For Sale · Toronto (St. Andrew-Windfields) · Single Family

$4,995,000

38 FIFESHIRE ROAD, Toronto (St. Andrew-Windfields)

Beds

5 (2 half)

Baths

About This Home

The details.

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. (id:66635)

Summarizing the highlights...

MLS® C13109790Listing courtesy of HARVEY KALLES REAL ESTATE LTD.View on map Street view

Property Details

Facts & features.

Property type: Single Family
Ownership: Freehold
Storeys: 2
Parking: 12 spaces
Listed on: 2026-05-11
Days on market: 65
MLS number: C13109790
Data source: Toronto Regional Real Estate Board

July Value

What this home is worth.

Calculating a July Value estimate...

Realtor Recommended

JULY advisors for this home.

Bart Pukacz
Real Estate Advisor
Residential, Investment Properties, Presale Condos
Profile 604.721.1439
Han Lee
Real Estate Advisor
Residential, Investment Properties, Luxury Properties
Profile
Iñaki Sarmiento
Real Estate Advisor
Residential, Investment Properties
Profile 778.954.6254

My Notes

Track this home.

Write a note about this home

Location

Where it sits.

Open in full map search

Run The Numbers

Mortgage and cash flow.

Mortgage calculator.

Home priceDown payment20%Rate (%)Amortization

Monthly mortgage payment

$23,360

$3,996,000 financed over 25 years at 5%. For guidance only, not a quote or approval.

Cash flow analysis.

Property tax / moMaintenance / moRental income / mo

Monthly cost (mortgage + tax + maintenance)

$23,360

Cash flow

-$23,360

Estimates for education only. Talk to a JULY advisor for real numbers on this home.

Toronto (St. Andrew-Windfields) right now

Active listings

New this week

$4,099,900

Median asking price

Live snapshot from the MLS® feed. Sold-price history and trend charts arrive with our VOW data feed.

The Neighbourhood

Living in Toronto (St. Andrew-Windfields).

Household and demographic stats for Toronto (St. Andrew-Windfields), from the Statistics Canada 2021 Census.

2,794,356
Population (2021): 39.6
Median age: 1,160,895
Households: 2.4
Avg household size: 51.9%
Home ownership: $84,000
Median household income

Toronto (St. Andrew-Windfields) market trends

Source: Statistics Canada 2021 Census, Toronto, City, Ontario.

Schools

Nearby schools.

K-12 schools closest to this home, with straight-line distances.

St Andrew's Middle School
public · elementary
350 m
Owen Public School
public · elementary
610 m
Avondale Alternative Elementary School
public · elementary
880 m
Avondale Public School
public · elementary
880 m
Harrison Public School
public · elementary
1.2 km
Cornell International Academy
independent · secondary
1.2 km

Source: Statistics Canada, Open Database of Educational Facilities. Distances are straight-line, not walking routes. Catchment boundaries change; always confirm with the school district.

Similar Homes

Nearby homes like this one.

Rental Market

Renting nearby.

Active rentals close to this home, for rent-versus-buy context and investors sizing up cash flow.

Ask About This Home

Talk to a JULY advisor.

Interested in this home?

Book a viewing with a JULY advisor.

Listing information is provided courtesy of the Canadian Real Estate Association's Data Distribution Facility (DDF®) and is deemed reliable but is not guaranteed accurate by JULY Realty or CREA. The trademarks MLS®, Multiple Listing Service® and the associated logos identify professional services rendered by REALTOR® members of CREA to effect the purchase, sale and lease of real estate as part of a cooperative selling system. The trademarks REALTOR®, REALTORS® and the REALTOR® logo are controlled by CREA and identify real estate professionals who are members of CREA.