Ossington & College Real Estate for Sale

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.

Welcome to 308 Roxton Road, an exceptional opportunity to reimagine a home in the heart of Palmerston Little Italy, one of Toronto's most sought after downtown neighbourhoods. Ideally located just north of College Street and east of Ossington Avenue, this three bedroom, two bathroom semi detached home sits on a generous 17.5 by 126 foot lot and offers 1,416 square feet of above grade living space. Whether you are planning a complete renovation, restoring the home's original character, or designing a modern custom residence, this property offers incredible potential in a location where renovated homes are highly sought after. The deep lot may also provide opportunities to expand the existing home and could offer future laneway suite potential, subject to all required City of Toronto approvals and zoning requirements. Step outside and experience the best of downtown Toronto. Enjoy the renowned restaurants, cafés, bakeries, boutiques, and vibrant atmosphere of College Street and Ossington Avenue, with nearby parks, schools, TTC access, and cycling routes all within easy reach. This walkable neighbourhood combines historic charm with an unbeatable urban lifestyle, making it a favourite among families, professionals, and investors alike. Opportunities like this are increasingly rare. Whether you are searching for your forever home, a renovation project, or a long term investment in one of Toronto's most desirable neighbourhoods, 308 Roxton Road is ready for your vision.

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.

Welcome to 204 Grace Street, a beautifully renovated home where timeless character meets modern sophistication in the heart of Trinity Bellwoods. Thoughtfully designed across three finished levels, this exceptional residence features soaring high ceilings, oak hardwood flooring, exposed brick accents, custom millwork, designer lighting, and premium finishes throughout. The main level offers elegant principal rooms and a stunning chef's kitchen with quartzite natural stone countertops and backsplash, an eight-foot island, and premium Café appliances. Upstairs, two spacious bedrooms, a stylish five-piece family bath, upper-level laundry, and a custom walk-in closet/home office provide exceptional functionality. The third floor primary retreat features a luxurious five-piece ensuite and custom closet storage. Major upgrades include 200-amp electrical service, new windows and doors throughout, and a Tesla EV charger with dedicated subpanel in the detached garage, perfectly equipped for modern living. Professionally landscaped grounds and new interlock stonework complete this truly turnkey offering. The self-contained lower level one bedroom apartment offers a fantastic opportunity for additional rental income. Ideally located steps to Trinity Bellwoods Park, Ossington, and College Street, and surrounded by the very best of Little Italy and Trinity Bellwoods, from beloved restaurants and independent cafés to boutique shops and vibrant weekend markets. This is Toronto neighbourhood living at its finest.

Welcome to this brand new, never-lived-in luxury residence at Concord Canada House, one of downtown Toronto's most prestigious landmark developments, ideally located steps from the CN Tower, Rogers Centre, Union Station, and the waterfront.Perched on a high floor, this exceptional 3-bedroom, 2-bathroom suite offers approximately 1,128 sq.ft. of thoughtfully designed interior space along with an expansive 277 sq.ft. heated terrace for year-round enjoyment. Enjoy breathtaking, unobstructed east-facing panoramic views of Toronto's iconic skyline and Lake Ontario through dramatic floor-to-ceiling windows that flood the home with natural light.Designed with sophistication and functionality in mind, the suite features premium Miele appliances, sleek contemporary finishes, and innovative four-season balcony doors that seamlessly extend the living space outdoors. From your private terrace, enjoy spectacular skyline views and even catch live events at Rogers Centre during the summer months.Residents enjoy access to world-class amenities including the iconic 82nd-floor Sky Lounge and Sky Gym, indoor swimming pool, ice-skating rink, touchless car wash, 24-hour concierge, and more.Located in the heart of downtown Toronto, moments from Scotiabank Arena, the Financial District, King West, fine dining, luxury shopping, and endless entertainment, this residence offers an exceptional blend of luxury, lifestyle, and convenience.Now offered below the original 2019 purchase price, this is a rare opportunity to secure outstanding value in one of Toronto's most sought-after luxury developments. Includes one parking space and one locker.

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.

*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.

Some properties come to market once a decade. This one comes along once in a generation. 29 Shannon Street has been owned by the same family since 1967 and is hitting the market for the first time in nearly 60 years. A rare legal duplex on a 40 x 118 ft lot in the heart of Trinity Bellwoods, move-in ready as configured, fully livable, and with serious income generating potential. Purpose built for multigenerational living, the upper unit spans the second and third floors with six bedrooms, generous living space and kitchen, and the bathroom has a classic clawfoot tub and shower. The main floor operates as a fully self-contained suite with a full kitchen, pantry, large living and dining rooms, two bedrooms, and a beautifully renovated bathroom with walk-in shower. Both basements are large and offer significant square footage with value-add potential and private storage for each unit. Walk outside to a generous yard, patio, detached shed with garden suite potential, and private drive with parking for approximately seven vehicles. Five minutes to Trinity Bellwoods Park, steps to Ossington, Queen West, top-rated schools, and TTC. Committee of Adjustments approved plans are already in place and they are extraordinary. The third floor transforms into a private primary retreat with a full ensuite, dedicated living area, and a large balcony with 180 degree Toronto skyline views. The main floor opens dramatically with a 20 foot double vaulted living space, a French country inspired kitchen, a fireplace as the centrepiece, and rear sight lines that pull natural light deep into the home. The heritage facade stays. Everything behind it transforms. The approved lower level introduces a 9 foot walkout suite with direct backyard access, purpose built as an in-law suite or nanny quarters. No approvals to chase. No uncertainty. The vision is already permitted. All that remains is the build.

Let's be honest. Vacant rarely looks this good. Two recently severed lots. Side by side. 25x109 feet each (353 & 359 Crawford). Fifty feet of combined frontage sitting right in the heart of Trinity Bellwoods, tucked neatly between College & Dundas on the west side of Crawford. Let that land for a second. This isn't a renovation play dressed up as something bigger. This is something bigger. We're talking 7,300+ square feet of interior space spread across a 2.5-storey brick building. The kind of early-20th-century hybrid that borrows from late Edwardian bones and the Craftsman sensibility without apologizing for it one bit. Huge street presence. Very Toronto. Exceptionally rare. The property arrives vacant. No tenants, no complications, no inherited headaches. Just a blank slate with serious bones and even more serious upside. A commanding front porch sets the tone, a rear extension adds depth and when you make your way to the second or third floor at the back? Unobstructed CN Tower views. Rear laneway access serves both lots. Two-car parking per property. And upside potential that your spreadsheets will absolutely love. No encroachments, no heritage restrictions, no drama. A survey is available and ready to go. For the builders, architects, infillers, and visionaries who've been waiting for the right opportunity in the right neighbourhood. This is the call. The approvals conversation starts here, and the numbers make sense on both sides of the table. Cont...

In the Heart of Toronto's Vibrant Little Italy, this Exceptional Triplex at 216 Montrose Avenue offers a Rare Opportunity for Investors, End-Users, or Multi-generational living. Featuring Sun-Filled, self-contained Suites. The Home Includes 3 Toronto Hydro meters and 3 Enbridge Gas meters for added Convenience and Flexibility. Freshly painted throughout, each unit Feels Bright, Clean, and Inviting. The home also Features a Rear Basement Entrance for easy access and functionality. Step outside to a Breathtaking Private Backyard Oasis, complete with a Separate Garage opening onto the coveted Galipo Brothers laneway, with Convenient Access from both Crawford Street and Montrose Avenue. Perfect for Summer Entertaining or Quiet Outdoor Enjoyment.Ideally located just Steps from the Endless Shops, Cafés, Restaurants, Grocery Stores, and Lively Entertainment along College Street, with TTC streetcar access right at your Doorstep.

Fully renovated Multiplex in a prime, high-demand downtown location, offering a rare turnkey investment opportunity with strong income potential. This exceptional property comprises four self-contained units: Units 1 & 2 & 3 each feature 4 spacious bedrooms and 2 full bathrooms, while the lower-level unit offers a well-designed 3-bedroom, 2-bathroom layout. All units have been extensively upgraded with modern, high-quality finishes, including new flooring, contemporary kitchens with stainless steel appliances, and elegantly renovated bathrooms. Each suite is equipped with its own private in-suite laundry, enhancing tenant convenience and desirability. Bright, functional layouts with generous principal rooms and large windows provide abundant natural light throughout. A newly constructed rear fire escape staircase has also been added to enhance safety and meet current building standards. The property includes a highly sought-after detached 4-car garage at the rear, offering valuable parking in this dense urban setting. Additional features include a rooftop sun deck with seasonal CN Tower views, adding further appeal for tenants. Ideally situated in one of Toronto's most desirable downtown neighborhoods, just steps to U of T, College Street, Metro grocery, cafés, restaurants, parks (Trinity Bellwoods, Bickford), YMCA, and the Bob Abate Community Centre. A truly turnkey, low-maintenance asset in an unbeatable location.

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.

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.

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.

Welcome to 358 Roxton Road, a charming home in the heart of Toronto's vibrant Palmerston-Little Italy neighbourhood. Set on a beautiful corner lot, this property offers a rare blend of character, space, and versatility. Featuring three spacious bedrooms, two bathrooms, and two additional office spaces on the main and second floors, the home showcases original character throughout, with generous room sizes and timeless details. The finished basement adds excellent value with a separate entrance, full kitchen, bathroom, and living area, ideal for a potential in-law suite or rental opportunity. A detached garage provides added convenience while also presenting the opportunity to build a two-storey garden suite - a compelling option for additional income and long-term value (see report). Sitting on a corner lot, allows for enhanced curb appeal and outdoor space. Located steps to great schools, transit, and the lively shops, cafés, and restaurants along College Street, and within walking distance to the Bloor subway line, this sought-after neighbourhood is known for its tree-lined streets, strong community feel, and vibrant urban lifestyle. Updated electrical wiring and 100amp panel completed in 2007.

Don't miss this tastefully updated 2.5-storey property in one of Toronto's most sought-after neighbourhoods. An excellent opportunity for investors, this turnkey income-generating home features three well-maintained units, each offering modern finishes and strong rental appeal. Upper Unit (2nd & 3rd Floors): A spacious 3-bedroom, 1-bathroom suite showcasing updated flooring, durable laminate throughout, and a ductless A/C system for year-round comfort. Main Floor Unit: Bright and inviting, this open-concept space features a generous eat-in kitchen, an updated bathroom, ductless A/C and direct access to a private backyard.Basement Unit: A self-contained 1-bedroom suite complete with ceramic flooring, ductless A/C, and a separate front entrance-ideal for added income or extended family. HWT (2026). Garage & Laneway Access: A detached garage at the rear offers valuable laneway access, presenting additional income potential or flexible personal use.Fully tenanted with excellent AAA+ occupants who must be assumed. A rare opportunity to secure a solid, income-producing asset in a high-demand location-act quickly!

REDUCED TO BE SOLD! Bring all offers! Vacant possession. Legal triplex + Large Laneway house potential. Solid brick large 3-floor home. Semi-detached. Large 3 floor home + basement apartment with separate entrance outside stairs down. Wide 20.5' X 125 foot lot. 5 bedrooms. Large 2 car concrete block garage (detached!). Prime Little Italy street steps to College St and Metro grocery. 3 separate entrances. Great neighbours. Very Quiet one-way street. Montrose Jr. Public School and Art Eggleton Park at end of the street! Approx. 2927 sq. ft. finished according to Floor Plans. 2 hydro meters. See Floor plans.