27 Old Yonge Street, Toronto, ON
Bridle Path-Sunnybrook-York Mills, Toronto · MLS® C13697434
About this home
In short
- An Exceptional Opportunity To Build Your Dream Residence On This Premium, Mostly Table, One-Acre Building Lot With 300' Of Frontage, Elegantly Perched Atop Its Ridge...
- Conceptual Architectural Renderings By Renowned Architect Stan Makow Illustrate The Extraordinary Potential To Create A Residence Of Approximately 5,300 Square Feet...
An Exceptional Opportunity To Build Your Dream Residence On This Premium, Mostly Table, One-Acre Building Lot With 300' Of Frontage, Elegantly Perched Atop Its Ridge And Commanding Picturesque Ravine Vistas Of The Valley Below. This Remarkable Setting Affords A Rare Combination Of Complete Privacy While Simultaneously Showcasing Sweeping City Views, Including The Iconic CN Tower Skyline. Nestled Within The Esteemed Enclave Of Hogg's Hollow, This Distinguished Property Presents An Exquisite Canvas For A Custom Residence Designed In Refined Harmony With Its Natural Surroundings And Serene Seclusion. Conceptual Architectural Renderings By Renowned Architect Stan Makow Illustrate The Extraordinary Potential To Create A Residence Of Approximately 5,300 Square Feet As Of Right, With The Possibility Of Significantly Greater Scale Through A Committee Of Adjustment Application. Whether You Choose To Design And Build A Bespoke Masterpiece Tailored To Your Exacting Standards, Or Thoughtfully Refine And Expand The Existing Residence With Its Current Abundance Of Character And Enduring Charm, The Opportunity Is Truly Exceptional. A Rare And Distinguished Offering For Builders, Investors, Or End-Users Seeking To Craft A Singular Estate In One Of Toronto's Most Coveted Neighbourhoods. Moments To Fine Shops, Upscale Dining, Premier Golf, Subway Access, And Major Highways. Proudly Held By The Same Family For Generations, This Property Awaits Its Owner-An Invitation To Create Something Truly Remarkable.
Key facts
- Property type
- Detached, 2 1/2 Storey
- MLS®
- C13697434
- Bedrooms
- 4
- Bathrooms
- 3
- Size
- 3500-5000 sq ft
- Lot
- 331 × 200 ft
- Cross streets
- Old Yonge St & York Mills Rd
- Parking
- 3 parking
- Driveway
- Private
- Basement
- Full, Unfinished
- Heating
- Water
- A/C
- None
- Exterior
- Brick, Stucco (Plaster)
- Foundation
- Unknown
- Roof
- Unknown
- Sewer
- Sewer
- Pool
- Inground
- Property tax
- $32,554 / 2025
- Days on market
- 19
- Listing brokerage
- RE/MAX REALTRON BARRY COHEN HOMES INC.
Rooms
vaulted ceiling(s) · hardwood floor · window
eat-in kitchen · w/o to deck · large window
3 pc ensuite · closet
closet · hardwood floor · bow window
closet · hardwood floor · 4 pc bath
closet · hardwood floor · window
bow window · hardwood floor
vaulted ceiling(s) · hardwood floor · window
fireplace · crown moulding · bay window
bay window · fireplace · hardwood floor
closet · hardwood floor · 3 pc bath
hardwood floor · leaded glass · fireplace
Listed at $5,000,000 with no offer date, so the ask is the seller’s number, and homes priced this way sell close to it. My read is $5.04M, typically $4.32M to $5.63M. Comparable closings on their own put this home around $5.15M, which agrees with the ask, so this is a firm read.
Second read, from the city assessment: $6.57M. That is about 28% above the comparable-sales figure. When my two methods disagree this much, the answer usually sits between them and something about this home is not in the comparables (the lot, the condition, a rebuild). I would want to see it before leaning on either number.
Total price vs nearby homes. Fair value about $5.04M, median of 34 comparables.
The market behind the math:
About 7.3 months of inventory: 34 detached homes for sale in the area against 14 closings in the last 90 days. Under two months favours sellers, over four favours buyers.
Price per square foot: this home lists at $1,176/sqft against an area asking average of $1,742/sqft. Size and $/sqft both feed the estimate above.
- 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
I take the 34 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 $6.57M, higher than the comparables and worth a second look.
What the listing highlights2 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
- Development potential: upside only if zoning permits, verify with the city before relying on it. Worth verifying
Schools & getting aroundcatchment and transit
Its public catchment (York Mills Collegiate Institute) tests around the provincial average, a steady, family-friendly draw. The full EQAO breakdown is below.
Read this with carewhy it’s an estimate, not an appraisal
The listing states size as a wide range, so the size adjustment is approximate and this estimate is a rough read. I can confirm exact square footage to tighten it.
There were not many closely comparable homes right in Bridle Path-Sunnybrook-York Mills, so I widened the search to the surrounding area.
Based on 34 comparable homes that sold in Bridle Path-Sunnybrook-York Mills over the past two years, from 107 closings there.
For sale
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 $5.15M, which is where my estimate comes from.
Per square foot, these ask about $1,151/sqft; this home lists at $1,176/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
Bridle Path-Sunnybrook-York Mills, 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 9, 2026); conventional rates run a little higher.
Mortgage amount $4,000,000 · 4.24% over 25 years
Total monthly cost
- Mortgage payment (monthly equivalent)
- $21,564
- Property tax
- $2,713
- Condo / maintenance fees
- $0
- Heating
- $0
- Estimated monthly cost
- $24,277
Add your own property tax, condo fees, and heating on the left for a sharper total.
One-time closing costs
- Ontario land transfer tax
- $111,475
- Toronto municipal land transfer tax
- $141,475
- Estimated closing costs
- $252,950
Plus your down payment of $1,000,000. 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
- $1,293,867
- Principal paid down
- $503,431
- Interest paid
- $790,436
- Balance remaining
- $3,496,569
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 22 whole-home leases in Bridle Path-Sunnybrook-York Mills signed at a median of $10,500 a month; adjusted to this home for size, beds and baths, and for where rents stood the month each signed, that is $10,157. 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.