Toronto C08 Homes with 100+ Approx Age

Toronto C08 Homes with 100+ Approx Age

Welcome to Toronto C08, a vibrant and dynamic neighborhood nestled in the heart of Canada’s largest city. This area is not only rich in culture and diversity but also boasts a unique architectural heritage, with homes that have stood the test of time. Many residences here are over 100 years old, offering a glimpse into the city’s storied past while providing modern conveniences for today’s homeowners.

Toronto C08 is characterized by its charming tree-lined streets and an eclectic mix of historic and contemporary buildings. The historic homes, often featuring intricate details and classic designs, reflect the craftsmanship of a bygone era. From Victorian-era houses to Edwardian masterpieces, each property tells a story and adds to the neighborhood's character. Living in a home with such history not only provides a sense of connection to the past but also a unique opportunity to be part of a community that values its heritage.

The neighborhood is also known for its vibrant arts scene, bustling markets, and an array of dining options, making it a perfect place for families and young professionals alike. With easy access to public transit, parks, and schools, Toronto C08 is a highly sought-after area for those looking to experience the best of urban living while enjoying the charm of historic homes.

If you’re searching for a place that combines the allure of history with the excitement of modern city life, look no further than Toronto C08. Discover your dream home in this captivating neighborhood and become part of its rich tapestry!

Newest Toronto C08 Homes with 100+ Approx Age

$3,400,000
4 Beds ⋅ 4 Baths ⋅ C13578164 MLS
The finest 4-plex in Cabbagetown has returned to market for the first time in a generation! This impeccably maintained and professionally updated income property has been meticulously renovated and represents a rare opportunity to acquire a best-in-class asset of this stature in one of Toronto's most storied neighbourhoods. Over 4200+ sq ft of living space, complimented with multiple walk-out exterior spaces including 2x large private decks, a rear walk-out patio at grade, and a stunning oversized south facing rooftop terrace on the upper level overlooking lush rear grounds under a densely treed canopy. The building is home to a high-quality tenant base, and each suite enjoys dedicated climate controls. The building has been curated to appeal to professionals and offers living spaces that are ideal for both entertaining and relaxing in a quiet environment. Fine interior finishes include hardwood floors, updated bathrooms, updated kitchens, high ceilings, and large windows. Each unit has dedicated ensuite laundry. Parking is accessed via a private rear laneway off of Aberdeen Ave, including 4 parking spaces at present (of which 1 is a tandem parking space,) and the possibility exists to expand up to 6 car parking on site). 29 Winchester has been assembled to remain highly desireable and strongly appealing to tenants in any market. This premium location is steps to restos and shopping along Parliament Street, and accessible to multiple TTC options (including the Carlton Street Car) or a short walk to Castle Frank Station TTC Subway. Tenants can enjoy Winchester Park at their doorstep, or stroll to Riverdale farm. Mere minutes to the downtown core and Distillery District / St Lawrence Market. Shows 10+ and must be seen - a perfect addition for any investor seeking a high calibre investment grade property to add to their portfolio.

29 Winchester Street, Toronto
$1,899,900
7 Beds ⋅ 4 Baths ⋅ C13566570 MLS
Welcome to 499 Ontario Street, a spectacular, fully renovated legal duplex in the heart of historic Cabbagetown. The ultimate turnkey opportunity for investors, multi-generational families, or live-rent buyers, this property seamlessly blends classic character with high-end modern design. Step inside to discover soaring ceilings, stunning exposed brick accents, gorgeous marble floors, and premium contemporary finishes throughout. The building is divided into two well-appointed, self-contained residences, each featuring independent ensuite laundry, gourmet kitchens with sleek stainless-steel appliances, and rare, private outdoor spaces. The upper unit is a sun-drenched sanctuary boasting 3 spacious bedrooms, 2 elegant bathrooms, and a spectacular private rooftop deck perfect for relaxing above the city. Below, the main-floor and lower-level suite offers a beautifully executed 4-bedroom, 2-bathroom layout, complete with direct walk-out access to its own private, fully fenced yard. To top it off, this property includes a highly coveted two-car parking pad at the rear-an absolute premium in this historic downtown neighbourhood. Perfectly positioned just steps from vibrant shops, cafes, and patios of Parliament Street, scenic local parks, and transit - this exceptional asset delivers the perfect combination of location, modern luxury, and incredible cash flow.

499 Ontario Street, Toronto
$1,495,000
3 Beds ⋅ 2 Baths ⋅ C13565128 MLS
Live on one of Toronto's most sought-after streets! This beautifully renovated 2-storey home offers over 2,053 sq. ft. of finished living space (including the basement), featuring 3 bedrooms, 2 bathrooms, and the rare convenience of private parking.Thoughtfully and meticiously renovated from top to bottom, this home perfectly blends timeless character with elegant modern finishes. The open-concept main floor is ideal for everyday living and entertaining, highlighted by a stunning kitchen with stainless steel appliances and seamless access to the maintenance-free, west-facing backyard-perfect for relaxing or hosting guests.Upstairs, you'll find spacious bedrooms filled with natural light. The fully underpinned and waterproofed basement represents a significant investment, with hundreds of thousands spent to create additional living space complete with a large recreation room, a stylish 3-piece bathroom, and abundant storage.

40 Bright Street, Toronto
$1,495,000
4 Beds ⋅ 2 Baths ⋅ C13563956 MLS
In one of Cabbagetown's most sought-after locations, this beautifully proportioned three-storey Victorian, built in 1880, offers nearly 1,900 square feet above grade and an opportunity to put down roots in one of Toronto's most cherished neighbourhoods. Lovingly maintained and comfortably liveable today, it offers an exceptional combination of character, space and location from the moment you move in.Behind its classic façade, high ceilings on all three levels, period fireplaces, stained glass and beautifully proportioned rooms reflect the home's Victorian origins, while a practical four-bedroom layout and flexible living spaces are equally well suited to today's family life.Situated on the preferred south side of Wellesley Street East, the property enjoys excellent natural light and the deeper lots that distinguish this stretch of the street, accommodating a private garden, charming garden shed and coveted laneway parking without compromising outdoor living space. The home has been well cared for over the years, with updated electrical and plumbing systems and a solid structure, providing an excellent foundation for future improvements while allowing the next owner to personalize at their own pace.Parliament Street's cafés, restaurants, independent shops and everyday conveniences are just steps away. Riverdale Farm, Wellesley Park, the Don Valley trail network, excellent schools and downtown Toronto are all within easy reach, while Cabbagetown's beautifully preserved Victorian streetscapes and strong sense of community continue to make it one of the city's most beloved neighbourhoods.Homes like this offer what's increasingly difficult to find: authentic Victorian character, beautifully proportioned living spaces, an exceptional south-side lot with laneway parking, and one of Toronto's most enduring neighbourhoods.

347 1/2 Wellesley Street E, Toronto
$1,950,000
5 Beds ⋅ 4 Baths ⋅ C13561126 MLS
Discover a rare opportunity to own a legal, city-approved triplex that perfectly balances historic Toronto charm with high-end modern design. Extensively gutted and renovated from the studs in 2019, this turnkey property offers close to 3,000 square feet of thoughtfully optimized living space across three distinct, self-contained suites. This is a truly seamless addition to any investment portfolio or an ideal live-and-rent scenario. Behind the timeless brick facade, the home has been completely transformed. The 2019 renovations included modernized kitchens with quartz countertops, updated bathrooms, new windows, lighting, staircases, and a professionally underpinned lower level excavated to increase the ceiling height. A brand-new roof was installed in 2023. The property features three separate hydro meters, three gas meters, and dedicated laundry in every unit. The upper-level two-bedroom, two-bathroom suite is bathed in natural light from a striking skylight and blends modern finishes with beautifully preserved original red brick walls. It boasts a private balcony off the primary bedroom, a massive accessible attic for rare urban storage, and its own furnace and central air conditioning. The main-level one-bedroom suite features a bright, inviting layout highlighted by a charming, working wood-burning fireplace and a walk-out to a private outdoor patio. It is also serviced by its own furnace and central air. Accessed via a private rear entrance, the lower-level two-bedroom suite features warm exposed brick, high ceilings, modern vinyl flooring, and a bathroom with a sleek walk-in shower. Set on a deep lot with the potential to convert the rear garden into parking off the laneway, this exceptional triplex delivers flexibility, quality craftsmanship, and outstanding value.

366 Ontario Street, Toronto
$1,450,000
4 Beds ⋅ 2 Baths ⋅ C13538714 MLS
A rare offering in historic South Cabbagetown, this impeccably renovated solid brick Edwardian semi seamlessly blends timeless architecture with elevated modern design. Move-in ready and exceptionally stylish, this 3+1 bedroom, 2 bathroom residence offers sophisticated living across four beautifully curated levels. The sun-drenched main floor is designed for both effortless entertaining and comfortable everyday living. Cozy up by the wood-burning fireplace in the inviting living room, or cook and gather in the stunning Parisian-inspired galley kitchen-a true showpiece featuring floor-to-ceiling cabinetry, premium JennAir stainless steel appliances, generous prep space, and striking steel-framed doors opening to the lush private backyard. Outside, a beautifully landscaped urban retreat awaits, with multi-level seating areas perfect for summer dinners, morning coffee, or evening cocktails under the stars. The second floor offers exceptional flexibility, with two spacious bedrooms, a beautifully renovated 4-piece bathroom with heated floors, and a thoughtfully reimagined middle bedroom now serving as a warm and inviting family room-ideal for movie nights, reading, or quiet retreat. Natural light pours down the center stairwell from the third-floor skylight, adding warmth and architectural charm throughout. The private third-floor primary suite feels like a serene treetop escape, complete with a separate dressing room/walk-in closet and a stylishly renovated ensuite bath. Additional highlights include a heated enclosed front porch with exceptional storage, a functional lower level with laundry and additional storage space, and the rare luxury of private laneway parking for one car. Set on one of Toronto's most beloved streets in the heart of historic Cabbagetown, just steps to Riverdale Farm, parks, transit, and the neighbourhood's vibrant cafes, restaurants, and independent shops. A turnkey city home with undeniable soul, style, and substance.

356 Ontario Street, Toronto
$1,390,000
3 Beds ⋅ 4 Baths ⋅ C13508230 MLS
*** LIVE-WORK-RENTAL INCOME Flexible Space *** PRICED TO SELL *** Discover a hidden treasure in this Victorian semi-detached home, perfectly situated on a private street in the vibrant downtown core of Bloor St East and the Howard Street Neighborhood. Here, historic charm meets contemporary convenience, surrounded by modern residential condos that enhance the areas appeal. Spanning three stories, this remarkable residence features three spacious bedrooms and four bathrooms, with the main floor effortlessly transitioning into a cozy office space. Thoughtfully and thoroughly renovated in 2004, this home strikes a beautiful balance between its storied past and the comforts of modern live-work flex space. The basement features a separate entrance and offers the potential to be easily converted into a one-bedroom rental unit for additional income or utilized as an in-law suite. With a fantastic walk score of 94, youll have easy access to the nearby TTC Sherbourne Subway Station, an Asian supermarket at Via Bloor Condos, No Frills, and Freshco, making it a breeze to explore everything the city has to offer. This Victorian gem is not just a home; its an exceptional opportunity for anyone looking to blend living and work in the heart of downtown Toronto. Minimum One unassigned street parking space available on Edgedale Road. Total 3,054 sq ft of living space.

9 Edgedale Road, Toronto
$1,390,000
3 Beds ⋅ 1 Baths ⋅ C13508232 MLS
*** LIVE-WORK-RENTAL INCOME Flexible Space *** PRICED TO SELL ***Experience the ultimate blend of work, office, and home life in this beautifully restored Victorian semi-detached residence, ideally positioned on a quiet private street in the bustling downtown core near Bloor St East and the Howard Street Neighborhood. This unique property offers a rare opportunity for seamless live-work flexibility: the main floor and lower level are thoughtfully designed to serve as a dedicated office or workspace, perfect for professionals or entrepreneurs seeking a productive environment without leaving home. Spread across three spacious stories, the home features three bedrooms and four bathrooms, with a layout that easily accommodates both family living and business needs. The fully renovated interior (2004) marries historic character with modern amenities, creating an inviting atmosphere for both work and relaxation. The separate basement entrance adds even more versatility, ideal for a private office, in-law suite, or conversion into a one-bedroom rental unit for additional income. With a stellar walk score of 94, you're steps from TTC Sherbourne Subway Station, grocery options like No Frills and Freshco, and the vibrant amenities of Via Bloor Condos. Surrounded by contemporary condos, this Victorian gem stands out as a rare chance to integrate your professional and personal life in downtown Toronto, offering the perfect setting for those who value both historic charm and modern live-work convenience. Minimum one unassigned street parking space available on Edgedale Road. Total 3,054 sq ft of living space.

9 Edgedale Road, Toronto
$1,899,900
5 Beds ⋅ 3 Baths ⋅ C13491242 MLS
Set In The Heart Of Sought-After Cabbagetown, This Impeccably Renovated Heritage Home Makes An Immediate Impression With Its Timeless Facade And Refined Presence. Inside, A Surprisingly Expansive Layout Unfolds With Over 1,900 Sq Ft Above Grade, Plus A Fully Finished Lower Level Designed For Flexible Living. The Main Floor Features Soaring Ceilings And A Bright, Open-Concept Flow, Anchored By A Generous Living And Dining Area Ideal For Hosting. Beautifully Finished Hardwood Floors Add Warmth And Sophistication Throughout. In Total, The Home Offers Over 2,600 Sq Ft Of Living Space, Including 700+ Sq Ft Below Grade, Seamlessly Blending Classic Character With Modern Luxury. Highlights Include A Well-Appointed Chef's Kitchen With Premium Appliances And Elegant Cabinetry, A Tranquil Primary Suite With A Spacious Spa-Inspired Ensuite, And A Thoughtfully Redesigned Rear Garden That Transitions Effortlessly From Convenient Parking To A Stylish Outdoor Setting For Entertaining.

328 Wellesley Street E, Toronto
$1,599,000
4 Baths ⋅ C13477752 MLS
End-user opportunity at 179 Queen Street East with vacant possession of the commercial component and the owner's suite on closing. A 3-storey, 3-unit mixed-use building on the Queen East corridor: main-floor and lower-level commercial (vacant); a fully renovated middle-floor 1-bedroom apartment (leased); and a 2-storey, 2-bedroom owner's suite on the top floor with a private rooftop terrace (vacant). Current ownership raised the main floor and opened up the basement, doubling the building's usable commercial envelope - what was a low-ceiling basement is now a second full storey of retail, paired with the existing main-floor retail. A future owner can occupy the entire commercial component across two full levels, or lease both floors to a single retail tenant, while moving into the top-floor owner's suite. The building has been fully rewired with two new electrical panels in the basement and new windows throughout. The middle-floor 1-bedroom is fully renovated with new appliances and in-suite laundry. A new staircase services the residential suites. Position: end-user-ready commercial plus owner-occupier suite, with stabilized middle-floor income. Directly across the street from the future Moss Park station on the Ontario Line, currently under construction - a rare chance to acquire a transformed mixed-use building at a future rapid-transit node before the station opens, with the long-term rerating's in foot traffic, retail rents, and residential demand that come with being steps from a new subway stop. Tenured Queen East corridor steps to the Distillery District and St. Lawrence Market, with a demand floor across daytime retail traffic, downtown professionals, and creative-sector tenants.

179 Queen Street E, Toronto
$2,180,000
5 Beds ⋅ 4 Baths ⋅ C13217618 MLS
Freshly Painted Elegant Victorian Residence On A Quiet, Sought-After Street In Cabbage Town. Rare Offering With Two Self-Contained Dwellings Under One Address-Ideal For End-Users Or Investors. Main House Features Over 3,000 Sq. Ft. Above Grade With 3+2 Bedrooms Includes 2 Ensuites And 4 Full Bathrooms. 10 Feet High Main Floor. Bright Open-Concept Main Floor With Hardwood Floors, Gas Fireplace, High Ceilings, And Pot Lights. Large Gourmet Kitchen Perfect For Entertaining. Spacious Primary Bedroom With 5-Pc Ensuite And Closet. Second Bedroom With Renovated Ensuite And Walk-In Closet. Third Floor Walkout To Private Deck; Large Front Porch Ideal For Outdoor Enjoyment. Finished Basement Includes 2 Bedrooms And Renovated Bathroom For Added Living Space. Newly Renovated (2026) Coach House At Rear Offers Approx. 1,760 Sq. Ft. Over 3 Finished Levels, With Private Parking And Courtyard. Features 2 Bedrooms On Second Floor, 2 Full Bathrooms, And Open-Concept Basement Recreation Room That Can Serve As A Third Bedroom Or Office. Combines Classic Victorian Charm With Modern Upgrades. Located In North America's Largest Preserved Victorian Neighborhood. Walking Distance To Parks, Schools, Transit, Shopping, And Restaurants.

42 Amelia Street, Toronto
$1,899,000
6 Beds ⋅ 3 Baths ⋅ C13153804 MLS
Spectacular Renovated Cabbagetown Victorian Duplex With High End Finishes. Featuring 10Ft Ceilings & Natural Bamboo Flooring Throughout & Beautiful Kitchens With Quartz Counters. 3 Luxurious Spa Baths, 7.5' Underpinned Basement With A Separate Front Walkout & Private Oasis Garden. Oversized Double Garage. Fantastic Investment Oppurtunity. Currently Leased To Great Tenants, Who Are Month To Month. Vacant Possession Also Available! Revenue Over $100,000 Per Year.

323 Ontario Street, Toronto
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