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$2,049,000
7 Beds ⋅ 5 Baths ⋅ C13604612 MLS
A well-maintained detached fourplex in the heart of one of Toronto's most sought-after neighbourhoods, Palmerston Little Italy. This versatile property offers four self-contained units ideal for investors, co-ownership partners, or multi-generational living. The spacious main-floor 3-bed, 2-bath suite features ensuite laundry and direct access to a beautifully finished backyard with built-in seating and decking. The second level offers two bright 1-bedroom suites, each with private balconies, while the expansive lower level hosts a 2-bedroom suite spanning the full footprint of the home. All tenants month-to-month. The detached 2-car garage and laneway potential offer even more opportunity for future value. Perfectly situated steps to Harbord, Ossington, College, and Bloor - enjoy proximity to Little Italy, U of T, TTC, and all the amenities of downtown living. A rare opportunity to generate income, share ownership, or live together while maintaining independence.

396 Roxton Road, Toronto
$2,580,000
6 Beds ⋅ 5 Baths ⋅ C13580032 MLS
Welcome to this true architectural nested in the Toronto heart Little Italy. A family home w/nearly 3000 sq. ft. of living space on 4 levels. The open concept Main floor comes with a custom chief kitchen, with beautiful central island and B/I appliances. Main floor also offers all functional area, your in-home office, powder room, laundry site, mud area. Upstairs offers 4 well design bedrooms, which have 3 en-suites. The Primary Bedroom land on 2nd floor have a beautiful 4PC en-suites, showroom W/I closet and picture window to your lovely back yard. The Primary Bedroom land on 3rd floor have the most functional layout in downtown Toronto. 5PC En-suites, W/I closet, Floor to Ceiling Sliding Doors walk to your private Balcony with a CN-Tower view. Your basement comes with 2nd kitchen, 2nd laundry and other two rooms. You can use basement as your entertainment area, which one room be your gym and other room be your guest bedroom. Or, if needed, this is a legal 2 bedroom basement apartment with separate W/O entrance. Then, we walk into your quite back yard, the huge deck comes with BBQ gas supply, the little Green Area design for your pets and a Double Car laneway garage with separate electric panel supply a Tesla Universal Wall Connector Hardwired Electric Vehicle (EV) Charger.

431 Roxton Road, Toronto
$1,799,900
4 Beds ⋅ 2 Baths ⋅ C13558394 MLS
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.

725 Dovercourt Road, Toronto
$999,000
7 Beds ⋅ 2 Baths ⋅ C13545500 MLS
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.

493 Ossington Avenue, Toronto
$1,100,000
3 Beds ⋅ 2 Baths ⋅ C13542230 MLS
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.

308 Roxton Road, Toronto
$3,400,000
5 Beds ⋅ 6 Baths ⋅ C13479674 MLS
Professionals or Investors, 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 neighbourhood 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 seperate entrance, storage and a laundry area for the dental clinic. Plans currently exist to convert the dental office into 2 more residential units.

458 Markham Street, Toronto
$1,838,000
7 Beds ⋅ 4 Baths ⋅ C13460440 MLS
Prime Palmerston - Little Italy opportunity! Situated on a coveted tree-lined street in one of Toronto's most desirable central neighborhoods, this property offers flexibility and future potential. Currently used as a multi-unit residence, the large building envelope presents an outstanding opportunity for investors seeking income potential or discerning buyers looking to transform the existing structure into a sophisticated designer executive family home. Surrounded by beautiful renovated properties and just steps to the vibrant energy of College Street's renowned restaurants, cafes, boutiques, parks and transit, the location is second to none. A rare chance to secure a property in a neighbourhood where lifestyle, character and long-term value converge. Tenants are month-to-month. Make income while you design or request vacant possession.

464 Euclid Avenue, Toronto
$2,799,000
7 Beds ⋅ 6 Baths ⋅ C13458850 MLS
A smart, stylish investment in the heart of Little Italy. This fully rebuilt home offers nearly 3,800 total sq ft including basement of luxury living across 3 finished units with separate entrances, hydro, HVAC, laundry, and kitchens. High-end finishes, custom millwork, Sub-Zero/Wolf appliances, and spa-like baths add turnkey appeal. Ideal for portfolio investors, multi-generation or live-in owners - occupy one unit and let the others cash flow. Steps to Bloor, TTC, U of T, and Ossington's best restaurants. Truly one of Toronto's most thoughtful multi-unit redevelopments.

734 Shaw Street, Toronto
$1,788,000
5 Beds ⋅ 4 Baths ⋅ C13441718 MLS
Exceptional Income-Generating Victorian in the Heart of Little Italy. A rare opportunity to own a stunning, stylishly renovated Victorian in one of Toronto's most coveted neighborhoods. Currently tenanted, live in one apartment and rent the other two or leave fully tenanted. This versatile property offers incredible investment potential, seamless multi-unit living, or an easy conversion back to a single-family residence with a basement apartment. Step inside to discover three modern loft-style apartments-each uniquely designed with exposed brick walls, teak flooring, vaulted ceilings, skylights, and sleek contemporary kitchens and bathrooms featuring concrete countertops and clean modern finishes. Solid hardwood floors flow throughout most of the home, highlighting its character and craftsmanship. The top unit, fully renovated to the studs in 2021, shows beautifully and is a standout feature. A separate entrance to the basement allows for an additional suite, perfect for income or in-law accommodations. Outdoor living is a dream with three private decks, a beautifully landscaped front and backyard, and a lush private garden-a peaceful retreat in the middle of the city. The solid block detached garage is highly coveted in this neighborhood. With an updated furnace, quality renovations, and unbeatable location, this home is the perfect blend of charm, style, and smart investment. Steps to transit, cafes, restaurants, parks, and all the vibrant amenities of Little Italy. A truly phenomenal property offering unmatched flexibility, strong income potential, and timeless Victorian character.

410 Manning Avenue, Toronto
$1,949,900
4 Beds ⋅ 3 Baths ⋅ C13415878 MLS
*LEGAL DUPLEX WITH SEPARATE ENTRANCE TO UNDERPINNED BASEMENT UNIT. * EXCELLENT INVESTMENT! GROSS CAP RATE APPROX 5%. DOUBLE DET. GARAGE SERVICED BY LANE WAY,***MAY HAVE OPPORTUNITY FOR LANE WAY HOUSING***. BASEMENT APARTMENT: NEWLY UNDERPINNED AND RENOVATED APPROX 6 YRS OLD. *MAIN FLOOR UNIT: NEW FLOORING (2026) AND WASHROOM (2026). UPPER LEVEL UNIT: (2nd & 3rd FLR) WITH 2 WALK-OUTS (RENO APPROX 6 YEARS AGO). 5 ROOMS. CAN BE USED AS A 2 OR 3 BEDROOM UNIT . BUYER TO ASSUME TENANTS.

225 GRACE Street, Toronto
$5,749,900
6 Beds ⋅ 7 Baths ⋅ C13225554 MLS
Palmerston Boulevard is one of the city's most storied streets. Gated at the entrance, lined with historic cast-iron lampposts, and canopied by mature trees that have watched this neighbourhood evolve for over a century. There is simply no other street like it in Toronto. Little Italy at your doorstep. Restaurants, cafés, culture, and the subway are all within reach - yet the moment you turn onto Palmerston, the city softens. Equally rare as the location is the expansive 50 by 127 foot lot with a private drive, lane access, and the potential to build a two-storey laneway home with an integrated two-car garage. Options like this don't surface often. Step through the pillared front porch into three self-contained units, each with its own distinct character. From traditional to contemporary. Keep it as the turnkey multi-unit property it already is - an intelligent hold in one of Toronto's most enduring neighbourhoods - or reimagine it entirely as a singular grand residence. For those with the vision to create their dream home, few canvases in this city are more compelling. Some addresses find you. This one was waiting for you all along.

386 Palmerston Boulevard, Toronto
$1,174,900
4 Beds ⋅ 2 Baths ⋅ C13154056 MLS
Welcome to 667 Ossington Avenue, a spacious and charming 2.5-storey semi-detached home in the heart of Toronto. Featuring 4 generously sized bedrooms, this residence offers the perfect blend of comfort, functionality, and urban convenience-ideal for growing families or savvy investors. The main floor boasts a bright and inviting layout with a formal living room and dining room, perfect for both everyday living and entertaining. The eat-in kitchen provides ample space for family meals and gatherings, with great potential to customize to your taste. A second kitchen on the upper level adds exceptional convenience and offers excellent potential for extended family living or rental income. Step outside to a generously sized backyard offering plenty of room to host family and friends for summer BBQs, outdoor dining, and relaxing evenings-your own private outdoor retreat in the city. Situated just steps from Ossington Station and the vibrant Bloor Street corridor, you'll enjoy easy access to transit, trendy shops, cafes, and restaurants. This prime location also offers walking distance to excellent schools, parks, and all essential amenities. A rare opportunity to own a well-located home in one of Toronto's most sought-after neighborhoods.

667 Ossington Avenue, Toronto
$1,849,000
6 Beds ⋅ 3 Baths ⋅ C13150550 MLS
Welcome to 404 Manning Ave - a rare opportunity to own a beautifully maintained 2-storey semi-detached Income Property featuring three separate self-contained apartments on a prime 25 x 130 foot lot. Offering 6 bedrooms, 3 kitchens, and 3 bathrooms, this versatile property is ideal for investors, multi-generational families, or buyers seeking a live-in income opportunity with exceptional flexibility and long-term potential. A triple-car garage with laneway access provides the exciting possibility to build a 2-storey garden suite, creating additional living space or future rental income potential. Situated on a coveted tree-lined street in one of downtown Toronto's most desirable neighborhoods, this home is perfectly positioned in the Trinity-Bellwoods/Palmerston-Little Italy area. Just steps from College Street, the location offers outstanding walkability and easy access to Dundas Street West, Queen West, public transit, streetcars, and subway connections. This vibrant community blends quiet residential charm with dynamic urban living, surrounded by boutique shopping, acclaimed restaurants, cafés, and cultural destinations including Kensington Market and Trinity Bellwoods Park. Walking distance to University of Toronto , Toronto Western Hospital and all amenities.

404 Manning Avenue, Toronto
$1,299,999
4 Beds ⋅ 2 Baths ⋅ C13131154 MLS
Welcome to 623 Ossington Ave, a rarely offered detached Located in the heart of Palmerston-Little Italy, one of Toronto's most desirable neighbourhoods. This detached home on a wide lot is a Renovator's dream as it presents limitless opportunities. Either renovate your dream home or renovate as an investment property. The detached lot allows for tear down and rebuild opportunities as well. The long lot allows for building of a sizable laneway house and still provides ample backyard space. Laneway Housing Advisors confirmed the property is eligible for building a 1,312 square feet laneway house over 2 floors. A++ location minutes away from Ossington Subway, restaurants, cafes, shops along Bloor, Harbord and College Streets. Family oriented neighbourhood with great schools. This home is well maintained and being offered for the first time in over 30 years. Your next home is here!

623 Ossington Avenue, Toronto
$1,868,000
6 Beds ⋅ 3 Baths ⋅ C13107898 MLS
Detached Double Car Garage The Must See beauty *Absolutely Stunning *Fantastic Location *Deep and Wide Lot(25*125) *Newer Double Garage door, *Fantastic Open Concept Great For Entertaining *Smooth Ceilings *Pot Lights *Ceramic Tiles/Hardwood Through out *Gourmet Chefs Kit W/Backsplash/Stnls Stl Appl/Centre Island*California Shutters *9Ft Ceilings On Main Floor *Owned Hot water Tank, Newer Furnace, Newer Ac(2025) *Finished 3 Bedrooms Basement W/Walk-Up, the den on the First floor can be convert to 4th bed, professional front and back Yard *Steps To Kensington Market/U Of T/Bike Path/Transit*Worth Every Penny*10++*

231 Clinton Street, Toronto
$1,899,000
10 Beds ⋅ 5 Baths ⋅ C13057358 MLS
Fantastic income opportunity for investors, contractors or renovators seeking a revenue generating property. Located on a massive 30 x 133 ft lot, offering over 3,000 sq. ft. of living space. Features include an expansive driveway with parking for 4 cars, plus a single car garage and shed. A laneway runs beside and behind the property, providing additional development potential. The property features high ceilings throughout and shared laundry in the basement. Each unit has a kitchen and 4 piece bathroom. Main floor boasts high ceilings, stained glass, and walkout to back deck, Vintage crown molding, and original hardwood. Large living room with fireplace, large master bedroom, 2 additional bedrooms, and spacious eat-in kitchen. second floor features a walkout to balcony from living room. third floor features amazing views of the Toronto skyline, walkout from the family room to the third floor balcony. Basement features a cellar and walkout to the backyard. Located in a highly desirable, family-friendly neighbourhood in the heart of Little Italy, steps to the TTC, schools, restaurants, and shops.

237 Roxton Road, Toronto
$1,849,000
3 Beds ⋅ 2 Baths ⋅ C13056172 MLS
Welcome to this solid detached 3-bedroom home located in one of the city's most trendy and desirable neighbourhoods, close to excellent schools, steps to College street & Ossington, ideally close to vibrant restaurants, cafés, parks, and local conveniences. This solid home offers a fantastic opportunity for buyers to modernize and customize to their own style and personal taste. Comfortable & well maintained, you can move in now & update over time at your pace. Enjoy a spacious private backyard, ideal for family gatherings or summer entertaining, plus a solid block garage and convenient two-car parking. The garage also presents potential for future laneway housing, similar to what other neighbours on the street have created (subject to city approvals). The walkout basement adds incredible value with excellent potential for an in-law suite or rental income opportunity. (subject to city approvals) An exceptional chance to invest, customize, and create a beautiful home in a prime location.

382 Roxton Road, Toronto
$1,589,990
5 Beds ⋅ 3 Baths ⋅ C12979318 MLS
Welcome To 543 Crawford St, A Rare Detached Brick Home In The Heart Of Little Italy. Spacious 4+1 Bedrooms, Even Showcases A Charming CN Tower View. Functional Layout And Multiple Entrances Offering Endless Possibilities. Enjoy A Bright Main Floor with 9 Ft Ceilings, Walkout To A Private Backyard And Rare 2-Car Garage. Lower Level Features Separate Front & Rear Entrances. Perfect For Income Potential. Located On One Of The Most Sought-After Streets, Just Steps To College St, Restaurants, Shops, Parks & TTC. This Is A Fantastic Opportunity To Own A True Family Home In One Of Torontos Most Vibrant And Desirable Neighbourhoods.

543 Crawford Street, Toronto
$1,495,000
6 Beds ⋅ 2 Baths ⋅ C12611292 MLS
Home with Two Apt Units: Apt 2 Second/Third Floor renovations have finally been completed (4 months long). Now, rented on a lease for $3,600/month plus hydro. Tens of thousands of dollars have been spent upgrading this apartment. Apt 1: Tenants on Month-to-Month, former Owners' apt, open-concept main-floor, renovated kitchen with stainless steel appliances, marble counter and many other upgrades. Can be used as a 2 or 3-Bdrm apartment. Apt 2: is a 3-bedroom apt. Mechanically sound home, but we will let your Home inspector verify this. Possibilities abound: live in one unit and use the $3,600/month to help pay the mortgage, or assume both Tenants, or maybe in the future you want to convert back to a very large single-family home with still a potential basement ensuite. Parking from the laneway, 2 spots depending on vehicle size. This home is very close to the Ossington Subway station and multiple transit options. Fenced-in backyard with a shed included. This owner has pride of ownership and has made multiple renovations over the years. Since 2022, to name a few, new electrical completed with permits, new furnace, new central air conditioning, hot water tank owned, new electrical panel, new flooring, new drywall and plaster walls and ceilings, new paint, new drains and basement flooring, new full-sized stainless steel refrigerator, new stainless steel induction stove and oven on the second floor. A complete renovation of the main floor and basement some years ago. As per Apt 1 tenant's request and respect for tenant's privacy, no interior photos are posted. Showings are available by appointment with appropriate notice. The seller is confident about the property and its condition; there might be a possible discussion for some Seller-assisted financing.

257 Concord Avenue, Toronto