27 Hillsboro Avenue
Toronto C02, ON
- 6 bed
- 3 bath
- approx. 1500-2000 sqft
- Duplex
- 89 days on market
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.
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Listing Details
- Taxes (2025)
- $10,173
- Listed
- June 12, 2026
Price History
Listing history
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Property
- Style
- 2-Storey
- Age
- 100+
- Construction
- Brick
- Roof
- Asphalt Rolled
- Foundation
- Concrete
- Interior
- In-Law Capability, Water Heater Owned
- Lot Size
- 25 x 80 Feet
Parking
- Garage
- None
- Covered Spaces
- 0
- Total Parking
- 2
Utilities
- Sewer
- Sewer
- Heat Source
- Gas
Location & Legal
- Cross Street
- Davenport and Avenue
- Parcel Number
- 211940410
- Possession
- Immediate
- Occupancy
- Owner+Tenant
Included
- Inclusions
- 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 upper unit. Main level units stored in basement area. New boiler 2022, Hot water heater leased $30/month.
- Rental Items
- Hot water heater
Schools
Elementary
- Jesse Ketchum Junior and Senior Public School0.3 km
Public · Toronto DSB · 535 students
Grade 3 reading: 82% met the provincial standard · Grade 6 math: 71% met the provincial standard
- Cottingham Junior Public School0.6 km
Public · Toronto DSB · 140 students
Grade 3 reading: 100% met the provincial standard · Grade 6 math: 100% met the provincial standard
- Rosedale Junior Public School0.9 km
Public · Toronto DSB · 220 students
Grade 3 reading: 95% met the provincial standard · Grade 6 math: 100% met the provincial standard
Secondary
- St Joseph's College School1.3 km
Catholic · Toronto CDSB · 545 students
Grade 10 literacy: 87% met the provincial standard
- Msgr Fraser College (Isabella Campus)1.4 km
Catholic · Toronto CDSB · 345 students
- Jarvis Collegiate Institute1.6 km
Public · Toronto DSB · 610 students
Grade 10 literacy: 80% met the provincial standard
Straight-line distance. Nearby schools are not necessarily the assigned schools — confirm catchment with the school board. Scores are EQAO provincial test results for 2024-2025.
Community
Postal area M5R
- Population
- 26,197
- Private dwellings
- 16,591
- Median age
- 42
- Average household size
- 1.8
- Median household income
- $86,000
Source: Statistics Canada, 2021 Census of Population, catalogue 98-401-X2021013. Adapted from Statistics Canada. This does not constitute an endorsement by Statistics Canada of this product.
Local market
Residential Freehold in Toronto C02 · last 12 months
- Median sold price
- $1,250,000
- Homes sold
- 729
- Median days on market
- 25
- Sale-to-list price
- 97.1%
Based on 729 recorded sales of residential freehold properties in Toronto C02 over the last 12 months.
Rooms
4-piece on Basement, 4-piece on Main, 4-piece on Upper
Upper
- Bedroom 212'8" x 8'
- Bedroom 310'6" x 8'2"
- Dining Room9'2" x 8'8"
- Kitchen9'6" x 7'6"
- Living Room14'9" x 9'10"
- Primary Bedroom14'9" x 9'10"
Main
- Bedroom10'6" x 8'3"
- Bedroom 212'6" x 8'4"
- Dining Room14'9" x 9'11"
- Kitchen9'5" x 7'6"
- Living Room14'9" x 9'11"
Lower
- Bedroom17'6" x 11'3"
- Kitchen13' x 9'1"
- Living Room15'4" x 9'
- Utility Room20'10" x 9'10"
Listed by
ROYAL LEPAGE SIGNATURE REALTY
Walk Score
Walk
Transit
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Scores by Walk Score®
Location
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Mortgage Calculator
$359,800
Estimated Monthly Payment
$8,838
Land transfer tax
Ontario land transfer tax only. An estimate — not legal or financial advice. Municipal land transfer tax applies in Toronto and is not included.
Investment Analysis
No recent nearby lease data. Enter a rent to see the numbers.
Mortgage: $8,838/mo (20% down, 5.5%)
Taxes: $848/mo · Insurance: $450/mo
Estimates only. Consult a financial advisor.
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