A rare detached freehold opportunity in the heart of Little Italy-one of Toronto's most iconic and tightly held neighbourhoods. Homes on their own lots in this part of the city are increasingly difficult to secure, and truly detached freeholds represent less than 1% of the downtown housing supply. Opportunities like this remain exceptionally limited and carry enduring long-term value. Built in 1905, this home offers historic charm and architectural character that simply cannot be replicated today. Its solid structure and attractive lot provide a strong foundation for those planning future renovations or a complete redesign. The flexible layout includes multiple living areas, three bathrooms, and a full basement with its own entrance-ideal for multi-generational living, work-from-home setups, long-term investment, or modernization. A freehold for the cost of a larger condo. For the price of a typical downtown unit-without monthly maintenance fees, shared decision-making, or restrictions from a condo board-you can own a detached freehold with land, privacy, and complete control over how the property evolves. It's a level of autonomy and long-term value that condominium ownership simply cannot match. Crawford Street is lined with character homes, mature trees, and long-standing local businesses that form the cultural fabric of Little Italy. With exceptional walkability, transit access, parks, restaurants, and everyday conveniences, it's a community where families often remain for generations. Homes here rarely turn over, further underscoring the scarcity and desirability of this offering. A unique opportunity to secure land in a centrally located, culturally rich, and consistently in-demand downtown neighbourhood. Property is being sold as-is, where-is, with no further work to be completed by the sellers.

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415 Crawford St, Toronto, Ontario M6G3J7

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. Floor plan can be download in document.

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431 Roxton Rd, Toronto, Ontario M6G3R5

Opportunity is knocking on this home. Currently the home is divided into two apt units. The Renovated Main Floor and Basement (2-3 Bdrm) apt & 2nd and 3rd floor (3-4 Bdrm) apt.  Possibilities abound, live in one unit and rent the other to help pay the mortgage or convert back to single family home with potential basement ensuite or just leave as-is and continue to rent out the two apartments.  There is really no need for parking as this home is very close to the Ossington Subway station and multiple transit options. Still you need parking? Then this home has 2 parking spots depending on your size of car, access located from laneway.  Fenced in backyard with shed included. There have been many recent upgrades to this home both past and present.  Possible Seller assisted financing.

257 Concord Ave, Toronto, Ontario M6H2P4

This versatile three-storey home offers fantastic income potential and multiple options for future expansion. Each floor features two bedrooms and a full kitchen. The fully finished basement with separate entrance has four bedrooms, a kitchen, and two bathrooms. Many opportunities to change the floor plan or build additional living space. At the rear of the property, a laneway-access double garage offers potential for constructing a two-storey, 800-square-foot laneway suite. Situated just steps from the TTC and close to the University of Toronto, George Brown College, Toronto Western Hospital, supermarkets, restaurants, and countless amenities, this property is ideal for investors or families seeking both convenience and significant rental income. Don't miss this rare opportunity!

598 Bathurst St, Toronto, Ontario M5S2P9

Welcome to a classic Toronto home in the heart of Palmerston-Little Italy, offering exceptional versatility for both investors and end users. Currently configured as three self-contained units, each with its own kitchen and bath, this property presents an excellent opportunity to generate rental income or live comfortably while offsetting expenses. Spanning three levels, each with separate entrances, bright & functional layouts. Separate laundry room with coin operated washer/dryer(2025) and separate hot water tank(2025). The detached two-car garage off the laneway adds rare value and potential for additional income if converted to a coach house (buyer to verify). Enjoy Toronto's most desirable amenities right at your doorstep - steps to Bloor, College, and Harbord, surrounded by trendy cafés, parks, and convenient transit options that make this location truly unbeatable. Whether you're an investor seeking a turnkey income property or a homeowner looking for a flexible live-and rent setup, 515 Ossington Avenue offers endless potential in one of the city's most sought-after neighborhoods.

515 Ossington Ave, Toronto, Ontario M6G3T3

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 Rd, Toronto, Ontario M6G3R2

Spectacular modern design masterpiece offering nearly 2,100 sq. ft. ofluxurious living space! Immerse yourself in elegance with the highest level offinishes and exquisite craftsmanship throughout. Main Level: Oversized livingand dining rooms, perfect for entertaining, alongside a nice kitchen with alarge island. Striking modern glass staircase with luminous LED lighting addsa dramatic touch. Family Room: Walk-out to a spacious deck, ideal forindoor-outdoor living. Primary Suite: Upscale retreat featuring a largewalk-in closet and spa-inspired Ensuite with heated floors. Bedrooms: Threeadditional bedrooms, each with unique design details, sharing a stylishbathroom with heated flooring. Lower Level: Breathtaking basement with 1 LargeRecreation, 1 guest bedroom, and a full 4-piece washroom. Features: Heatedfloors in all bathrooms, high-efficiency furnace , manifold water supply, andfoam insulation throughout. Hot water tank owned.

673 Crawford St, Toronto, Ontario M6G3K1

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, cafés, 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 Ave, Toronto, Ontario M6G2V7

Absolutely perfect Palmerston/Little Italy legal Duplex steps from Bloor street overlooking famed Christie Pits Park. Perfect as full investment, live/rent or multi generational. Even zoning for different commercial uses opening the door to various legal options. No tenants to assume! PROPERTY NOW VACANT!  Currently divided into 2 two-storey units seamlessly combining chic modern renovations with sought after mechanical upgrades. Choose whatever use suits you best. Benefit from extremely high rent of roughly $93,000 - $102,000 per year depending on property use, WOW! Main floor/lower features a light filled open concept design highlighted by the original exposed brick, hardwood floors and gas fireplace. One of a kind restaurant style kitchen with commercial appliances and walk out to professionally landscaped urban oasis. 2nd/3rd 2 bedroom, 2 bath offers a sun drenched eat in kitchen, large principle rooms and incredible roof top terrace potential! Enjoy a private courtyard like front entrance on iconic Montrose Ave and take advantage of this perfect location to further tailor this gem to suit your needs! Live and rent, full investment, Live and work, convert to single family...the possibilities are endless!!! Enjoy living in the heart of Toronto with elite access to Bloor St, Beautiful Parks, Delicious Restaurants, Boutique Shops, Nightlife, Community Centres and Coveted Schools. This is the property you always dreamed of and now it could be yours! Don't miss out!

490 Montrose Ave, Toronto, Ontario M6G3H1

A Re-Mark(ham)-able Opportunity in Little Italy - serious space, superb location, and fully move-in ready. Freshly introduced at a new price, 555 Markham St is a rare blend of history, design, and day-to-day practicality. Nearly 3,900 sq ft across four renovated levels provides generous, flexible space for modern family life.  Engineered wide-plank hardwood, updated windows, and abundant natural light set an elegant tone. The expansive kitchen, with a striking island and concealed walk-in pantry, flows to a sunken family room overlooking the private garden. Upstairs, five spacious bedrooms span two levels, including a top-floor bedroom with a deck and skyline views. A finished lower level with excellent ceiling height offers recreation or guest potential, while modern mechanicals, including a Viessmann high-efficiency boiler and ductless A/C, ensure year-round comfort. A two-car garage and completed laneway-suite feasibility study extend the options even further. Now newly priced, vacant, and ready for its next chapter, 555 Markham St is a Re-Mark(ham)-able opportunity to secure lasting space and value in the heart of Palmerston-Little Italy, steps from the subway and the reimagined Mirvish Village.

555 Markham St, Toronto, Ontario M6G2L6

Welcome to 53 Jersey Avenue where Toronto living actually checks all the boxes you keep saying you want. Detached home with a massive extension? Yep. Private driveway with parking for four? Obviously. A 2.5-car garage so oversized you could turn it into another two bedroom unit. a garden suite, or just the most obnoxious man cave on the block? Done. Inside, you've got not one but two fully renovated units: a 3-bed on the main with bonus basement space, and a 2-bed upstairs with a gas fireplace and private decks. And if you're worried about location don't. You're literally a 5-minute walk from College Street patios, like Cafe Diplomatico, Harbord cafes, dog parks, playing fields, pools, Little Italy, Little Portugal, Little Korea basically, all the best neighbourhoods you always wanted to live close to are now that much closer. This isn't just a house, its an income property, a lifestyle flex, and a chance to finally make your friends jealous when they come over. With a Walk Score of 96, Transit Score of 93, and Bike Score of 100, you (or your tenants) will have unmatched access to culture, parks, dining, and transit.

53 jersey Ave, Toronto, Ontario M6G3A4

In the heart of the city yet set within a quiet, tree-lined neighborhood, this fully renovated 4,200 square foot residence captures the best of both worlds. Every inch has been reimagined from top to bottom with modern finishes and timeless style, creating a home that is both sophisticated and welcoming. High ceilings and light-filled spaces set the tone, while the thoughtful design ensures seamless flow and effortless living. The interiors showcase refined craftsmanship throughout, from the beautifully redesigned kitchen with premium details to versatile spaces that adapt to both entertaining and everyday life. Upstairs, spacious bedrooms feature spa-inspired bathrooms and generous storage, while landscaped outdoor spaces offer a serene backdrop for relaxation just steps from the city's energy. At the rear, a stunning two-storey laneway home further enhances the property's prestige and flexibility. With its own entrance, secure garage, and a bright one-bedroom suite complete with kitchen and bath, it is ideal for multi-generational living, guest accommodations, a private workspace, or valuable income potential. Everything the city has to offer, from acclaimed restaurants and neighbourhood parks to convenient grocery stores and public transit, is just steps from your door. Together, the main residence and laneway home present a rare opportunity where luxury, location, and lifestyle converge in perfect harmony.

444 Roxton Rd, Toronto, Ontario M6G3R4

Vacant Lot - Great Opportunity In Desirable Little Italy! 16 x 128 Foot Lot. Vacant & Unserviced Lot. Notice of Decision from Committee of Adjustment for lot severance and for a new three storey detached dwelling with two storey semi-detached laneway suite, in the rear yard. Laneway At Rear of Property. Buyer is responsible for development charges, servicing costs, obtaining building permits and all other costs and fees. HST is in addition to the purchase price.

89A Clinton St, Toronto, Ontario M5G2Y4

Welcome to lofts at 707 Dovercourt, 5 Story Boutique Building. Extremely well maintained, mostly owner occupied building. Just south of Bloor St W. Short walk to Ossington Subway station. Modern Kitchen with sleek cabinetry, sunny bright unit with exposed concrete ceilings with w/o to private east facing balcony. Enjoy ensuite laundry, long gallery hallway with 1 parking spot. Experience urban living at its finest in one of the most sought after neighbourhoods. Bloorcourt Village steps to unique Shops, trendy cafes and restaurants. Great opportunity to get into the market.

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215 707 Dovercourt Rd, Toronto, Ontario M6H0B5

Welcome to one of Toronto's most vibrant and sought-after neighbourhoods, Little Italy. Nestled on a quiet, tree-lined street just steps from College Streets restaurants, cafes, and shops, this charming but dated semi-detached offers incredible potential for transformation. Whether you're an investor or a growing family looking to plant roots, this property presents a unique opportunity to renovate and customize a home with authentic character in one of the city's most desirable pockets.

464 Euclid Ave, Toronto, Ontario M6G2S9

Spacious 3 Storey Semi in the heart of vibrant Little Italy. Nestled on a tranquil, tree-lined street, this spacious home sits on a rare 20-foot-wide lot and offers the perfect blend of a charming retreat, and city living. With 4 generous-sized bedrooms-including the option to use the fourth as a separate family room-there's plenty of room to grow and adapt to your family's needs. The extra-large main floor eat-in kitchen is ideal for family gatherings or entertaining friends, while three kitchens (one on each level) and a wet bar on the third floor provide flexibility for multi-generational living or rental potential. Step outside and enjoy three balconies, a private backyard, and a large shaded front porch-offering multiple outdoor spaces to relax and take in the neighbourhood's peaceful atmosphere. The third-floor balcony showcases beautiful city views, making it the perfect spot to unwind at the end of the day. Additional highlights include a separate laundry room, ample storage in the basement, and a2-car garage with laneway access. As a designated duplex with separate backyard entry, this property offers incredible versatility-whether you're looking to live in, rent out, or create your dream home in one of Toronto's most sought-after communities. Steps to College Street shops, restaurants, public transit and great schools, you won't want to miss this exceptional opportunity to own a piece of Little Italy charm with endless potential.

244 Grace St, Toronto, Ontario M6G3A6

Welcome to 278 Clinton Street, a semi-detached home legally registered as a duplex in one of Toronto's most sought-after neighbourhoods. A fantastic opportunity for contractors, investors, & end-user buyers looking to customize a property to their own style & needs. The main floor features a spacious & open concept living & dining room with soaring 9.5 ft ceilings & preserved original details including hardwood flooring, wood casing, oversized baseboards, & crown moulding. With 3 bedrooms & 2 full bathrooms, plus a basement with a separate entrance that has been underpinned to provide excellent ceiling height, the home offers a flexible layout with unlimited potential. Further, the attic holds the possibility of becoming an additional half storey or loft space (buyers to complete their own diligence). Updates include New Roof (2024), New Eaves & Downspouts (2024), New Hot Water Tank (2024), Newer Furnace (approx. 2015) and Newer Air Conditioning (approx. 2015). Situated steps to Bloor Street, Christie Pits Park, the TTC, Christie Subway Station, & with College Streets vibrant Little Italy, Koreatowns shops & restaurants, & the University of Toronto all nearby, the location is unbeatable. Rear parking (via laneway) for 1 car, though the owners have comfortably parked 2 cars for many years without issue. Blending family-friendly community living with the best of Toronto's urban lifestyle, this property offers a rare chance to transform a home in a prime downtown location.

278 Clinton St, Toronto, Ontario M6G2Y6

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 sophisticated encapsulated in this labor of love. 3rd level's open concept suite with large rear terraces offers unobstructed city views and CN tower. *EXTRAS** Please see feature sheets for full home details. Builder offers Tarion new home equivalent warranty.

539 Crawford St, Toronto, Ontario M6G3J9

A Rare Opportunity To Own A Legal Triplex In The Heart Of Palmerston-Little Italy, Steps Away For Christie Park, Christy Subway Station, Vibrant Bloor St. And Local Schools, Shopping And Dining. The House Was Renovated In 2022 With High-End Finishes And Impeccable Craftsmanship And Attention To Details. Custom Large Windows Throughout And High Ceilings Create Bright And Modern Space That Combine Style And Comfort. Each Unit Has Its Own Separate Entrance And En-Suite Laundry And Ample Storage, Offering Convenience And Privacy. The Main Floor Unit Is A One Bedroom With An Open-Concept Kitchen And Living Area, Perfect For Entertaining Or Working From Home. The Upper Unit Spans The Second And Third Floors, With Two Bedrooms & Den, Two Luxurious Bathrooms, And A Huge Sunny Balcony Ideal For Outdoor Gatherings. Foam Insulated Exterior Walls Leading To Lower Heating & AC Bills. Brand New Pressure Treated Wood And Metal Railing In Balcony And Veranda. The Lower-Level Unit Is A One Bedroom And One Bathroom. The House Has 2 Parking Spaces And Great Potential For A Laneway Suite. This Is A Versatile Property Ideal For Investors And End-Users With Potential To Convert Back Into A Single-Family Home

351 Clinton St, Toronto, Ontario M6G2Y7

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.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.