Welcome to the ultimate resource for finding homes in Midtown Toronto, one of the city’s most vibrant and centrally-located neighborhoods. Our extensive listings feature a diverse selection of properties, perfect for families, professionals, and investors looking for a lively community with easy access to all Toronto has to offer. Discover the unique appeal of Midtown Toronto and find your ideal home with our curated selection, detailed information, and expert guidance.

Login with:

Forgot password Extend Verify Contact Signup Login

27 Hillsboro Avenue

Annex Toronto M5R 1S6

$1,799,000

Residential Freehold beds: 5+1 baths: 3.0

Share on X

Share on Facebook

Share on Pinterest

Share Link

Share on Twitter

Share on Facebook

Share on Pinterest

Share Link

• Details
• Photos
• Videos
• Map

Status:

Active

Prop. Type:

Residential Freehold

MLS® Num:

C12870052

Bedrooms:

5+1

Bathrooms:

3

• Photos (37)

Schedule a viewing:

in-person virtual

---

ASAP

Mon

6

APR

Tue

7

APR

Wed

8

APR

Thu

9

APR

Fri

10

APR

Sat

11

APR

Sun

12

APR

Cancel any time.
• Schedule / Email
• Send listing
• Mortgage calculator
• Print listing

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.

General Info:

Property Type:

Residential Freehold

Property Sub Type:

Duplex

Home Style:

2-Storey

Approx. Age:

100+

Total Approx Floor Area:

1500-2000

Lot Depth:

80'24.4 m

Lot Frontage:

25'7.62 m

Direction Faces:

South

Bedrooms:

5+1

Bathrooms:

3.0

Water supply:

Municipal

Kitchens:

3

Kitchens in Basement:

1

Bedrooms Above Grade:

5

Bedrooms Below Grade:

1

Kitchens Above Grade:

2

Rooms Above Grade:

11

Rooms Below Grade:

4

Additional Info:

Heating type:

Water

Heating Fuel:

Gas

Fireplaces:

2

Foundation:

Concrete

Roof:

Asphalt Rolled

Basement:

Apartment, Finished, Separate Entrance

Fireplace Features:

Wood

Fireplace/Stove:

Yes

Garage:

None

Garage Spaces:

0.0

Parking Features:

Mutual

Parking Spaces:

0

Total Parking Spaces:

2.0

Family Room:

No

Possession Details:

Immediate

Pool:

None

Financial Info:

HST Applicable To Sale Price:

Included In

Taxes:

$10,173 / 2025

Assessment:

$- / -

County:

Toronto

Listing Area:

Toronto C02

Listing Sub-Area:

Annex

Property Features / Area Influences:

Library, Park, Place Of Worship, Public Transit, Rec./Commun.Centre, School

Interior Features:

In-Law Capability, Water Heater Owned

Exterior Features:

Awnings, Porch

Rental Items:

Hot water heater

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.

Exclusions:

None

Exterior Finish:

Brick

View:

Park/Greenbelt

Room Information:

Floor

Type

Size

Other

Main

Living Room

14'9"4.50 m × 9'11"3.02 m

Fireplace

Main

Dining Room

14'9"4.50 m × 9'11"3.02 m

Window

Main

Kitchen

9'5"2.87 m × 7'5¾"2.28 m

Window

Main

Bedroom

10'6"3.20 m × 8'3¼"2.52 m

Window

Main

Bedroom 2

12'6"3.81 m × 8'4"2.54 m

Window

Upper

Living Room

14'8¾"4.49 m × 9'10"3.00 m

Window

Upper

Dining Room

9'2"2.79 m × 8'8"2.64 m

Window

Upper

Kitchen

9'6"2.90 m × 7'6"2.29 m

Upper

Primary Bedroom

14'8¾"4.49 m × 9'10"3.00 m

Fireplace, W/O To Balcony

Upper

Bedroom 2

12'8"3.86 m × 8'2.44 m

Window

Upper

Bedroom 3

10'6"3.20 m × 8'2"2.49 m

Window

Lower

Living Room

15'4"4.67 m × 9'2.74 m

Window

Lower

Kitchen

12'11½"3.95 m × 9'1½"2.78 m

Eat-in Kitchen

Lower

Bedroom

17'6"5.33 m × 11'3"3.43 m

Window

Lower

Utility Room

20'10"6.35 m × 9'10"3.00 m

Combined w/Laundry, Window

Other Details:

Utilities Cable:

Available

Utilities Telephone:

Available

Utilities Gas:

Yes

Utilities Hydro:

Yes

Utilities Water:

Yes

Sewers:

Yes

Special Designation:

Unknown

Sewers:

Sewer

Air Conditioning:

Window Unit(s)

Central Vacuum:

No

Seller Property Info Statement:

No

Listing Info:

Date Listed:

Mar 11, 2026

Original Price:

Signup

Previous Price:

Signup

• 
  Photo 1 of 37
• 
  Photo 2 of 37
• 
  Photo 3 of 37
• 
  Photo 4 of 37
• 
  Photo 5 of 37
• 
  Photo 6 of 37
• 
  Photo 7 of 37
• 
  Photo 8 of 37
• 
  Photo 9 of 37
• 
  Photo 10 of 37
• 
  Photo 11 of 37
• 
  Photo 12 of 37
• 
  Photo 13 of 37
• 
  Photo 14 of 37
• 
  Photo 15 of 37
• 
  Photo 16 of 37
• 
  Photo 17 of 37
• 
  Photo 18 of 37
• 
  Photo 19 of 37
• 
  Photo 20 of 37
• 
  Photo 21 of 37
• 
  Photo 22 of 37
• 
  Photo 23 of 37
• 
  Photo 24 of 37
• 
  Photo 25 of 37
• 
  Photo 26 of 37
• 
  Photo 27 of 37
• 
  Photo 28 of 37
• 
  Photo 29 of 37
• 
  Photo 30 of 37
• 
  Photo 31 of 37
• 
  Photo 32 of 37
• 
  Photo 33 of 37
• 
  Photo 34 of 37
• 
  Photo 35 of 37
• 
  Photo 36 of 37
• 
  Photo 37 of 37

Virtual Tour

Larger map options:

Larger map Satellite map Street View Walkscore

Listed by ROYAL LEPAGE SIGNATURE REALTY

Data was last updated April 5, 2026 at 04:15 AM (UTC)

• DARYL KING
• RE/MAX HALLMARK REALTY LIMITED
• 1 (905) 9075464
• homes@darylking.com

This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.

powered by myRealPage.com

Explore Homes for Sale in Midtown Toronto

Browse our comprehensive listings of homes for sale in Midtown Toronto, offering a variety of styles, sizes, and price points to suit your needs. Each listing includes detailed descriptions, high-quality photos, and essential information to help you make an informed decision. Whether you’re looking for a modern condo, a charming townhouse, or a spacious family home, our listings cater to all preferences and budgets.

Navigating the Home Buying Process in Midtown Toronto

Buying a home in Midtown Toronto involves various considerations, such as understanding the local market, financing options, and neighborhood amenities. Our resources and expert guidance are designed to help you navigate these complexities, ensuring a smooth and informed buying process. We offer advice on home inspections, mortgage options, and long-term investment strategies to help you make the best choice.

Maximizing Exposure for Your Midtown Toronto Home

If you’re selling a home in Midtown Toronto, our platform offers exceptional exposure to a targeted audience of potential buyers. We utilize advanced marketing techniques to highlight the key features and benefits of your property, ensuring it stands out in the competitive Toronto real estate market. Our goal is to connect you with interested buyers efficiently, facilitating successful and profitable transactions.

Start Your Home Search in Midtown Toronto Today

Embark on your journey to find the perfect home in Midtown Toronto with us. Our user-friendly platform and dedicated team are here to assist you every step of the way, making the search and purchase process seamless and rewarding.

Explore our listings and discover the ideal home for your next move or investment. Let us help you find your perfect property in Midtown Toronto.

Explore More Real Estate Options in Toronto:

• New Homes in Toronto
• Lofts in Toronto
• Luxury Penthouses in Toronto
• Cheap Houses in Toronto
• Condos for Rent in Toronto
• Toronto Townhomes for Sale
• Toronto Bungalows for Sale
• Luxury Homes in Toronto
• Toronto Detached Homes
• Toronto Real Estate Listings
• Homes for Sale in Leslieville
• Homes for Sale in Rosedale, Toronto
• Homes for Sale in Leaside, Toronto
• East York Homes for Sale in Toronto

Each of these links will redirect you to a dedicated subpage with detailed listings and information tailored to that specific area. Start exploring and find the home that best suits your needs and preferences.