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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

$3,299,000
6 Beds 5 Baths C13562684 MLS
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.

452 Montrose Avenue, Toronto

$3,549,000
C13559310 MLS
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.

427 Crawford Street, Toronto

$3,549,000
12 Beds 6 Baths C13559278 MLS
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.

427 Crawford Street, Toronto

$1,799,900
2 Baths C13558428 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, 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.

725 Dovercourt 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

$2,599,000
5 Beds 4 Baths C13488148 MLS
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!

730 Shaw Street, Toronto

$3,400,000
5 Beds 7 Baths C13482698 MLS
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.

458 Markham Street, 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

$2,250,000
5 Beds 4 Baths C13471464 MLS
Visit REALTOR website for additional information. Exceptional investment opportunity in the heart of Toronto's highly sought-after Little Italy/Palmerston neighbourhood. This legal fourplex has been extensively renovated and meticulously maintained, offering a rare combination of strong existing income, vacant units for immediate upside, and outstanding long-term appreciation potential. Featuring four self-contained suites, each with its own heat source with no shared air ducts; each suite also has its own hydro meter, in-suite W/D, dishwasher, and built-in microwave. Two units are tenanted, while two vacant units offer the flexibility to select your own tenants at current market rents or occupy one unit yourself while generating substantial income from the others. The thoughtfully configured layout includes a spacious 1-bed, 1-bath basement apartment in a professionally underpinned (8ft ceiling) lower level; a bright 2-bed, 1-bath main floor suite; a 1-bed, 1-bath second-floor apartment; and a unique upper two-level 1-bed, 1-bath suite spanning the second & third floors; in total, 5 bedrooms and 4 bathrooms across four legal units. Extensive upgrades and renovations throughout deliver turnkey ownership with pride of ownership at every turn; two on-site parking spaces add to tenant appeal and owner convenience. Steps from College Street's renowned restaurants, cafés, boutiques, parks, and transit, this vibrant west-end neighbourhood continues to attract quality tenants and homeowners alike; enjoy easy access to Little Italy, Bickford Park, Christie Pits, KensingtonMarket, UofT, & downtown. Whether you're an investor seeking immediate cash flow and future rental upside or an owner-occupier looking to offset your mortgage with rental income, this is a rare opportunity to acquire a legal, fully upgraded multi-unit property in one of Toronto's most desirable urban communities. (43405081)

486 Montrose Avenue, 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

$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

$1,298,000
4 Beds 3 Baths C13234998 MLS
Exceptional opportunity in one of Toronto's most coveted west-end neighbourhoods, perfectly situated mere steps from the Bloor Subway Line. This meticulously maintained and thoughtfully updated property offers exceptional versatility, featuring three independent units - ideal for savvy investors, multi-generational families, or homeowners looking for significant supplementary income potential.Step into a truly turnkey property, each unit updated with contemporary style. The main floor unit showcases a stunningly renovated kitchen with SS Appliances and a breakfast bar, high ceilings and the convenience of dedicated in-suite laundry. In the bright 2nd floor unit you'll also find private laundry and a lovely sunny wood deck featuring views of the CN Tower - the perfect urban oasis. The third comfortable living space adds further flexibility and appeal to this unique offering.Designed with occupant comfort in mind, the residence features soundproofing between units. Practicality meets potential with a valuable garage accessible via the laneway, providing secure parking and generous storage. Immerse yourself in the heart of the dynamic Bloorcourt/Ossington community. Your new address places you within a short stroll of some of the city's most celebrated restaurants, trendy cafés, independent boutiques, vibrant parks, and lively nightlife. Enjoy seamless connectivity with the Bloor subway line and dedicated bike routes just moments away, offering quick access to downtown Toronto and beyond.This is more than a property; it's a rare, turnkey offering in an unbeatable location, brimming with exceptional flexibility and endless possibilities to live, invest, and thrive in one of Toronto's most desirable urban pockets.

679 Ossington Avenue, Toronto

$5,990,000
C13170018 MLS
Rare investment opportunity on bustling College Street just west of Bathurst Street in one of downtown Toronto's most vibrant and sought-after commercial corridors. Attractive mixed-use property featuring a Michelin-recommended restaurant/hospitality tenant with inviting front patio at grade, generating strong street presence and appeal. Upper floors offer versatile modern office space configurations including three self-contained second-floor units and a bright, light-filled third-floor office currently occupied by a single tenant. Property also features two rear parking spaces plus dedicated locker space for each office unit and shared laundry area in the rear basement. Fantastic downtown Toronto location near major TTC transit, leading hospitals, the University of Toronto, Kensington Market, and countless outstanding area amenities.

460 College 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

$1,699,000
5 Beds 4 Baths C13162902 MLS
Welcome to 588 Ossington Avenue, a rare opportunity to own a dynamic, income-generating property in the heart of Palmerston-Little Italy-one of Toronto's most vibrant and consistently high-demand rental locations. The property is currently configured as four self-contained units, offering multiple income streams and strong flexibility for investors or end-users looking to offset carrying costs. The main floor features a spacious 1+den, 1-bath suite with additional recreational space on the lower level and direct access to a large backyard. The basement includes a separate self-contained bachelor Suite. The second level offers a bright 1+den suite with a private balcony, while the third floor hosts a well-sized 1-bedroom unit. The third-floor tenant is currently on a month-to-month basis, with the remaining units vacant-providing immediate flexibility for leasing or end-user occupancy. Based on current market conditions and rental assumptions, the property presents the potential for an attractive return profile, with cap rate performance that may approach or exceed the 5% range; buyers are advised to conduct their own due diligence. This home offers a turnkey opportunity with limited immediate capital requirements. Features include three separate hydro meters, individual climate control, updated windows, and modern interior finishes throughout. A standout feature is the two-car garage with rear laneway access, significantly enhancing both functionality and tenant appeal. Positioned just steps to Ossington's renowned restaurants, cafes, parks, and transit, this location supports exceptional walkability, strong rental demand, and long-term growth potential.An outstanding opportunity to secure a well-located downtown asset with income-generating potential.

588 Ossington Avenue, 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

$1,175,000
3 Beds 3 Baths C13150742 MLS
Location! Location! Location! Welcome to Clinton St. in the Heart of Little Italy! An end-row property offering the distinct feel of a semi-detached dwelling. Cared for by the same family for over 50 years, this home now awaits your personal touch! Bright and spacious dwelling with great potential! The main level features living & dining areas with hardwood flooring; large eat-in kitchen with ceramic tiling overlooking the family room; 1x3pc main level bathroom and a large sunroom with a walkout to the rear yard! Upper level comprises three good sized bedrooms and one 4-piece common bathroom. Endless potential in the basement with a 1x4pc. bathroom, laundry sink, and a separate entrance with a walk-up to the side yard. Great-sized lot to enjoy a private, fenced backyard and a desirable detached two-car garage with rear laneway access. This home is steps away from some of Toronto's most iconic restaurants, local cafes and boutique shops on both trendy College St. to the south and Harbord St. to the north. For those who value community, it provides families convenient access to elementary & secondary schools, essential amenities, and city green spaces. It's more than just a neighbourhood-it's a lifestyle for people looking to be in the vibrant community of Palmerston- Little Italy! This is where you want to be! Do not miss out! Property is being sold in "as is" condition with no representations or warranties from the Seller or Listing Brokerage. Some photos have been virtually staged/virtual lawn.

215 Clinton Street, Toronto