As it’s name suggests, Little Italy is a Toronto neighbourhood with a vibrant cultural community. Italian flair mingles with Portuguese influences, and a variety of people from various backgrounds have discovered the benefits of real estate in Little Italy. The area is bordered by Bathurst Street to the east, Ossington to the west, Harbord to the north, and Dundas Street West to the south. College Street runs through the middle of the neighbourhood, with delicious Italian restaurants and fashionable shops. Dundas Street West offers a collection of Portuguese businesses as well as pubs and bars. The area has a cool urban feel, since it is walking distance to Queen West and bohemian favourite, Kensington Market. Housing in Little Italy is a combination of charming older homes, modern townhomes, and stylish lofts for sale. A neighbourhood with one-of-a-kind dining, shopping, and personality? Thats amore!
Welcome to Little Italy
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475 Shaw Street in Toronto: Palmerston-Little Italy House for sale (Toronto C01) : MLS®# C13563358
475 Shaw Street Toronto M6G 3L4 OPEN HOUSE: Jul 18, 202602:00 PM - 04:00 PM EDTOpen House on Saturday, July 18, 2026 2:00PM - 4:00PMOPEN HOUSE: Jul 19, 202602:00 PM - 04:00 PM EDTOpen House on Sunday, July 19, 2026 2:00PM - 4:00PM
$999,999Residential Freehold- Status:
- Active
- MLS® Num:
- C13563358
- Bedrooms:
- 4
- Bathrooms:
- 3
Welcome to 475 Shaw Street, an impressive 2.5-storey semi-detached home situated on a prime 25 x 100-foot lot in Toronto's highly sought-after Palmerston-Little Italy neighborhood. Perfectly combining residential charm with dynamic urban convenience, this versatile 4-bedroom property is move-in ready and stands as a rare opportunity for both growing families and savvy investors. The bright and inviting main level features formal living and dining spaces alongside a spacious eat-in kitchen with excellent potential for owner updates, while the upper level's second kitchen and a separate basement entrance unlock incredible options for extended family living or premium rental income. Outside, the deep backyard serves as a private city oasis ideal for summer BBQs, outdoor dining, and relaxation. Located just a 12-minute walk from Ossington Station and the vibrant Bloor Street corridor, this exceptional home places you steps from trendy cafes, restaurants, beautiful parks, top-tier schools, and all the essential amenities of a truly world-class community. More detailsListed by REALTY ONE GROUP FLAGSHIP- JARROD ARMSTRONG
- RIGHT AT HOME
- 1 (416) 457-1722
- Contact by Email
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452 Montrose Avenue in Toronto: Palmerston-Little Italy House for sale (Toronto C01) : MLS®# C13562684
452 Montrose Avenue Toronto M6G 3H1
$3,299,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13562684
- Bedrooms:
- 6
- Bathrooms:
- 5
A rare opportunity to own an architecturally acclaimed, turnkey income property in the heart of Toronto's coveted Bickford Park/Christie Pits neighbourhood. Delivering a true 3.5%+ cap rate with strong positive monthly cash flow, this exceptional investment offers immediate income with long-term appreciation potential. The property features three separately contained residences: two spacious townhome-style suites plus a newly built, detached laneway house. Designed by Toronto's renowned Fishtnk Design, every detail was thoughtfully considered to maximize tenant appeal while providing low-maintenance, hassle-free ownership. Each suite offers 2 bedrooms, 2 full bathrooms, a private entrance, and its own exclusive courtyard, creating highly desirable living spaces that command premium rents. Bright, open-concept interiors are flooded with natural light and showcase contemporary finishes, efficient layouts, and all-new mechanical systems and infrastructure for worry-free ownership. This award-worthy property has been featured in The Globe and Mail, blogTO, and City Pages, highlighting its exceptional design and innovation. Fully tenanted with excellent occupants, this is a true turnkey investment requiring nothing to do but collect the rent. Located steps from Christie Pits Park, Bickford Park, TTC subway stations, vibrant cafés, restaurants, shops, and some of Toronto's most desirable neighbourhood amenities, this is a premier investment opportunity in one of the city's strongest rental markets. Zoning-compliant, fully-permitted, legal rental suites. New appliances, HVAC, smart thermostats, tankless HWTs, three laundry sets, LEDs, white oak floors, porcelain tile, quartz counters. Separately metered gas and hydro. More detailsListed by EXP REALTY- JARROD ARMSTRONG
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- 1 (416) 457-1722
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427 Crawford Street in Toronto: Palmerston-Little Italy Commercial for sale (Toronto C01) : MLS®# C13559310
427 Crawford Street Toronto M6G 3J7
$3,549,000 /For SaleCommercial- Status:
- Active
- MLS® Num:
- C13559310
- Major Bus.:
- Apts - 6 To 12 Units
- Total Area:
- 0 sq. ft.
A 5.7% cap rate in one of Toronto's most desirable neighborhoods. Legal 6 x 2 bedroom units with incredibly finishes, better than condo quality with more style, grace and personality. Each unit has dishwashers, en-suite laundry, HVAC. The basement is a hidden gem with the potential to add 3 additional apartments. Basement already has rough in's, a must see. 1 min walk to College. Clean Phase 1 2026. Separately metered hydro. Potential for two parking outdoor spaces. Ideally situated near Ossington, Little Italy, Trinity Bellwoods and excellent TTC access, this is a turnkey investment with stable strong in place cash flow with little maintenance required plus potential to add value in the basement. Scheduled Tours of all units will take place Saturday July 18th from 2:00 to 4:00pm. Please confirm attendance. More detailsListed by MYSAK REALTY INC.- JARROD ARMSTRONG
- RIGHT AT HOME
- 1 (416) 457-1722
- Contact by Email
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427 Crawford Street in Toronto: Palmerston-Little Italy House for sale (Toronto C01) : MLS®# C13559278
427 Crawford Street Toronto M6G 3J7
$3,549,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13559278
- Bedrooms:
- 12
- Bathrooms:
- 6
A 5.7% cap rate in one of Toronto's most desirable neighborhoods. Legal 6 x 2 bedroom units with incredibly finishes, better than condo quality with more style, grace and personality. Each unit has dishwashers, en-suite laundry, HVAC. The basement is a hidden gem with the potential to add 3 additional apartments. Basement has rough in's, a must see. 1 min walk to College. Clean Phase 1 2026. Separately metered hydro. Potential for two parking outdoor spaces. Ideally situated near Ossington, Little Italy, Trinity Bellwoods and excellent TTC access, this is a turnkey investment with stable strong in place cash flow with little maintenance required plus potential to add value in the basement. Scheduled Tours of all units will take place Saturday July 18th from 2:00 to 4:00pm. Please confirm attendance. More detailsListed by MYSAK REALTY INC.- JARROD ARMSTRONG
- RIGHT AT HOME
- 1 (416) 457-1722
- Contact by Email
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725 Dovercourt Road in Toronto: Palmerston-Little Italy Commercial for sale (Toronto C01) : MLS®# C13558428
725 Dovercourt Road Toronto M6H 2W7
$1,799,900 /For SaleCommercial- Status:
- Active
- MLS® Num:
- C13558428
- Total Area:
- 2,250 sq. ft.
Discover this professionally maintained mixed-use corner gem at Bloor & Dovercourt, offering both stability and growth potential.The property features one ground-level commercial unit with unbeatable corner exposure and constant foot traffic, along with ample parking options ideal for maximizing visibility and rental income. Main floor leased for 5 years with a +5-year option.Above, the second and third floors are thoughtfully laid out with four rental units, ensuring strong demand in this high-traffic,high-demand location. Situated in the heart of Little Italy, the building benefits from a vibrant neighbourhood known for its charismatic character, lively nightlife, and excellent transit options.This rare opportunity combines location, exposure, and consistent rental appeal, making it a must-have for investors and end users alike. More detailsListed by ROYAL LEPAGE SIGNATURE REALTY- JARROD ARMSTRONG
- RIGHT AT HOME
- 1 (416) 457-1722
- Contact by Email
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725 Dovercourt Road in Toronto: Palmerston-Little Italy House for sale (Toronto C01) : MLS®# C13558394
725 Dovercourt Road Toronto M6H 2W7
$1,799,900Residential Freehold- Status:
- Active
- MLS® Num:
- C13558394
- Bedrooms:
- 4
- Bathrooms:
- 2
Discover this professionally maintained mixed-use corner gem at Bloor & Dovercourt, offering both stability and growth potential.The property features one ground-level commercial unit with unbeatable corner exposure and constant foot traffic, with lots of parking options, ideal for maximizing visibility and rental income. The Main floor is leased for 5years with an option +5 Years.Above, the second and third floors are thoughtfully laid out with four rental units, ensuring strong demand in this high-traffic,high-demand location. Situated in the heart of Little Italy, the building benefits from a vibrant neighbourhood known for its charismatic character, lively nightlife, and excellent transit options.This rare opportunity combines location, exposure, and consistent rental appeal, making it a must-have for investors and end users alike. More detailsListed by ROYAL LEPAGE SIGNATURE REALTY- JARROD ARMSTRONG
- RIGHT AT HOME
- 1 (416) 457-1722
- Contact by Email
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493 Ossington Avenue in Toronto: Palmerston-Little Italy House for sale (Toronto C01) : MLS®# C13545500
493 Ossington Avenue Toronto M6G 3T3
$999,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13545500
- Bedrooms:
- 7
- Bathrooms:
- 2
Welcome to 493 Ossington Avenue-an exceptional opportunity to own a legal duplex in the heart of the highly sought-after Palmerston-Little Italy neighbourhood. Built in 1896, this grand residence blends timeless character with modern upgrades, offering over 4 levels of versatile living space ideal for multi-generational families or buyers seeking a strong mortgage helper. With five bedrooms, including two on the finished third level, and soaring ceilings on the main floor, the home delivers the space and flexibility today's buyers crave.Thoughtfully updated and move-in ready, the property offers multiple living configurations. Enjoy it as a spacious single-family home, or take advantage of the legal duplex setup by living in one unit while renting the other. The upper level functions beautifully as a large 3-bedroom suite, creating excellent income potential without compromising comfort or privacy. A rear addition expands the main floor with a generous family room, while the separate living and dining areas offer the option to open up into one expansive entertaining space. Outside, a rare double-car garage with laneway access provides easy, secure parking-an incredible asset in this location. With a 95 Walk Score, 93 Transit Score, and 76 Bike Score, everything you need is at your doorstep. Walk to the vibrant energy of College Street and Little Italy, explore Kensington Market, enjoy nearby green spaces like Dufferin Grove Park and Trinity Bellwoods, and benefit from close proximity to Toronto Western Hospital.This is more than just a home-it's a flexible investment in lifestyle and long-term value. Whether you're accommodating extended family, offsetting your mortgage with rental income, or simply looking for space in one of Toronto's most dynamic communities, 493 Ossington delivers a rare and compelling opportunity. More detailsListed by ROYAL LEPAGE SIGNATURE SUSAN GUCCI REALTY- JARROD ARMSTRONG
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- 1 (416) 457-1722
- Contact by Email
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599 Bloor Street W in Toronto: Palmerston-Little Italy Commercial for sale (Toronto C01) : MLS®# C13543976
599 Bloor Street W Toronto M6G 1K5
$129,000 /For SaleCommercial- Status:
- Active
- MLS® Num:
- C13543976
- Major Bus.:
- Restaurant
- Total Area:
- 780 sq. ft.
An exceptional retail opportunity at Bloor & Bathurst, in the heart of Koreatown, one of downtown Toronto's busiest and most sought-after commercial corridors. Located within a newly constructed condominium just minutes from the University of Toronto, this space enjoys steady foot traffic and a built-in customer base from the residents above. Equipped with a fully functional commercial kitchen and a liquor license, the unit is move-in ready for a restaurant, café, bar, or any food-related concept. Its manageable footprint maximizes operational efficiency while keeping overhead costs low. A rare opportunity to establish your business in a proven, high-visibility downtown location. More detailsListed by REMAX YC REALTY- JARROD ARMSTRONG
- RIGHT AT HOME
- 1 (416) 457-1722
- Contact by Email
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308 Roxton Road in Toronto: Palmerston-Little Italy House for sale (Toronto C01) : MLS®# C13542230
308 Roxton Road Toronto M6G 3P9
$1,100,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13542230
- Bedrooms:
- 3
- Bathrooms:
- 2
A rare opportunity in one of Toronto's most sought-after neighbourhoods. Offered for the first time in nearly 80 years, 308 Roxton Road is ready to be reimagined-a classic Toronto home in the heart of Palmerston-Little Italy with extraordinary potential.This three-bedroom, two-bathroom semi-detached home is ideally suited to builders, renovators, and investors alike. Whether your vision is a thoughtful restoration, a complete renovation, or unlocking its investment potential, this classic Victorian home offers an outstanding opportunity.Offering approximately 1,416 square feet above grade on a deep 17.5 x 126-foot lot, the property enjoys an outstanding location just north of College Street and east of Ossington Avenue. The generous lot depth and rear laneway access offer exciting potential for a future two-car garage and laneway suite, subject to buyer verification of all applicable City of Toronto approvals, permits, zoning requirements, and due diligence.Enjoy everything Palmerston-Little Italy has to offer, with vibrant cafés, restaurants, shops, TTC, parks, schools, and bike routes just steps from your door. Surrounded by beautifully restored homes, 308 Roxton Road is ideally positioned in a neighbourhood where thoughtful renovations continue to enhance both character and value.Opportunities combining a prime location, generous lot, and laneway access rarely come to market. Bring your contractor, your architect, and your vision to unlock everything this remarkable property has to offer. More detailsListed by RE/MAX ROUGE RIVER REALTY LTD.- JARROD ARMSTRONG
- RIGHT AT HOME
- 1 (416) 457-1722
- Contact by Email
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539 Crawford Street in Toronto: Palmerston-Little Italy House for sale (Toronto C01) : MLS®# C13534424
539 Crawford Street Toronto M6G 3J9
$3,960,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13534424
- Bedrooms:
- 4
- Bathrooms:
- 5
Welcome to this Jewel Box nested in the heart of Little Italy. This French town house-inspired home is filled with luxury details in every corner. With more than 3,500 sq ft of finished living space and soaring ceilings on each level, this home is the destination of your search in downtown Toronto. From intricate scroll-style moldings, custom marble fireplaces, to floating staircases, there's no shortage of elegance and sophistication encapsulated in this labor of love. 3rd level's open concept suite with large rear terraces offers unobstructed city views and the CN Tower. ** EXTRAS ** Please see feature sheets for full home details. Builder offers Tarion new home equivalent warranty. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- JARROD ARMSTRONG
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- 1 (416) 457-1722
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730 Shaw Street in Toronto: Palmerston-Little Italy House for sale (Toronto C01) : MLS®# C13488148
730 Shaw Street Toronto M6G 3L7
$2,599,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13488148
- Bedrooms:
- 5
- Bathrooms:
- 4
Exceptional Luxury Fourplex in the Heart of Palmerston-Little Italy, Toronto Premier Location, High-Quality Construction, Turnkey Investment Bright, beautiful, high-end fourplex in prestigious Palmerston-Little Italy - one of Toronto's most vibrant and in-demand communities! This exceptionally well-built fourplex offers four luxury self-contained apartments with high-end finishes and fixtures, hardwood flooring, full custom kitchens with large islands, granite countertops, full-size stainless steel appliances, in-suite laundries, and independent heating and air conditioning systems. Lower level with heated floor system as well. Spacious, thoughtfully designed layouts. Lots of natural light, high ceilings, large balconies and private entrances. Top-quality construction built with long-term performance and style in mind. Each unit has separately metered gas and hydro and rough-in for water metering. On-site parking and backyard. Steps to TTC Bloor subway line and buses, Bloor St, Harbord St., College St, Annex, Little Italy, Ossington Strip, restaurants, shops, schools, parks, bike paths and all amenities. Minutes to U. of T. , University Health Network, Yorkville, and Downtown Core.Ideal for investors or multi-generational living. A turnkey investment in one of Toronto's most coveted neighbourhoods! More detailsListed by RIGHT AT HOME REALTY- JARROD ARMSTRONG
- RIGHT AT HOME
- 1 (416) 457-1722
- Contact by Email
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458 Markham Street in Toronto: Palmerston-Little Italy Commercial for sale (Toronto C01) : MLS®# C13482698
458 Markham Street Toronto M6G 2L2
$3,400,000 /For SaleCommercial- Status:
- Active
- MLS® Num:
- C13482698
- Major Bus.:
- Other
- Total Area:
- 4,427 sq. ft.
Professionals or Investors. Main floor DENTAL OFFICE plus 4 residential units. This grand beauty has been very well maintained and it represents a time of design and construction not seen in generations. There are currently 4 units plus an unoccupied professional dental office which has an entrance on Harbord Street with great exposure and is approximately 1,400 sq. ft. . Located in the heart of the Annex, you are right along Harbord Street at Markham and only steps to Bathurst, Bloor street nd the subway. This is a perfect live/work space or investment opportunity. Over 4,200 square feet, the building was extensively renovated in 1990 and the roof was fully replaced 2 years ago. There is parking at the rear with easy access off Harbord St. This bustling neighborhood attracts people who want a beautiful downtown area with character, architecturally beautiful homes from the early 1900's and super convenient access to downtown, U of T and hospital row. Currently there are 2-two bedroom units, 1-one bedroom unit and a bachelor unit. Three of the units have their own balconies. The basement is a high and very dry basement with a separate entrance, storage and a laundry area for the dental clinic. Plans currently exist to convert the dental office into 2 more residential units. More detailsListed by RE/MAX HALLMARK REALTY LTD.- JARROD ARMSTRONG
- RIGHT AT HOME
- 1 (416) 457-1722
- Contact by Email
Data was last updated July 18, 2026 at 06:15 AM (UTC)
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