38 Fifeshire Road, Toronto, ON
St. Andrew-Windfields, Toronto · MLS® C13784786
About this home
In short
- A rare ravine lot, nearly half an acre in size.
- Seize the opportunity to build your dream home on one of Toronto's most prestigious streets, in the coveted Bayview and York Mills enclave.
- 38 Fifeshire Road offers a canvas of serenity and prestige - framed by mature trees and lush natural surroundings - ideal for visionary architects and discerning...
- The existing residence offers nearly 5,000 square feet of living space, but the true allure lies in the land's potential: imagine a custom estate with sweeping...
A rare ravine lot, nearly half an acre in size! Seize the opportunity to build your dream home on one of Toronto's most prestigious streets, in the coveted Bayview and York Mills enclave. 38 Fifeshire Road offers a canvas of serenity and prestige - framed by mature trees and lush natural surroundings - ideal for visionary architects and discerning homeowners. The existing residence offers nearly 5,000 square feet of living space, but the true allure lies in the land's potential: imagine a custom estate with sweeping terraces, an infinity pool, or private gardens, tailored to your vision. Just moments from Bayview Village, top schools, fine dining, and easy access to major highways. This is more than a home - it's a legacy in the making on one of Toronto's most iconic streets.
Key facts
- Property type
- Detached, 2-Storey
- MLS®
- C13784786
- Bedrooms
- 4+1 (5 total)
- Bathrooms
- 5 (2 half)
- Size
- 3000-3500 sq ft
- Lot
- 117.88 × 199.45 ft
- Cross streets
- Bayview/York Mills
- Parking
- 2 garage · 12 parking (built-in)
- Driveway
- Circular Drive
- Basement
- Finished with Walk-Out
- Heating
- Forced Air
- A/C
- Central Air
- Exterior
- Brick
- Foundation
- Concrete
- Roof
- Asphalt Shingle
- Sewer
- Sewer
- Pool
- Inground
- Property tax
- $15,100 / 2025
- Days on market
- 22
- Listing brokerage
- HARVEY KALLES REAL ESTATE LTD.
Rooms
overlooks backyard · large window
overlooks garden · b/i shelves · broadloom
b/i appliances · breakfast area · tile floor
2 pc ensuite · walk-in closet(s) · picture window
large window · large closet · broadloom
large closet · broadloom · picture window
double closet · broadloom · picture window
6 pc ensuite · walk-in closet(s) · double closet
overlooks backyard · window floor to ceiling · broadloom
w/o to yard · stone fireplace
beamed ceilings · fireplace · overlooks backyard
Listed at $4,549,999. Going by how homes in St. Andrew-Windfields and the wider GTA have actually closed against their asking prices (about 96%, 25 local closings in 90 days), the likely sale price is near $4.38M, if it sells. A realistic range is $4.11M to $4.94M.
Independent value check: no figure for this home. Going only by the sales record, our model lands more than 25% below the ask. At that distance an automated figure has rarely been close to the eventual sale price, so we are not printing one. The usual reason is something the record cannot show: a rebuild, a second unit, or a lot or setting unlike the homes around it.
Total price vs nearby homes. Likely closing about $4.38M, from 25 recent closings in this pocket.
The market behind the math:
About 1.9 months of inventory: 16 detached homes for sale in the area against 25 closings in the last 90 days. Under two months favours sellers, over four favours buyers.
Price per square foot: this home lists at $1,400/sqft against an area asking average of $932/sqft.
- Walk-out basement apartment features. A finished 1 bed walk-out basement apartment. A self-contained space for extended family, guests or potential income. In St. Andrew-Windfields basements rarely rent out (5 of 134 recent detached leases were basement units), so buyers here treat a suite as family or nanny space rather than income. Value it for the living space, not the rent. Second-suite retrofit status is not verified. A buyer intending to rent should confirm requirements with the City of Toronto.
- Ravine / green setting. This home is described as backing onto a ravine or green setting. The ravine backing is priced into the comparison. How much it is really worth depends on whether the house sits on table land with the slope well behind it, or drops away right behind it, and that part is my in-person call.
- Inground pool. Priced into the comparison on the assumption it is clean and modern. A pool costs more to build than resale pays back, and condition is the in-person call.
How this estimate is builtthe short version
This figure comes from a model built on about 44,000 recent GTA sales. It weighs this home’s tax assessment, size, age, location and features against what homes like it actually sold for, including sales in this neighbourhood.
It never sees the asking price. The 25 most comparable recent sales on their own, adjusted for size, beds, baths and lot, point to about $2.39M. Condition and finishes remain an in-person call.
What the listing highlights4 points to weigh
Claims from the listing, worth confirming in person. I can book you a private showing.
- Ravine lot: privacy and premium value, but confirm the buildable area and any conservation limits. Worth verifying
- Pool: lifestyle appeal, but adds maintenance, insurance, and resale is mixed. Weigh carefully
- Premium lot / gardens: lot size and privacy hold value and cannot be changed, verify frontage, depth, and any easements. Value driver
- Development potential: upside only if zoning permits, verify with the city before relying on it. Worth verifying
Schools & getting aroundcatchment and transit
On schools, this address is zoned for York Mills Collegiate Institute, one of the higher-rated public schools in the area. A strong catchment tends to hold value and widen your resale pool, especially with family buyers.
Based on 25 comparable homes that sold in St. Andrew-Windfields over the past two years, from 164 closings there.
For sale
For sale
For sale
For sale
For sale
For sale
For saleNothing closely matching this home is listed nearby right now, so these are the nearest detached listings on the market. Homes like this one have recently closed around $2.76M, which is where my estimate comes from.
Per square foot, these ask about $889/sqft; this home lists at $1,400/sqft. Size is part of the price story, not just the sticker.
The 5 closest of 7 active listings nearby.
See all comparable homesSold price trend
Median sold price for detached homes in St. Andrew-Windfields: $3.41M in September 2026, down 5% from a year ago, on 79 closings in 10 months.
Line: median sold price, each month averaged with its neighbours and weighted by closings. Bars: closings that month.
Month by month
| Month | Median sold | Closings |
|---|---|---|
| October 2025 | $3.71M | 7 |
| November 2025 | $2.59M | 6 |
| December 2025 | $2.08M | 8 |
| February 2026 | $2.95M | 7 |
| March 2026 | $2.27M | 8 |
| April 2026 | $2.92M | 8 |
| May 2026 | $2.29M | 10 |
| July 2026 | $2.62M | 12 |
| August 2026 | $2.35M | 7 |
| September 2026 | $3.41M | 6 |
Neighbourhood & location
St. Andrew-Windfields, Toronto, ON
Enter a workplace or destination and we’ll show the door-to-door time by car, transit and bike.
How asking prices compare in the closest areas to this home. Longer bars mean a pricier market.
Typical asking price of active listings of the same type, per area (outliers removed). Toronto.
Get the full neighbourhood report (schools, parks, transit & safety) →
The public and Catholic schools this address is zoned for, with EQAO results (the share of students meeting Ontario's provincial standard).
School attendance boundaries and EQAO results are Ontario government data and can change. Confirm the current catchment with the school board before relying on it.
Also nearby: 12 more schools within 2.5 km
Not the assigned catchment: schools a family here could reach, with EQAO results where published.
Affordability & Mortgage
Income needed assumes a ~32% GDS ratio; weekly is mortgage principal & interest only. Price ÷ income is the home price over the income needed. Fixed reference assumptions so listings compare on equal footing, not a lending decision.
Calculate and customize your mortgage and other expenses
Adjust the down payment, rate, and amortization, and add property tax, condo fees, and heating to see your true monthly cost.
Your numbers
Homes over $1.5M can't be insured, so 20% down or more is required.
Conventional (20%+ down). Best insured 5-year fixed 4.34% via Ratehub.ca (as of October 7, 2026); conventional rates run a little higher.
Mortgage amount $3,639,999 · 4.49% over 25 years
Total monthly cost
- Mortgage payment (monthly equivalent)
- $20,126
- Property tax
- $1,258
- Condo / maintenance fees
- $0
- Heating
- $0
- Estimated monthly cost
- $21,385
Add your own property tax, condo fees, and heating on the left for a sharper total.
One-time closing costs
- Ontario land transfer tax
- $100,225
- Toronto municipal land transfer tax
- $121,225
- Estimated closing costs
- $221,450
Plus your down payment of $910,000. Legal fees, title insurance, and adjustments are extra and vary by deal.
Mortgage stress test
Lenders qualify you at the greater of your rate plus 2% or 5.25%. You do not pay this rate. It just shows you could still handle payments if rates rose, so aim to stay comfortable at this higher number.
Over the full 25 years
At the end of your 5-year term
- Total paid over the term
- $1,207,571
- Principal paid down
- $444,741
- Interest paid
- $762,830
- Balance remaining
- $3,195,258
Talk to Team Asgarian about your options
Rates and programs change often. We will connect you with a trusted mortgage professional and build a plan that fits your budget and goals.
Estimates only, not a mortgage quote or pre-approval. Figures use Canadian semi-annual compounding, current minimum down-payment rules, CMHC premium tiers, and Ontario (plus Toronto, when selected) land transfer tax. Actual rates, taxes, insurance, and closing costs vary by lender and property. Confirm every number with your mortgage professional.
Investor snapshot
About the suite: in St. Andrew-Windfields basements rarely rent out (5 of 134 recent detached leases were basement units), so the figure above does not count it as income. Buyers here use a suite as family or nanny space.
Thinking of this home as an investment? We will pull real comparable rents and run the full numbers with you.
Talk about the numbersThe last 52 whole-home leases in St. Andrew-Windfields signed at a median of $5,380 a month; adjusted to this home for size, beds and baths, and for where rents stood the month each signed, that is $5,621. The gross yield above is on the asking price, before taxes and upkeep; the cap rate is after them. A finished basement or second suite can push real rent above it. Taxes, fees, and vacancy vary by property, and cap rate is before financing.
Helpful resources
All information deemed reliable but not guaranteed. For personal, non-commercial use only. Listing courtesy of HARVEY KALLES REAL ESTATE LTD.. MLS®/PropTx.