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38 Fifeshire Road

St. Andrew-Windfields / Toronto C12, ON M2L 2G6

ActiveFor Sale
5 Beds
5 Baths
3,000 Sq Ft
20,505 Lot Sq Ft
Single Family Home
Virtual Tour Available

About This Property

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

StatusActive
Property TypeSingle Family Home
Listing TypeFor Sale
Interior Size3,000 sq ft
Lot Size20,505 sq ft
Bedrooms5
Bathrooms5
Postal CodeM2L 2G6
Last UpdatedAug 8, 2026 · 6:52 p.m.

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Features & Amenities

  • View
  • Fireplace
  • Air Conditioning
  • Basement

TRREB MLS® Attribution

MLS® C13109790

Listed by HARVEY KALLES REAL ESTATE LTD.

The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by The Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA. The trademarks REALTOR®, REALTORS® and the REALTOR® logo are controlled by CREA and identify real estate professionals who are members of CREA. Listing data provided by the Toronto Regional Real Estate Board (TRREB). The information contained herein is from sources believed to be reliable but is not guaranteed. Information deemed reliable but not guaranteed accurate by TRREB or Team Filipe / RE/MAX.

$4,995,000

asking price

MLS®C13109790
TypeSingle Family Home
CityToronto C12
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Team Filipe · RE/MAX · (647) 210-6070

Mortgage Estimate

Est. Monthly Payment

$24,391

/month · $3,996,000 mortgage

Down Payment20% — $999,000
Interest Rate5.5%

Amortization

Total Interest

$3,321,373

Total Cost

$7,317,373

Estimate only. Based on Canadian semi-annual compounding, 25-yr amortization at 5.5%.

Full Mortgage Calculator →

Listed By

HARVEY KALLES REAL ESTATE LTD.