closet, Broadloom
Special Designation:
Unknown
Sewers:
Sewer
Air Conditioning:
Central Air
Central Vacuum:
No
Seller Property Info Statement:
No
Date Listed:
Sep 15, 2026
Original Price:
Previous Price:
  • Photo 1: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 1 of 40
  • Photo 2: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 2 of 40
  • Photo 3: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 3 of 40
  • Photo 4: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 4 of 40
  • Photo 5: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 5 of 40
  • Photo 6: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 6 of 40
  • Photo 7: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 7 of 40
  • Photo 8: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 8 of 40
  • Photo 9: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 9 of 40
  • Photo 10: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 10 of 40
  • Photo 11: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 11 of 40
  • Photo 12: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 12 of 40
  • Photo 13: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 13 of 40
  • Photo 14: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 14 of 40
  • Photo 15: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 15 of 40
  • Photo 16: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 16 of 40
  • Photo 17: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 17 of 40
  • Photo 18: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 18 of 40
  • Photo 19: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 19 of 40
  • Photo 20: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 20 of 40
  • Photo 21: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 21 of 40
  • Photo 22: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 22 of 40
  • Photo 23: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 23 of 40
  • Photo 24: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 24 of 40
  • Photo 25: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 25 of 40
  • Photo 26: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 26 of 40
  • Photo 27: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 27 of 40
  • Photo 28: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 28 of 40
  • Photo 29: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 29 of 40
  • Photo 30: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 30 of 40
  • Photo 31: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 31 of 40
  • Photo 32: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 32 of 40
  • Photo 33: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 33 of 40
  • Photo 34: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 34 of 40
  • Photo 35: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 35 of 40
  • Photo 36: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 36 of 40
  • Photo 37: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 37 of 40
  • Photo 38: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 38 of 40
  • Photo 39: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 39 of 40
  • Photo 40: 38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C13784786
    Photo 40 of 40
Listed by HARVEY KALLES REAL ESTATE LTD.
Data was last updated September 19, 2026 at 04:15 AM (UTC)
Area Statistics
Listings on market:
71
Avg list price:
$4,790,000
Min list price:
$1,248,000
Max list price:
$30,000,000
Avg days on market:
53
Min days on market:
2
Max days on market:
227
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.
JIM STANTON
BEN STANTON
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.