27 Hillsboro Ave
Annex, Toronto, Ontario M5R 1S6
- Bedrooms
- 5+1
- Bathrooms
- 3
- Size
- 1,500–2,000sq ft
- Per sq ft
- $1,017at the range’s middle
- Lot
- 25 x 80 ft
- Tax a year
- $10,1732025 tax year
- Built
- 100+
- Parking
- 2none
- Days on market
- Members
The brief
About 27 Hillsboro Ave
27 Hillsboro Ave is a 5+1-bedroom, 3-bathroom duplex in Annex, Toronto, listed for sale at an asking price of $1,779,000 (MLS® C14144160).
27 Hillsboro Avenue Opportunity Meets Lifestyle in the Heart of Avenue & DavenportWelcome 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. Main level freshly updated with new flooring, paint, and modern lighting. Lower level recently updated, new windows and water proofing.currently leased. Each upper level enjoys its own private porch and includes a sun porch, offering wonderful bonus family space, a home office, or a cozy reading retreatThe basement in-law suite currently leased.Laundry and utilities are shared, keeping operations straightforwardFrom 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 potentialAn initial zoning review 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.
Insights
Condition Score
Good73/1001 documented update signal
Source: Listing age, structured features and disclosed update language; not an inspection.
Cashflow Quality
Shortfall27/100−$2,965/mo against the cost of owning (20% down, 4.8%, 25 yrs)
Source: Median of 60 homes with 6 bedrooms for lease in Toronto right now. Cost of owning counts the mortgage and property tax.
Condition uses listing-record signals, not an inspection.
The home
Key facts
- Tax
- $10,173 / 2025
- MLS® number
- C14144160
- Board
- TRREB MLS®
- Property Type
- Duplex
- Building Age
- 100+
- Days on market
- Size
- 1500-2000 sqft
- Lot Size
- 25 x 80 ft
- Listed on
- Parking
- None, 2 Parking
Property details
Property
- Property Type
- Duplex
- Style
- 2-Storey
- Community
- Annex
- Municipality
- Toronto
Building
- Size
- 1500-2000 sqft
- Building Age
- 100+
- Construction
- Brick
Inside
- Bedrooms
- 5+1
- Bathrooms
- 3
- Bathroom Details
- 1 × 4pc Bsmt, 1 × 4pc Main, 1 × 4pc Upper
- Basement Type
- Apartment
- Kitchens
- 2
Parking
- Driveway
- Mutual
- Garage Type
- None
- Additional Parking
- 2
- Total Parking
- 2
Utilities
- Water
- Municipal
- Cooling
- Window Unit
- Heating Type
- Water
Land
- Sewer
- Sewers
- Frontage
- 25 ft
- Depth
- 80 ft
- Lot Size
- 25 x 80 ft
Additional
- Foundation
- Concrete
- Roof
- Asphalt Rolled
- Fireplace
- Yes
- Pool
- None
- Den
- No
- Family room
- No
- Extras
- All appliances where located in as is conditions. All ELF's and window covering where they exist. W/D in basement (new 2024/25) Window A/C units in place in main and upper unit. New boiler 2022, Hot water heater leased $30/month.
Rooms
| Room | Size | Features | Level |
|---|---|---|---|
| Living | 3.02 × 4.5 m | Fireplace | Main |
| Dining | 3.02 × 4.5 m | Window | Main |
| Kitchen | 2.28 × 2.88 m | Window | Main |
| Br | 2.52 × 3.19 m | Window | Main |
| 2nd Br | 2.54 × 3.82 m | Window | Main |
| Living | 3.0 × 4.49 m | Window | Upper |
| Dining | 2.65 × 2.79 m | Window | Upper |
| Kitchen | 2.29 × 2.9 m | — | Upper |
| Primary | 3.0 × 4.49 m | Fireplace, W/O To Balcony | Upper |
| 2nd Br | 2.44 × 3.85 m | Window | Upper |
| 3rd Br | 2.49 × 3.19 m | Window | Upper |
| Living | 2.74 × 4.67 m | Window | Lower |
| Kitchen | 2.78 × 3.95 m | Eat-In Kitchen | Lower |
| Br | 3.42 × 5.33 m | Window | Lower |
| Utility | 2.99 × 6.35 m | Combined W/Laundry, Window | Lower |
Listing history
Buy/sell history for 27 Hillsboro Ave, Toronto, Ontario
Sale history on this site covers the last 2 years, the window permitted under the TRREB MLS® VOW agreement.
| Date Start | Date End | List Price | Price | Event | Listing ID |
|---|---|---|---|---|---|
| Date StartN/A | N/A | $1,779,000 | N/A | For Sale | C14144160 |
Members see the full history. Prices are hidden from signed-out visitors.
The numbers
Mortgage Calculator
Plan with the current asking price
CMHC insurance: not required at 20% down. Payments use Canadian semi-annual compounding.
Mortgage Details
4.8% · 5-year term · 25-year amortization · 20% down
- Total down payment
- $355,800
- Total mortgage amount
- $1,423,200
- Total interest payment
- $1,011,900
- Total purchase cost
- $2,790,900
- Mortgage payment
- $8,117/mo
Cash Flow Analysis
If you rented this home out at 20% down
Break-even down payment
49%Monthly carrying cost
$8,965- Rent $6,000
- Shortfall $2,965
Rental income opens at $6,000, the median asking rent of 60 comparable homes for lease in Toronto. Type over it with the rent you expect. This is a planning tool, not advice.
Land transfer tax on this home
- Ontario land transfer tax
- $32,055
- Toronto municipal land transfer tax
- $32,055
- Total land transfer tax
- $64,110
- First-time buyer rebates (Ontario up to $4,000 + Toronto up to $4,475)
- −$8,475
- Total for first-time buyers
- $55,635
See how this is worked out
- 0.5% on the first $55,000
- $275
- 1.0% from $55,000 to $250,000
- $1,950
- 1.5% from $250,000 to $400,000
- $2,250
- 2.0% from $400,000 to $1,779,000
- $27,580
- Ontario total
- $32,055
Toronto’s municipal tax uses the same brackets at this price, so it adds another $32,055.
An estimate at the asking price, for a home with one or two single-family residences. Your lawyer confirms the exact amount.
Estimate
Estimated value requires sign in
Market estimates use sold comparables and are available after you sign in and accept MLS® VOW terms.
The estimate is an automated value built from public and MLS® data. It is not an appraisal; ask Yossi Kaplan, MBA, Salesperson for a full comparative market analysis.
Comparable sales
Comparable sales require sign in
Closing prices and sold comps are available to registered visitors who accept MLS® VOW terms on this site.
The land
Lot
- Lot area
- 2,000 sq ft186 m²
- Street frontage
- 25 ft7.6 m
- Depth
- 80 ft24.4 m
The area is the frontage multiplied by the depth, so boundaries are approximate. Confirm with a survey before you buy.
Source: the MLS® listing record.
Land and environment
Public records about this location. Not part of the MLS® listing and not provided by the listing brokerage.
Water and conservation4
- Not in Toronto and Region Conservation Authority’s mapped regulated areaAt the address
- No mapped wetland within 120 m120 m
- No water-supply well recorded within 250 m21 test or monitoring holes also recorded.250 m
- Groundwater recorded about 15.1 m below ground nearbyThe middle water level in the well records within 500 m (256 records). It changes with the season and from spot to spot.500 m
Toronto and Region Conservation Authority · Province of Ontario open data
Planning and building activity5
- Outside the Greenbelt, Oak Ridges Moraine and Niagara Escarpment plan areasAt the address
- 49 building permits issued within 250 m in the last 2 years250 m
- 2 open development applications within 250 mAn application is a proposal: it may change, be refused or never be built.250 m
- Nearest airport: 4.5 km4.5 km
- Mapped parcel: about 1,680 sq ftMeasured from the municipal parcel map, which can differ from the survey and from the lot size in the listing.At the address
Province of Ontario open data · Municipal building permits · Municipal development applications · toronto.parcels
Around the home2
- Nearest rail line: 490 m490 m
- A trail on the Ontario trail network within 1 km1 km
Province of Ontario open data
Environmental records4
- No licensed pit or quarry within 2 km2 km
- No recorded oil, gas or salt well within 250 m250 m
- No facility within 1 km reports pollutant releases to Environment CanadaThe nearest is The Governing Council of the University of Toronto — St George Campus, 1.6 km away. Only facilities above the inventory’s reporting thresholds are listed.1 km
- No federal contaminated site within 1 kmThe federal inventory covers federal land only; it says nothing about provincial or private sites.1 km
Province of Ontario open data · Government of Canada open data
Power and internet3
- Electricity is distributed here by Toronto Hydro-Electric System LimitedAt the address
- Wired internet 50/10 Mbps or faster is listed at a household 40 m awayFixed wireless 50/10 Mbps or faster. LTE mobile coverage listed. ISED’s National Broadband Data at the nearest household point (40 m from the listing); 50/10 Mbps is its top category and includes faster plans. Confirm with a provider for this address.40 m
- Across the surrounding area: fibre to the home, cable, DSL internet listedFibre to the home: Beanfield Metroconnect, Bell, Dotto One, FibreStream, Rogers. Cable: Rogers. DSL: Bell. Fixed wireless: Bell, Rogers, Routcom, SkyChoice Communications. Mobile: Bell, Freedom Mobile, Rogers, Telus. Satellite: Xplore. ISED’s list for the surrounding ~25 km² area; check with a provider for this address.Area-wide
Ontario Energy Board · Innovation, Science and Economic Development Canada
Each record is placed at the distance its own line states. None of it is an inspection of the property. Confirm anything that matters to you with the municipality, Toronto and Region Conservation Authorityor the record’s publisher.
Contains information licensed under the Open Government Licence – Canada. Contains information licensed under the Open Government Licence – Ontario. Contains information licensed under the Open Government Licence – Toronto. Contains information made available under the Toronto and Region Conservation Authority Open Data Licence v1.0.
Heritage and ravine protection
- Not found on the Heritage Register
- Not in a mapped Heritage Conservation District
- Not in the mapped ravine protection area
What this means: None of these City records was found at this address. That does not rule out other approvals, such as a conservation authority permit, so check before you plan work.
City of Toronto Heritage Register, Heritage Conservation Districts and the Ravine and Natural Feature Protection by-law, read at this address from the City’s maps. Contains information licensed under the Open Government Licence – Toronto.
Zoning
Zone
R (f5.0; d1.0) (x485)By-law
569-2013Municipality
Toronto1 f5.0
Frontage: at least 5.0 m.
2 d1.0
Density: floor area is capped at 1.0 times the lot area.
3 x485
Site-specific exception 485: this site has rules of its own, written in the by-law.
4 Where this is written
Chapter 10, section 10.10 of By-law 569-2013 · Exception 900.2.10(485)
5 What that means in practice
These are the zone’s rules, not permission for this lot. What can be built also depends on the exceptions, overlays and setbacks that apply here. Confirm with the City before you plan.
City of Toronto Zoning By-law 569-2013, read at this address from the City’s zoning map. Open the City’s zoning map. Contains information licensed under the Open Government Licence – Toronto.
Permit history
No building permits on file at this address.
Signals around this home
Changing nearby. 6 open development applications within 800 m of this home.
100 DAVENPORT RDSite planAppeal Received
Site Plan Approval application to facilitate the redevelopment of the site for a 19-storey mixed-use building having a non-residential gross floor area of 441.96 square metres, and a residential gross floor area of 10,296.40 square metres. A total of 43 residential dwelling units are proposed.
200 m away100 DAVENPORT RDCondominiumUnder Review
*** Draft Plan of Condominium for 42 residential dwelling units.
200 m away109 PEARS AVESite planUnder Review
Site Plan Approval for an 11-storey mixed-use building containing 18 dwelling units and 400 square metres of non-residential gross floor area.
310 m away111 PEARS AVESite planUnder Review
Site Plan Approval for an 11-storey mixed-use building containing 18 dwelling units and 400 square metres of non-residential gross floor area.
320 m away185 AVENUE RDSite planUnder Review
Site Plan Approval for an 11-storey mixed-use building containing 18 dwelling units and 400 square metres of non-residential gross floor area.
320 m away183 AVENUE RDSite planUnder Review
Site Plan Approval for an 11-storey mixed-use building containing 18 dwelling units and 400 square metres of non-residential gross floor area.
330 m away
City of Toronto Open Data — Development Applications and Building Permits (cleared permits since 2017). An application is a proposal: it may change, be refused or never be built. Contains information licensed under the Open Government Licence – Toronto.
The market
Market area · filters apply to the charts below
The street
Transit nearby
| Station | Lines | Distance |
|---|---|---|
| Rosedale Station | TTC subway: Line 1 Yonge-University | 350 m |
| Bay Station | TTC subway: Line 2 Bloor-Danforth | 600 m |
| Bloor-Yonge Station | TTC subway: Line 1 Yonge-University, Line 2 Bloor-Danforth | 700 m |
| Eglinton Station | TTC subway: Line 1 Yonge-UniversityTTC light rail: Line 5 Eglinton | 3.4 km |
| Union Station | TTC subway: Line 1 Yonge-UniversityGO Transit train: Barrie, Kitchener, Lakeshore East, Lakeshore West, Milton, Richmond Hill, StouffvilleUP Express train | 3.5 km |
The nearest subway, light rail, train, bus rapid transit stations 5 km, as the crow flies. Source: TTC schedule data (GTFS) from the Toronto Transit Commission under the Open Government Licence – Toronto; GO Transit and UP Express schedule data (GTFS) from Metrolinx under the Open Government Licence – Ontario – Metrolinx, downloaded October 18, 2026. Contains information licensed under the Open Government Licence – Toronto. Data used in this product or service is provided with the permission of Metrolinx. Metrolinx makes no representations or warranties of any kind, express or implied, with respect to the Data and assumes no responsibility for the accuracy or currency of the data used in this product or service. Contains information licensed under the Open Government Licence – Ontario – Metrolinx.
Schools nearby
| Elementary | Type | Distance | EQAO average 2024–25 |
|---|---|---|---|
| Jesse Ketchum Junior and Senior Public SchoolToronto DSB | Public · grades JK–8 | 250 m | 89%Grade 6 average |
| Cottingham Junior Public SchoolToronto DSB | Public · grades JK–6 | 600 m | 100%Grade 6 average |
| Our Lady of Perpetual Help Catholic SchoolToronto CDSB | Catholic · grades JK–8 | 1.5 km | 92%Grade 6 average |
| École élémentaire Gabrielle-RoyConseil scolaire Viamonde | French-language public · grades JK–6 | 2.7 km | 96%Grade 6 average |
| Secondary | Type | Distance | Grade 9 math 2024–25 |
|---|---|---|---|
| St Joseph's College SchoolToronto CDSB | Catholic · grades 9–12 | 1.3 km | 66%Grade 9 math |
| Msgr Fraser College (Isabella Campus)Toronto CDSB | Catholic · grades 9–12 | 1.4 km | — |
| Jarvis Collegiate InstituteToronto DSB | Public · grades 9–12 | 1.6 km | 34%Grade 9 math |
| Collège français secondaireConseil scolaire Viamonde | French-language public · grades 9–12 | 1.9 km | 86%Grade 9 math |
EQAO: share of students at or above the provincial standard, 2024–25 (Ontario open data). These are the schools nearest this home, not the schools it is assigned to: boundaries change, and some schools take students by application. Confirm with the board before you buy. Contains information licensed under the Open Government Licence – Ontario.
The verdict
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