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42 Glenayr Road

Forest Hill South / Toronto C03, ON M5P 3B8

ActiveFor Sale
5 Beds
4 Baths
2,000 Sq Ft
Single Family Home

About This Property

An extraordinary opportunity to create a landmark residence in one of Toronto's most prestigious neighbourhoods. Set on a prime, highly coveted west-facing lot, this offering sits on the iconic curved red cobblestone section of Glenayr Road - one of Forest Hill's most distinguished and sought-after streets, just moments from Forest Hill Village. The property boasts a rare and generous land parcel, beginning at 40 ft of frontage and widening to approximately 71 ft, with a depth of 172.6 ft and a total area of approximately 8,600+ sq ft, offering exceptional scale and presence. This unique offering comes with Committee of Adjustment approvals for a striking custom-designed three-storey estate by renowned architect Richard Wengle, envisioned at approximately 6,000+ sq ft above grade and over 10,000 sq ft of total living space. The proposed design showcases expansive principal rooms, an integral garage, and a resort-inspired outdoor setting complete with pool, cabana, and curated entertaining spaces. Full architectural plans have been thoughtfully prepared, presenting a rare opportunity to bring a sophisticated vision to life with much of the groundwork already in place. The existing residence has been extensively prepared, offering flexibility for those who wish to proceed with the approved new build or explore a tailored transformation of the current structure. For the discerning builder, investor, or end-user, this is a rare chance to secure a premier property and step into an advanced-stage luxury project in an exceptional location. Property and improvements being sold in as-is, where-is condition. The current home has been demo'd back to the brick and is not liveable.

Property Details

StatusActive
Property TypeSingle Family Home
Listing TypeFor Sale
Interior Size2,000 sq ft
Bedrooms5
Bathrooms4
Postal CodeM5P 3B8
Last UpdatedAug 8, 2026 · 5:56 p.m.

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Features & Amenities

  • View
  • Fireplace
  • Air Conditioning
  • Basement

TRREB MLS® Attribution

MLS® C13081206

Listed by CHESTNUT PARK REAL ESTATE LIMITED

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.

$4,500,000

asking price

MLS®C13081206
TypeSingle Family Home
CityToronto C03
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Team Filipe · RE/MAX · (647) 210-6070

Mortgage Estimate

Est. Monthly Payment

$21,974

/month · $3,600,000 mortgage

Down Payment20% — $900,000
Interest Rate5.5%

Amortization

Total Interest

$2,992,228

Total Cost

$6,592,228

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

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Listed By

CHESTNUT PARK REAL ESTATE LIMITED