27 Hillsboro Avenue, Toronto, ON
Annex, Toronto · MLS® C13437452
About this home
27 Hillsboro Avenue Opportunity Meets Lifestyle in the Heart of Avenue & Davenport. Welcome to a rare and versatile offering in one of Toronto's most coveted neighbourhoods. 27 Hillsboro Avenue is a duplex-zoned property with exceptional flexibility for investors, end-users, or visionaries looking to unlock long-term value in this century brick home. The home features a shared driveway with parking for two vehicles a true bonus for this location. All units are vacant, The upper two units have been freshly updated with new flooring, paint, and modern lighting, and are move-in ready or easily rentable. Each upper level enjoys its own private porch, and both feature wood-burning fireplaces, adding warmth and character that tenants and homeowners love.The upper unit also includes a sun porch, offering wonderful bonus family space, a home office, or a cozy reading retreat.The basement in-law suite can be used to provide immediate income from day one. Laundry and utilities are shared, keeping operations straightforward. From a future-planning perspective, the options here are compelling: Keep the current duplex configuration with basement suite,Restore to a stunning single-family home (all stairways are intact),Upgrade or reposition the property to maximize its potential An initial zoning review by Property Pathways indicates potential 6-plex compliance (buyers to confirm independently), making this an exciting prospect for those exploring gentle density and long-term development upside.All of this is wrapped in an unbeatable location: steps to Ramsden Park, minutes to Rosedale subway station, and a short walk to Yorkville, with its world-class dining, shopping, and culture.Live in it. Rent it. Reimagine it. This is a property that grows with your goals-and opportunities like this on Hillsboro Avenue don't come around often. Book your showing and explore the possibilities.
Key facts
- Property type
- Other, 2-Storey
- MLS®
- C13437452
- Bedrooms
- 6 (5 + 1)
- Bathrooms
- 3
- Size
- 1500-2000
- Lot
- 25 × 80 ft
- Cross streets
- Davenport and Avenue
- Parking
- 2 parking
- Driveway
- Mutual
- Basement
- Apartment, Finished, Separate Entrance
- Kitchens
- 3 (2 + 1)
- Heating
- Water
- A/C
- Window Unit(s)
- Exterior
- Brick
- Foundation
- Concrete
- Roof
- Asphalt Rolled
- Sewer
- Sewer
- Property tax
- $10,173 / 2025
- Days on market
- 41
- Listing brokerage
- ROYAL LEPAGE SIGNATURE REALTY
Rooms
Window
Window
Eat-in Kitchen
Window
Window
Window
fireplace · w/o to balcony
Window
Window
Window
Fireplace
combined w/laundry · window
Window
Window
Listed at $1,799,000, and my independent estimate is about 19% above what comparable homes suggest.
In Annex lately, sellers get about 98% of asking; homes sell in ~31 days.
Total price vs nearby homes. Fair value about $1.52M, median of 14 comparables.
How this estimate is builtthe short version
I take the 14 most comparable recent sales nearby and adjust each one to this home for the real differences (size, beds, baths, garage, and standout features), 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 $1.83M, a bit higher.
What the listing highlights1 point to weigh
Claims from the listing, worth confirming in person. I can book you a private showing.
- Transit / schools nearby: convenience and resale support, verify the exact distances and school catchment. Value driver
Schools & getting aroundcatchment and transit
Its public catchment (Jesse Ketchum Junior and Senior Public School) 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
Priced above comparable homes overall, but the price per square foot ($1,028/sqft) is below the area, so you are paying for extra space rather than a premium.
There were not many closely comparable homes right in Annex, so I widened the search to the surrounding area.
Based on 14 comparable homes that recently sold nearby.
This home lists 29% below the area average of $1,447/sqft.
On the market now.
View comparable listingsPrice per square foot vs the area average.
Neighbourhood & location
Annex, 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.
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 24, 2026); conventional rates run a little higher.
Mortgage amount $1,439,200 · 4.14% over 25 years
Total monthly cost
- Mortgage payment (monthly equivalent)
- $7,680
- Property tax
- $848
- Condo / maintenance fees
- $0
- Heating
- $0
- Estimated monthly cost
- $8,528
Add your own property tax, condo fees, and heating on the left for a sharper total.
One-time closing costs
- Ontario land transfer tax
- $32,455
- Toronto municipal land transfer tax
- $32,455
- Estimated closing costs
- $64,910
Plus your down payment of $359,800. 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
- $460,806
- Principal paid down
- $183,282
- Interest paid
- $277,524
- Balance remaining
- $1,255,918
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
Income potential: the basement has a separate entrance, which often supports a rentable in-law or second suite. That can lift real rent well above the figure above and help carry the mortgage. Ask us about permitted use in this area.
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 ROYAL LEPAGE SIGNATURE REALTY. MLS®/PropTx.