38 Fifeshire Road, Toronto, ON
St. Andrew-Windfields, Toronto · MLS® C13109790
About this home
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.
Key facts
- Property type
- Detached, 2-Storey
- MLS®
- C13109790
- Bedrooms
- 5 (4 + 1)
- Bathrooms
- 5 (2 half)
- Size
- 3000-3500
- 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
- 71
- Listing brokerage
- HARVEY KALLES REAL ESTATE LTD.
Rooms
overlooks garden · b/i shelves · broadloom
large closet · broadloom · picture window
beamed ceilings · fireplace · overlooks backyard
large window · large closet · broadloom
overlooks backyard · large window
2 pc ensuite · walk-in closet(s) · picture window
b/i appliances · breakfast area · tile floor
6 pc ensuite · walk-in closet(s) · double closet
overlooks backyard · window floor to ceiling · broadloom
w/o to yard · stone fireplace
double closet · broadloom · picture window
Heads up: the asking price here sits well above what comparable listings suggest. That can point to premium finishes, a bigger lot, or simply an ambitious ask, so it is worth a close look before you offer. I would not put an automatic figure on this one. Tell me you are interested and I will pull the most comparable recent sales and give you a straight answer on what it will really take.
Ask Moe if this price is fairOn 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.
On location, this is a more car-dependent spot, so buyers here typically drive. Toba Dr at Fifeshire Rd is about a 3-minute walk away. Worth weighing if transit access matters to you.
What the listing highlightsThese are claims from the listing. The only way to know for sure is to see it in person, and I am happy to book you a private showing.
- Ravine lot: privacy and premium value, but confirm the buildable area and any conservation limits.
- Premium lot / gardens: lot size and privacy hold value and cannot be changed, verify frontage, depth, and any easements.
- Development potential: upside only if zoning permits, verify with the city before relying on it.
- Worth verifying
- Value driver
The closest active listings by size, beds, and price, so you can see what this home is up against.
The 4 closest active listings nearby.
See all comparable homes70 days longer than the Toronto average (1 days).
View comparable listingsPrice per square foot vs the area average.
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.
Getting around
Car-DependentA walkability read built from the amenities around this home: how close the nearest transit stop is, and how many grocery, dining, park, and pharmacy destinations fall within a 15-minute walk. It is a guide, not a guarantee. Places data from Google.
Almost all errands require a car — groceries and transit are a drive away.
🚉 Nearest transit: Toba Dr at Fifeshire Rd, about 236 m away
Within a 15-minute (1.5 km) walk.
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.
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 3.99% via Ratehub.ca (as of July 22, 2026); conventional rates run a little higher.
Mortgage amount $3,996,000 · 4.14% over 25 years
Total monthly cost
- Mortgage payment (monthly equivalent)
- $21,324
- Property tax
- $1,258
- Condo / maintenance fees
- $0
- Heating
- $0
- Estimated monthly cost
- $22,582
Add your own property tax, condo fees, and heating on the left for a sharper total.
One-time closing costs
- Ontario land transfer tax
- $111,350
- Toronto municipal land transfer tax
- $141,250
- Estimated closing costs
- $252,600
Plus your down payment of $999,000. 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
- $1,279,448
- Principal paid down
- $508,892
- Interest paid
- $770,557
- Balance remaining
- $3,487,108
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
Income potential: the basement has a separate entrance, which often supports a rentable in-law or second suite. That can lift real rent well above the figure above and help carry the mortgage. Ask us about permitted use in this area.
Thinking of this home as an investment? We will pull real comparable rents and run the full numbers with you.
Talk about the numbersEstimates only. Rent is modelled on above-grade size and local norms, so a finished basement or second suite (a separate entrance often means one) can push real rent well above this. Taxes, fees, and vacancy vary by property, and cap rate is before financing. A starting point, not a final number, let us run the real ones with you.
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.