442 Heath Street, Toronto, ON
Leaside, Toronto · MLS® C14127394
About This Home
In short
- Welcome to 442 Heath Street East, an architecturally distinctive contemporary residence offering more than 6,000 square feet across three levels in coveted Bennington...
- Upstairs are four spacious bedrooms, a family library and laundry room, including a spectacular primary retreat with backyard views, a skylit walk-in closet and...
- Discover a gorgeous swimming pool, expansive entertaining patio, outdoor cooking area, children's play treehouse, butterfly garden, outdoor table tennis and...
- Enjoy proximity to Moore Park Ravine, the Beltline Trail, Evergreen Brick Works, parks and Bayview Avenue's shops, cafes and restaurants.
Read the full description
Welcome to 442 Heath Street East, an architecturally distinctive contemporary residence offering more than 6,000 square feet across three levels in coveted Bennington Heights, with interiors by Ashley Botten. Set on an extraordinary lot, this sun-filled home pairs luxurious finishes, thoughtful built-ins, in-floor heating throughout and a heated driveway for year-round comfort. A sleek and stunning entryway features extensive storage and introduces the elegant living and dining room, complete with show-stopping floor-to-ceiling windows. The stunning modern kitchen features a large island and adjoining breakfast area. The expansive family room overlooks the landscaped backyard, while a main-floor office, powder room and attached garage add everyday convenience. Upstairs are four spacious bedrooms, a family library and laundry room, including a spectacular primary retreat with backyard views, a skylit walk-in closet and luxurious five-piece ensuite. The lower level offers a generous recreation room, fifth bedroom, full bathroom, fitness and Pilates studio, infrared sauna and ample storage. And then there is the backyard, which is reminiscent of the most exclusive resorts in the world. Discover a gorgeous swimming pool, expansive entertaining patio, outdoor cooking area, children's play treehouse, butterfly garden, outdoor table tennis and additional green space beyond the pool. Expansive windows bring exceptional natural light into the home and frame its lush surroundings. Enjoy proximity to Moore Park Ravine, the Beltline Trail, Evergreen Brick Works, parks and Bayview Avenue's shops, cafes and restaurants. Nearby schools include Bennington Heights Elementary, Bessborough Drive Elementary and Middle School and Leaside High School (subject to school board policies), with convenient TTC connections, access to downtown and the Don Valley Parkway. A rare blend of modern architecture, family comfort and resort-inspired outdoor living, this home is truly exceptional.
Key Facts
- Property type
- Detached, 2-Storey
- MLS®
- C14127394
- Bedrooms
- 4+1 (5 total)
- Bathrooms
- 5 (1 half)
- Size
- 3500-5000 sq ft
- Lot
- 43 × 240 ft
- Cross streets
- Bayview Ave & Moore Ave
- Parking
- 1 garage · 3 parking (built-in)
- Driveway
- Private
- Basement
- Finished
- Heating
- Forced Air
- A/C
- Central Air
- Exterior
- Brick, Concrete
- Foundation
- Poured Concrete
- Roof
- Flat, Membrane
- Sewer
- Sewer
- Pool
- Inground
- Property tax
- $25,037 / 2026
- Listing brokerage
- ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM
Rooms
See all 15 rooms, floor by floor
Combined w/Dining
heated floor · b/i closet
heated floor · double closet · semi ensuite
fireplace · b/i shelves · w/o to patio
Combined w/Family
heated floor · double closet · semi ensuite
fireplace · w/o to patio
built-in speakers · above grade window
heated floor · pocket doors
Combined w/Living
heated floor · double closet · semi ensuite
heated floor · walk-in closet(s) · 5 pc ensuite
Above Grade Window
heated floor · built-in speakers
Our Take
Team Asgarian · BrokerListed at $9,495,000. Going by how homes in Leaside and the wider GTA have actually closed against their asking prices (about 98%, 30 local closings in 90 days), the likely sale price is near $9.33M, if it sells. A realistic range is $8.74M to $10.51M.
Independent value check: no figure for this home. Going only by the sales record, our model lands more than 25% below the ask. At that distance an automated figure has rarely been close to the eventual sale price, so we are not printing one. The usual reason is something the record cannot show: a rebuild, a second unit, or a lot or setting unlike the homes around it.
Total price vs nearby homes. Likely closing about $9.33M, from 30 recent closings in this pocket.
The market behind the math:
About 0.6 months of inventory: 6 detached homes for sale in the area against 30 closings in the last 90 days. Under two months favours sellers, over four favours buyers.
Price per square foot: this home lists at $2,234/sqft against an area asking average of $1,247/sqft.
- Ravine / green setting. This home is described as backing onto a ravine or green setting. A premium that comparable-sales math under-prices, so read the estimate as a floor.
- 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
This figure comes from a model built on about 44,000 recent GTA sales. It weighs this home’s tax assessment, size, age, location and features against what homes like it actually sold for, including sales in this neighbourhood.
It never sees the asking price. The 30 most comparable recent sales on their own, adjusted for size, beds, baths and lot, point to about $3.57M. Condition and finishes remain an in-person call.
What the listing highlights3 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
- Pool: lifestyle appeal, but adds maintenance, insurance, and resale is mixed. Weigh carefully
- Primary suite: a key comfort and resale feature. Lifestyle
Schools & getting aroundcatchment and transit
On schools, this address is zoned for Bessborough Drive Elementary and Middle 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
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.
Based on 30 comparable homes that sold in Leaside over the past two years, from 218 closings there.
What sellers nearby are asking
For sale in Leaside now · asking prices
Every home like this one for sale in Leaside right now, newest listing first. These are asking prices, not sales.
Per square foot, these ask about $1,296/sqft; this home lists at $2,234/sqft. Size is part of the price story, not just the sticker.
The 5 closest in price of 14 for sale in Leaside.
See all comparable homesSold price trend
Median sold price for detached homes in Leaside: $1.28M in September 2026, down 20% from a year ago, on 111 closings in 11 months.
Line: median sold price, each month averaged with its neighbours and weighted by closings. Bars: closings that month.
Month by month
| Month | Median sold | Closings |
|---|---|---|
| October 2025 | $2.19M | 15 |
| November 2025 | $2.67M | 9 |
| December 2025 | $2.98M | 6 |
| January 2026 | $2.55M | 7 |
| March 2026 | $1.88M | 6 |
| April 2026 | $2.40M | 17 |
| May 2026 | $2.19M | 16 |
| June 2026 | $2.60M | 8 |
| July 2026 | $1.83M | 11 |
| August 2026 | $2.25M | 11 |
| September 2026 | $1.28M | 5 |
Thinking of selling near Leaside?
You have just seen what homes around here are asking. We can tell you what yours would sell for, from the closings on your street, free and with no obligation.
Neighbourhood & 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) →
Schools & catchment
Assigned attendance-boundary schools, with EQAO resultsThe 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.
Questions About 442 Heath Street
What is the asking price for 442 Heath Street?
It is listed at $9,495,000.
How many bedrooms and bathrooms does 442 Heath Street have?
4+1 bedrooms, and 5 bathrooms (1 of them half baths).
How big is 442 Heath Street?
The listing gives 3500-5000 sq ft of living space, on a 43 × 240 ft lot.
Does 442 Heath Street have parking?
1 garage space, 3 parking spaces in all.
What are the property taxes on 442 Heath Street?
$25,037 a year, for 2026.
Is there an offer date for 442 Heath Street?
The listing does not state an offer date.
Which schools is 442 Heath Street zoned for?
By the school boards' attendance boundaries: Bennington Heights Elementary School, Bessborough Drive Elementary and Middle School, Leaside High School and St. Anselm. Boundaries change, so confirm with the board before relying on it.
When was 442 Heath Street listed?
It came on the market on October 29, 2026.
Who is the listing brokerage for 442 Heath Street?
ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM. Team Asgarian can book you a private showing and represent you as the buyer: (416) 837-8000.
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
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 4.44% via Ratehub.ca (as of October 29, 2026); conventional rates run a little higher.
Mortgage amount $7,596,000 · 4.59% over 25 years
Total monthly cost
- Mortgage payment (monthly equivalent)
- $42,423
- Property tax
- $2,086
- Condo / maintenance fees
- $0
- Heating
- $0
- Estimated monthly cost
- $44,509
Add your own property tax, condo fees, and heating on the left for a sharper total.
One-time closing costs
- Ontario land transfer tax
- $223,850
- Toronto municipal land transfer tax
- $388,700
- Estimated closing costs
- $612,550
Plus your down payment of $1,899,000. 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
- $2,545,362
- Principal paid down
- $917,088
- Interest paid
- $1,628,274
- Balance remaining
- $6,678,912
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.
Helpful resources
All information deemed reliable but not guaranteed. For personal, non-commercial use only. Listing courtesy of ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM. MLS®/PropTx.