27 Hillsboro Avenue

Annex, Toronto, M5R 1S6
FOR SALE
$1,799,000
27 Hillsboro Avenue, Toronto
27 Hillsboro Avenue
27 Hillsboro Avenue
27 Hillsboro Avenue
27 Hillsboro Avenue
27 Hillsboro Avenue
27 Hillsboro Avenue
27 Hillsboro Avenue
27 Hillsboro Avenue
27 Hillsboro Avenue
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5 + 1
BEDROOMS
3
BATHROOMS
2 + 1
KITCHENS
11 + 4
ROOMS
C13437452
MLSID
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Property Description
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.
Sold History
List Date Sold Date Days Listed List Price Sold Price
2001-05-24 2001-10-31 160 $439,000 $415,000
Nearby Intersections
Property Features
Library, Park, Place Of Worship, Public Transit, Rec./Commun.Centre, School, In-Law Capability, Water Heater Owned, Mutual, Wood
Property Details
Address
27 Hillsboro Avenue
Community
Postal Code
M5R 1S6
Property Type
Duplex, Duplex
Lot Size
25' x 80'
Taxes
$10,173 (2025
Basement
Apartment, Finished, Separate Entrance
Exterior
Awnings, Porch
Heat Type
Water
Heat Source
Gas
Water
Municipal
Garage Type
None
Listing contracted with Royal Lepage Signature Realty
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5+1
BEDS
3
BATHS
$1,448,000
FOR SALE
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4+1
BEDS
3
BATHS
$1,500,000
FOR SALE
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8A Nineteenth Street, Toronto
5
BEDS
3
BATHS
$1,499,000
FOR SALE
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279 Lauder Avenue, Toronto
6
BEDS
4
BATHS
$1,449,000
FOR SALE
An excellent opportunity to acquire a well-performing multi-residential property in Toronto's evolving and highly desirable Oakwood Village neighbourhood. 279 Lauder Ave offers investors a stable, income-generating asset in a community experiencing strong rental demand and ongoing revitalization. This very well-managed property has been meticulously maintained by an experienced owner, reflecting pride of ownership and operational efficiency. Recent upgrades include all windows and blinds, exterior doors, driveway and parking areas, composite back deck, refreshed front deck, front stairs and railings, bathrooms, electrical panels, tankless water heater, and most appliances. Current rents are at market level and investors benefit from a **strong cap rate of 4.65%**, with minimal need for repositioning.Tenants benefit from efficient floorplans and excellent transit access, with the St. Clair streetcar just an 8-minute walk away, connecting seamlessly across the city. The property is also steps from the lively St. Clair West corridor, known for its diverse mix of cafés, restaurants, and local shops, enhancing everyday convenience and lifestyle appeal.This well-managed asset reflects pride of ownership and long-term care, making it an ideal turnkey addition to any investment portfolio. With strong fundamentals, desirable location, and steady income, 279 Lauder Ave is positioned for continued tenant demand and future growth.
58 Forty First Street, Toronto
6+2
BEDS
3
BATHS
$1,599,900
FOR SALE
Beautifully renovated detached triplex on a large 50 x 120 foot lot in an unbeatable Toronto location, offering exceptional income potential for investors or end users looking to live in one unit while generating rental income from the others. This well-maintained property features three self-contained units, including two spacious 3-bedroom suites and a 2-bedroom lower-level apartment, making it an ideal opportunity for multi-generational living or strong cash flow. Each upper unit showcases hardwood flooring throughout, updated kitchens with stone countertops, stainless steel appliances, modern cabinetry and stylish finishes. The thoughtfully designed layouts offer generous living and dining areas, spacious bedrooms and renovated bathrooms. The lower-level apartment provides additional income potential with its own kitchen, living space, 2 bedrooms and full bath. The property also offers a common storage area, coin-operated laundry, a newer hot water tank and no rental items for added peace of mind. Outside, enjoy a detached double-car garage plus parking for up to 8 vehicles-an incredibly rare feature in the city. Conveniently located close to the TTC, GO Train, the lake, parks, schools, and shopping, this turnkey investment combines location, versatility, and outstanding value in one exceptional property. Fully leased with great AAA tenants! Start building equity immediately!
123 Seaton Street, Toronto
4+1
BEDS
4
BATHS
$1,499,000
FOR SALE
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412 Wellesley Street, Toronto
4
BEDS
3
BATHS
$1,399,000
FOR SALE
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4
BEDS
2
BATHS
$1,680,000
FOR SALE
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