38 Fifeshire Road • Toronto, ON photo 1
38 Fifeshire Road • Toronto, ON photo 2
38 Fifeshire Road • Toronto, ON photo 3
38 Fifeshire Road • Toronto, ON photo 4
38 Fifeshire Road • Toronto, ON photo 5
38 Fifeshire Road • Toronto, ON photo 6
38 Fifeshire Road • Toronto, ON photo 7
38 Fifeshire Road • Toronto, ON photo 8
38 Fifeshire Road • Toronto, ON photo 9
38 Fifeshire Road • Toronto, ON photo 10
38 Fifeshire Road • Toronto, ON photo 11
38 Fifeshire Road • Toronto, ON photo 12
38 Fifeshire Road • Toronto, ON photo 13
38 Fifeshire Road • Toronto, ON photo 14
38 Fifeshire Road • Toronto, ON photo 15
38 Fifeshire Road • Toronto, ON photo 16
38 Fifeshire Road • Toronto, ON photo 17
38 Fifeshire Road • Toronto, ON photo 18
38 Fifeshire Road • Toronto, ON photo 19
38 Fifeshire Road • Toronto, ON photo 20
38 Fifeshire Road • Toronto, ON photo 21
38 Fifeshire Road • Toronto, ON photo 22
38 Fifeshire Road • Toronto, ON photo 23
38 Fifeshire Road • Toronto, ON photo 24
38 Fifeshire Road • Toronto, ON photo 25
38 Fifeshire Road • Toronto, ON photo 26
38 Fifeshire Road • Toronto, ON photo 27
38 Fifeshire Road • Toronto, ON photo 28
38 Fifeshire Road • Toronto, ON photo 29
38 Fifeshire Road • Toronto, ON photo 30
38 Fifeshire Road • Toronto, ON photo 31
38 Fifeshire Road • Toronto, ON photo 32
38 Fifeshire Road • Toronto, ON photo 33
38 Fifeshire Road • Toronto, ON photo 34
38 Fifeshire Road • Toronto, ON photo 35
38 Fifeshire Road • Toronto, ON photo 36
38 Fifeshire Road • Toronto, ON photo 37
38 Fifeshire Road • Toronto, ON photo 38
38 Fifeshire Road • Toronto, ON photo 39
38 Fifeshire Road • Toronto, ON photo 40
1 / 40
$4,995,000
38 Fifeshire Road • Toronto, ONNew
Courtesy of HARVEY KALLES REAL ESTATE LTD.
4+1
Bedrooms
5
Bathrooms
3000-3500
Square feet
12
Parking

About this home

A rare legacy estate awaits! Seize the opportunity to build your dream home on one of Toronto's most prestigious streets. Nestled in the heart of the coveted Bayview and York Mills enclave, 38 Fifeshire Road presents an exceptional offering to create a bespoke masterpiece in one of the city's most distinguished neighbourhoods. Spanning nearly 1/2 an acre, this expansive ravine lot is a canvas of serenity and prestige, framed by lush greenery, mature trees, and the tranquil beauty of its natural surroundings. With exceptional frontage, depth, and breathtaking ravine vistas, this property is a dream for visionary architects and discerning homeowners. The existing residence, boasting nearly 5,000 square feet of well-appointed living space, provides a foundation of grandeur, yet the true allure lies in the lands potential. Imagine a custom-designed estate with sweeping outdoor terraces, infinity pools, or private gardens all tailored to your unique vision of luxury. Located just moments from Toronto's finest offerings, including Bayview Villages upscale shopping, elite private and public schools, gourmet dining, exclusive clubs, and seamless access to Highway 401 & DVP, this address marries tranquility with connectivity. 38 Fifeshire Road is not merely a home its a legacy in the making, a rare chance to define timeless elegance on one of Toronto's most iconic streets.

Property details

Property type
Detached
Style
2-Storey
Total rooms
9
Lot size
117.88 × 199.45 ft
Property taxes
$15,099.75 (2025)
Occupancy
30-60 TBA
Days on market
111
Status
Active
MLS®

Property history

Recently sold nearby

Listing data last updated: Aug 28, 2026, 3:27 p.m. EDT via TRREB IDX.

First listed: May 11, 2026, 9:27 a.m. EDT.