21 Fifeshire Road, Toronto, ON
St. Andrew-Windfields, Toronto · MLS® C13250474
About this home
In short
- Bespoke Residence Set On A Stunning 121' Wide Manicured Lot Which Stands Among The Finest In Prestigious Estates On The Much Sought After St.
- Encompassing Approximately 8,300 Square Feet Of Curated Living Space With Ideal Entertainment Flow, The Residence Is Defined By Imported Marble, Rich Hardwood...
- 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...
- A Charming Breakfast Area And Expansive Family Room Seamlessly Extend To The Rear Garden Oasis, Creating An Effortless Setting For Both Intimate Gatherings And...
- 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...
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
- 5+1 (6 total)
- 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
- 98
- 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. My estimate lands at $3.90M, so the ask sits about 92% above what comparable sales suggest. A gap that wide can point to premium finishes, a bigger lot, or simply an ambitious ask, so it is worth a close look at what justifies it before you offer. Treat the figure as a starting point: 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.
A price cut is the likelier next move. 98 days on the market against about 46 for homes like it here, and asking 92% above where comparable closings put it. That is leverage for a buyer: offer with it in mind rather than waiting for the cut, since a reduction brings new eyes with it.
Second read, from the city assessment: $4.05M. Similar homes sold in line with their assessments, and this one lands close to the comparable-sales figure, which is what a firm read looks like.
Total price vs nearby homes. Fair value about $3.90M, median of 73 comparables.
The market behind the math:
About 3.3 months of inventory: 25 detached homes for sale in the area against 23 closings in the last 90 days. Under two months favours sellers, over four favours buyers.
Price per square foot: this home lists at $1,500/sqft against an area asking average of $1,226/sqft. Size and $/sqft both feed the estimate above.
- 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.
- Walk-up basement. Extra light, usable space, and income potential, so the estimate is a conservative floor for it.
How this estimate is builtthe short version
I take the 73 most comparable recent sales nearby and adjust each one to this home for the real differences (size, beds, baths, garage, lot frontage, a ravine backing, an inground pool), then use the median, which is steadier than leaning on any single sale.
It’s grounded in recent closing prices, not asking prices. Lot, condition, and finishes are my in-person call, and the city (MPAC) assessment points to about $4.05M, a close match.
What the listing highlights5 points to weigh
Claims from the listing, worth confirming in person. I can book you a private showing.
- Upscale kitchen: a genuine value driver, verify the appliances, stone, and finishes in person. Value driver
- Pool: lifestyle appeal, but adds maintenance, insurance, and resale is mixed. Weigh carefully
- Tall ceilings: they transform how a home feels, worth confirming the actual heights room to room. Worth verifying
- Hardwood floors: quality hardwood is durable and broadly desirable. Lifestyle
- Sold as-is / needs work: budget for renovation, the price should reflect the condition. Weigh carefully
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 73 comparable homes that sold in St. Andrew-Windfields over the past two years, from 170 closings there.
For sale
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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 $3.90M, which is where my estimate comes from.
Per square foot, these ask about $1,189/sqft; this home lists at $1,500/sqft. Size is part of the price story, not just the sticker.
The 5 closest of 8 active listings nearby.
See all comparable homesNeighbourhood & 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 4.09% via Ratehub.ca (as of September 11, 2026); conventional rates run a little higher.
Mortgage amount $6,000,000 · 4.24% over 25 years
Total monthly cost
- Mortgage payment (monthly equivalent)
- $32,347
- Property tax
- $1,948
- Condo / maintenance fees
- $0
- Heating
- $0
- Estimated monthly cost
- $34,295
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
- $1,940,800
- Principal paid down
- $755,147
- Interest paid
- $1,185,654
- Balance remaining
- $5,244,853
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 numbersThe last 33 whole-home leases in St. Andrew-Windfields signed at a median of $7,041 a month; adjusted to this home for size, beds and baths, and for where rents stood the month each signed, that is $8,112. 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 RE/MAX REALTRON BARRY COHEN HOMES INC.. MLS®/PropTx.