
































42 Glenayr Road
Forest Hill South, Toronto
$4,500,000
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.
No extras listed.
Visit this home
Pick a time that works for you.
No upcoming open houses.
Ask my AI assistant
Schools, payments, offer timing, history — ask in plain words. This home is already in the conversation.
| Type | Detached |
| Style | 2-Storey |
| Approx. Age | Not available |
| Size | 2000-2500 sq. ft. |
| Property Tax | $18,316 |
| Lot Size | 40 ft x 159.41 ft |
| mls© Number | C13081206 |
| Listed By | CHESTNUT PARK REAL ESTATE LIMITED |
Listing History
- No recent sale history for this listing.
- No recent lease history for this listing.
Schools
Could you afford this home?
What the bank counts
This home's actual carrying costs, payment stress-tested at 6%
- Mortgage, tested at 6%
- $23,033
- Property tax
- $1,526
- Heat allowance
- $150
- Housing costs
- $24,709 / mo
Lenders cap these at 39% of gross income — that sets the number.
Income needed
$760,000
gross annual household income
- Payment at 4%
- $18,937 / mo
- Cash down
- $900,000
Assumes no other monthly debts · 25-yr amortization
Full affordability checkInvestment Analysis
Estimated rent, cap rate and monthly cash flow for this property
Values and trends
Nearby listings
Comparable sales
- No similar listings found.














































































































































































































































































































































































































































































































































































































































































































































































































