310 Bessborough Drive, Toronto, ON
Leaside, Toronto · MLS® C13538994
About this home
In short
- Some homes are built; the very best are lived in.
- Lovingly maintained by the same family since 2005, this spectacular home underwent a masterful, back-to-the-studsrenovation and thoughtful addition in 2023.
- Balancing warmth and architectural sophistication, the residence sits proudly on an extraordinary, widening double lot (58' expanding to 70'+ at rear, x 140.5' deep)...
- The main level showcases quartersawn rift-cut white oak flooring with herringbone accents, a formal living room with double terrace doors, and a private office...
- A chef's dream, the custom kitchen features Calacatta Oro Anticomarble, a 7' oak apothecary island, a walk-in pantry with coffee bar, and premium Sub-Zero...
Some homes are built; the very best are lived in. For over two decades, this exceptional North Leaside property has been the backdrop to a lifetime of cherished memories. Lovingly maintained by the same family since 2005, this spectacular home underwent a masterful, back-to-the-studsrenovation and thoughtful addition in 2023. Balancing warmth and architectural sophistication, the residence sits proudly on an extraordinary, widening double lot (58' expanding to 70'+ at rear, x 140.5' deep) with mature, landscaped gardens offering absolute privacy in a coveted neighbourhood. Setting a tone of curated luxury are modern ACM Wiedehopf panels, elegant rain chains, andfull-height Marvin and Anderson Architect windows. Inside, sunlight floods through beautifully crafted interiors. The main level showcases quartersawn rift-cut white oak flooring with herringbone accents, a formal living room with double terrace doors, and a private office enclosed by 4 bench-built oak and glass sliding doors. The family room centers on a custom oak slat media wall and wood fireplace, while the dining room features a gas fireplace and walks out to a raised cedar deck. A chef's dream, the custom kitchen features Calacatta Oro Anticomarble, a 7' oak apothecary island, a walk-in pantry with coffee bar, and premium Sub-Zero, Bertazzoni, and Fisher & Paykel appliances. A hardworking mudroom with soaring ceilings and heated porcelain floors provides a seamless secondary entry. Upstairs, vaulted ceilings and skylights illuminate four bedrooms, including a laundry closet and a primary retreat with a private balcony, fireplace, sitting area, dressing room, and a spa-inspired Arabescato marble ensuite. The walk-out lower level offers incredible flexibility with a recreation room, guest suite, full bath, gym, and secondary kitchen. More than a residence, 310 Bessborough Drive is where the next family's story begins.
Key facts
- Property type
- Detached, 2-Storey
- MLS®
- C13538994
- Bedrooms
- 4+1 (5 total)
- Bathrooms
- 4 (1 half)
- Size
- 3000-3500 sq ft
- Lot
- 57.88 × 140.5 ft
- Cross streets
- Bayview Ave & Broadway Ave
- Parking
- 2 garage · 10 parking (attached)
- Driveway
- Boulevard, Private Double
- Basement
- Finished with Walk-Out, Separate Entrance
- Kitchens
- 2 (1 + 1)
- Heating
- Forced Air
- A/C
- Central Air
- Exterior
- Brick
- Foundation
- Concrete
- Roof
- Asphalt Shingle, Flat
- Sewer
- Sewer
- Property tax
- $15,625 / 2025
- Days on market
- 62
- Listing brokerage
- CHESTNUT PARK REAL ESTATE LIMITED
Rooms
plank · semi ensuite · b/i closet
plank · vaulted ceiling(s) · b/i closet
b/i closet · marble counter
centre island · marble counter · b/i appliances
heated floor · bidet · soaking tub
walk through · hardwood floor · b/i shelves
stone floor · marble counter · 4 pc bath
heated floor · stone floor · closet
heated floor · walk-in closet(s) · walk-in closet(s)
w/o to terrace · french doors · sliding doors
heated floor · hardwood floor · floating stairs
w/o to terrace · french doors · hardwood floor
plank · large window
b/i shelves · hardwood floor · pot lights
w/o to deck · french doors · combined w/family
balcony · vaulted ceiling(s) · gas fireplace
heated floor · stone floor · b/i shelves
Listed at $4,707,000. My estimate lands at $3.32M, so the ask sits about 42% 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. 62 days on the market against about 25 for homes like it here, and asking 42% 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: $3.28M. 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 $3.32M, median of 42 comparables.
The market behind the math:
About 1.1 months of inventory: 9 detached homes for sale in the area against 24 closings in the last 90 days. Under two months favours sellers, over four favours buyers.
Price per square foot: this home lists at $1,448/sqft against an area asking average of $1,465/sqft. Size and $/sqft both feed the estimate above.
- Walk-out basement apartment features. A finished 1 bed walk-out basement apartment with a separate entrance and a second kitchen. A self-contained space for extended family, guests or potential income. In Leaside basements rarely rent out (2 of 81 recent detached leases were basement units), so buyers here treat a suite as family or nanny space rather than income. Value it for the living space, not the rent. Second-suite retrofit status is not verified. A buyer intending to rent should confirm requirements with the City of Toronto.
How this estimate is builtthe short version
I take the 42 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 $3.28M, 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.
- Renovated / rebuilt: recent work can mean fewer upfront costs, worth confirming the scope, quality, and that permits were pulled. Value driver
- Addition / added square footage: more space lifts value when it is permitted and well integrated, verify the permits. Value driver
- Upscale kitchen: a genuine value driver, verify the appliances, stone, and finishes in person. Value driver
- Tall ceilings: they transform how a home feels, worth confirming the actual heights room to room. Worth verifying
- Premium lot / gardens: lot size and privacy hold value and cannot be changed, verify frontage, depth, and any easements. Value driver
Schools & getting aroundcatchment and transit
On schools, this address is zoned for Leaside High School, 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.
Read this with carewhy it’s an estimate, not an appraisal
Priced above comparable homes overall, but the price per square foot ($1,448/sqft) is in line with the area, so you are paying for extra space rather than a premium.
There were not many closely comparable homes right in Leaside, so I widened the search to the surrounding area.
Based on 42 comparable homes that sold in Leaside over the past two years, from 222 closings there.
Nothing 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 $3.32M, which is where my estimate comes from.
Per square foot, these ask about $1,480/sqft; this home lists at $1,448/sqft. Size is part of the price story, not just the sticker.
The 4 closest active listings nearby.
See all comparable homesNeighbourhood & location
Leaside, 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 $3,765,600 · 4.24% over 25 years
Total monthly cost
- Mortgage payment (monthly equivalent)
- $20,301
- Property tax
- $1,302
- Condo / maintenance fees
- $0
- Heating
- $0
- Estimated monthly cost
- $21,603
Add your own property tax, condo fees, and heating on the left for a sharper total.
One-time closing costs
- Ontario land transfer tax
- $104,150
- Toronto municipal land transfer tax
- $128,290
- Estimated closing costs
- $232,440
Plus your down payment of $941,400. 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
- $1,218,046
- Principal paid down
- $473,930
- Interest paid
- $744,116
- Balance remaining
- $3,291,670
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
About the suite: in Leaside basements rarely rent out (2 of 81 recent detached leases were basement units), so the figure above does not count it as income. Buyers here use a suite as family or nanny space.
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 9 whole-home leases in Leaside signed at a median of $7,358 a month; adjusted to this home for size, beds and baths, and for where rents stood the month each signed, that is $8,970. 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 CHESTNUT PARK REAL ESTATE LIMITED. MLS®/PropTx.