34 Medalist Road, Toronto, ON
St. Andrew-Windfields, Toronto · MLS® C13207292
About this home
Exceptional Custom-Built Residence In Prestigious St. Andrew-Windfields, Backing Onto A Beautiful Ravine-Like Setting And St. Andrews Park, Offering Rare Privacy And Serene Views. Thoughtfully Designed With An Owner-Built Level Of Care, Outstanding Craftsmanship, And Premium Finishes Throughout, This Architectural Masterpiece Blends Timeless Elegance With State-Of-The-Art Living. The Main Floor Features Heated Floors, Grand Principal Rooms, Expansive Imported Windows, Designer Lighting, Custom Millwork, And A Seamless Open-Concept Layout. The Chef's Dream Kitchen Is Equipped With High-End Appliances, Custom Cabinetry, And Natural Stone Countertops, Perfect For Both Everyday Living And Entertaining. A Private Elevator Services All Levels. The Second Floor Offers Four Spacious Bedrooms, Each With Its Own Ensuite Bathroom, Including A Luxurious Primary Retreat With A Spa-Inspired Ensuite And Custom Dressing Room. The Lower Level Includes A Home Theatre, Private Gym, Recreation Room, Wine Cellar, Prep Kitchen, Nanny Suite, And Walk-Out Access To The Backyard. Additional Highlights Include A Heated Driveway, Heated Main Floor, Home Automation, And A Six-Car Underground Garage With EV Charging. A Truly Rare Offering In One Of Toronto's Most Coveted Neighbourhoods.
Key facts
- Property type
- Detached, 2 1/2 Storey
- MLS®
- C13207292
- Bedrooms
- 5 (4 + 1)
- Bathrooms
- 8 (3 half)
- Size
- 5,000 sq ft
- Lot
- 72.29 × 129.83 ft
- Cross streets
- Bayview and Yorkmills
- Parking
- 5 garage · 10 parking (built-in)
- Driveway
- Private
- Basement
- Finished with Walk-Out
- Kitchens
- 2 (1 + 1)
- Heating
- Forced Air
- A/C
- Central Air
- Exterior
- Stone
- Foundation
- Unknown
- Roof
- Asphalt Shingle
- Sewer
- Sewer
- Pool
- Inground, Salt
- Property tax
- $37,048 / 2025
- Days on market
- 50
- Listing brokerage
- HARVEY KALLES REAL ESTATE LTD.
Rooms
fireplace · heated floor · coffered ceiling(s)
heated floor · pot lights · coffered ceiling(s)
centre island · breakfast area · b/i appliances
fireplace · walk-out · heated floor
b/i bookcase · window floor to ceiling · heated floor
ensuite bath · walk-in closet(s) · fireplace
walk-in closet(s) · ensuite bath · picture window
walk-in closet(s) · ensuite bath · picture window
walk-in closet(s) · ensuite bath · picture window
hardwood floor · picture window · b/i shelves
laundry sink · picture window · b/i closet
picture window · b/i bookcase · b/i desk
fireplace · walk-out · heated floor
built-in speakers · broadloom · panelled
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, it is moderately walkable, so some daily errands are within reach and for the rest you will likely drive. Toba Dr at Fifeshire Rd is about a 5-minute walk away.
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.
- Upscale kitchen: a genuine value driver, verify the appliances, stone, and finishes in person.
- Heated floors: comfort and a premium-finish signal.
- Primary suite: a key comfort and resale feature.
- Open-concept layout: modern, sought-after flow.
- Worth verifying
- Value driver
- Lifestyle
The closest active listings by size, beds, and price, so you can see what this home is up against.
The 5 closest of 8 active listings nearby.
See all comparable homes49 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
WalkableA 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.
Many errands can be done on foot; a car still helps.
🚉 Nearest transit: Toba Dr at Fifeshire Rd, about 432 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 17, 2026); conventional rates run a little higher.
Mortgage amount $8,796,000 · 4.14% over 25 years
Total monthly cost
- Mortgage payment (monthly equivalent)
- $46,939
- Property tax
- $3,087
- Condo / maintenance fees
- $0
- Heating
- $0
- Estimated monthly cost
- $50,026
Add your own property tax, condo fees, and heating on the left for a sharper total.
One-time closing costs
- Ontario land transfer tax
- $261,350
- Toronto municipal land transfer tax
- $481,150
- Estimated closing costs
- $742,500
Plus your down payment of $2,199,000. 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
- $2,816,323
- Principal paid down
- $1,120,173
- Interest paid
- $1,696,151
- Balance remaining
- $7,675,827
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.