21 Fifeshire Road, Toronto, ON
St. Andrew-Windfields, Toronto · MLS® C13250474
About this home
Bespoke Residence Set On A Stunning 121' Wide Manicured Lot Which Stands Among The Finest In Prestigious Estates On The Much Sought After St. Andrew-Windfields Neighborhood. Encompassing Approximately 8,300 Square Feet Of Curated Living Space With Ideal Entertainment Flow, The Residence Is Defined By Imported Marble, Rich Hardwood, Tailored Lighting, And Refined Designer Detailing Throughout. Beyond A Tree-Lined Circular Drive, The Stately 6+1 Bedroom, 9 Bathroom Home Reveals A Grand Foyer Of Striking Elegance, Where A Soaring Cathedral Ceiling With Skylight Bathes The Interiors In Natural Light, Accentuating A Sweeping Natural Stone Staircase With Custom Brass And Wrought Iron Railings. Gracious Formal Living And Dining Rooms, Alongside A Distinguished Library Adorned In Brazilian Redwood, And A Custom Chef's Kitchen, Anchor The Main Level With Timeless Sophistication. A Charming Breakfast Area And Expansive Family Room Seamlessly Extend To The Rear Garden Oasis, Creating An Effortless Setting For Both Intimate Gatherings And Entertaining. The Primary Retreat Is A Sanctuary Unto Itself, Featuring A Tranquil Sitting Area With A Custom Fireplace, His And Hers Walk-In Closets, And Accompanying His-And-Hers Ensuites. Five Additional Bedrooms Complete The Second Level. The Lower Level Offers An Exceptional Extension Of Living Space, Including A Nanny Suite, Oversized Recreation Room, Full Bar, Exercise Room With Ensuite Sauna, Cedar Closet, And A Walk-Up To The Gardens, With Ample Opportunity For Further Customization. Outdoors, The Estate Impresses With A 20' X 40' Pool, Multiple Lounging And Entertaining Areas, An Expansive Stone Terrace, And A Serene Koi Pond, All Enveloped By Lush Landscaping To Ensure Ultimate Privacy. A Rare And Distinguished Offering In One Of The City's Most Coveted Enclaves.
Key facts
- Property type
- Detached, 2-Storey
- MLS®
- C13250474
- Bedrooms
- 6 (5 + 1)
- Bathrooms
- 8 (1 half)
- Size
- 5,000 sq ft
- Lot
- 121.89 × 178.36 ft
- Cross streets
- Bayview Ave and York Mills Rd
- Parking
- 2 garage · 14 parking (built-in)
- Driveway
- Circular Drive
- Basement
- Walk-Up, Finished
- Heating
- Forced Air
- A/C
- Central Air
- Exterior
- Stucco (Plaster)
- Foundation
- Concrete
- Roof
- Shingles
- Sewer
- Sewer
- Pool
- Inground
- Property tax
- $23,377 / 2025
- Days on market
- 42
- Listing brokerage
- RE/MAX REALTRON BARRY COHEN HOMES INC.
Rooms
hardwood floor · overlooks garden · double closet
w/o to terrace · skylight · fireplace
hardwood floor · picture window · overlooks frontyard
wet bar · fireplace · above grade window
closet · overlooks backyard · hardwood floor
breakfast area · centre island · marble floor
hardwood floor · double closet · overlooks frontyard
marble floor · double closet · crown moulding
5 pc ensuite · walk-in closet(s) · combined w/sitting
3 pc ensuite · pot lights · closet
bay window · crown moulding · overlooks living
fireplace · overlooks frontyard · hardwood floor
double closet · hardwood floor · combined w/sitting
Listed at $7,500,000, this home is about 23% above what comparable homes suggest. The number above is my independent estimate of value, not the asking price.
Based on 8 similar homes nearby, adjusted for size, beds, and baths.Median of 8 comparable active listings, adjusted for size, beds, and baths. The city (MPAC) assessment points to about $4.82M, a bit lower.
How I got there
Here is the exact math behind the estimate. I start from the closest comparable listing and adjust for the real differences (size, beds, baths) to land on a like-for-like value for this home.
- Closest comparable, listed at $4.80M
- Bathrooms +$15K
- Adjusts to $4.82M
That comparable adjusts to $4.82M; the $6.09M estimate above is the median of all 8 comparables, which is steadier than any single home.This uses comparable active listings, not sold prices. Lot, condition, and finishes are my in-person call, and I can run a full CMA with recent solds.
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.
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 3-minute walk away.
Total price vs nearby homes. Fair value about $6.09M, median of 8 comparables.
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.
- Upscale kitchen: a genuine value driver, verify the appliances, stone, and finishes in person.
- Pool: lifestyle appeal, but adds maintenance, insurance, and resale is mixed.
- Tall ceilings: they transform how a home feels, worth confirming the actual heights room to room.
- Hardwood floors: quality hardwood is durable and broadly desirable.
- Sold as-is / needs work: budget for renovation, the price should reflect the condition.
- Value driver
- Weigh carefully
- Worth verifying
- 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 homesThis home lists 21% above the area average of $1,243/sqft.
41 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 270 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 18, 2026); conventional rates run a little higher.
Mortgage amount $6,000,000 · 4.14% over 25 years
Total monthly cost
- Mortgage payment (monthly equivalent)
- $32,018
- Property tax
- $1,948
- Condo / maintenance fees
- $0
- Heating
- $0
- Estimated monthly cost
- $33,966
Add your own property tax, condo fees, and heating on the left for a sharper total.
One-time closing costs
- Ontario land transfer tax
- $173,975
- Toronto municipal land transfer tax
- $278,975
- Estimated closing costs
- $452,950
Plus your down payment of $1,500,000. 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
- $1,921,094
- Principal paid down
- $764,101
- Interest paid
- $1,156,992
- Balance remaining
- $5,235,899
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
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 RE/MAX REALTRON BARRY COHEN HOMES INC.. MLS®/PropTx.