Cabbagetown-South St. James Town Homes with 100+ Approx Age

Cabbagetown-South St. James Town Homes with 100+ Approx Age

Welcome to Cabbagetown-South St. James Town, an enchanting neighborhood nestled in the heart of Toronto, Ontario. Renowned for its rich history and vibrant community spirit, this area is a hidden gem that beautifully marries the charm of yesteryears with the conveniences of modern living.

Cabbagetown, named for the cabbage farms that once thrived here, boasts some of the city’s most picturesque streets, lined with stunning Victorian homes that date back over a century. With many residences exceeding 100 years in age, you’ll find an array of architectural styles, from classic brick facades to intricate woodwork, each telling a story of its own. These homes not only provide a glimpse into Toronto’s architectural heritage but also create a unique and inviting atmosphere that residents cherish.

Beyond its historical allure, Cabbagetown-South St. James Town is a community brimming with life. The area is home to lush parks, vibrant local markets, and an eclectic mix of cafes and boutiques that cater to every taste. Residents enjoy the convenience of nearby amenities, including grocery stores, schools, and public transport, making it easy to navigate the city.

The neighborhood's strong sense of community is evident through various events and festivals held throughout the year, fostering connections among residents and celebrating the area’s diverse culture. Whether you’re a first-time homebuyer or looking to settle down in a historic enclave, Cabbagetown-South St. James Town offers an irresistible blend of charm, character, and community that makes it a truly special place to call home.

Newest Cabbagetown-South St. James Town 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
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
$1,899,900
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
$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
$1,799,900
6 Beds ⋅ 4 Baths ⋅ C13152204 MLS
5.8% cap rate! Rare opportunity to acquire a fully gutted and renovated, turnkey four-unit investment property in the heart of downtown Toronto, offering a strong 5.8% cap rate and exceptional attention to detail throughout. Extensively upgraded while preserving the building's historic character. Upgrades include custom Ohio-made heritage brickwork (2023) matched to the original 1890 brick dimensions, newer peak roof shingles (2024), updated ABS drain systems with backflow prevention (2022), an interior weeping tile system (2022), and enhanced exterior stormwater drainage infrastructure (2022), new eaves (2023)The property features four fully gutted and renovated (2022/2025/2026) self-contained furnished apartments with separate entrances, modern finishes, programmable touchpad entry systems, centralized internet/network infrastructure, security cameras, a Doorbird smart entry system, forced air gas heating and A/C, and legal fire safety systems approved by certified installers. Units include a mix of private decks, BBQ areas, skylights, heated flooring (Apt 2 - bedroom only), a gas fireplace, in-suite laundry, and updated kitchens and baths. Currently configured as: 2 x two-bedroom units, 1 x one-bedroom unit, 1 x two-level owner's suite. Ideal for investors seeking stable income, furnished rental potential, multi-generational living, or short/mid-term rental opportunities (buyer to verify use). One rear parking space included. Offered substantially furnished with only limited exclusions. One uit (owner occupied) will be vacant on closing.

210 Gerrard Street E, Toronto
$1,799,900
4 Baths ⋅ C13152164 MLS
5.8% cap rate! Cabbagetown Heritage zone. Rare opportunity to acquire a fully gutted and renovated, turnkey four-unitinvestment property in the heart of downtown Toronto, offering a strong 5.8% cap rate andexceptional attention to detail throughout. Extensively upgraded while preserving thebuilding's historic character. Upgrades include custom Ohio-made heritage brickwork (2023) matched to the original 1890 brick dimensions, newer peak roof shingles (2024), updated ABS drain systems with backflow prevention (2022), an interior weeping tile system (2022), and enhanced exterior stormwater drainage infrastructure (2022), new eaves (2023).The property features four fully gutted and renovated (2022/2025/2026) self-contained furnished apartments with separate entrances, modern finishes, programmable touchpad entry systems, centralized internet/network infrastructure, security cameras, a Doorbird smart entry system, forced air gas heating and A/C, and legal fire safety systems approved by certified installers. Units include a mix of private decks, BBQ areas, skylights, heated flooring (Apt 2 - bedroom only), a gas fireplace, in-suite laundry, and updated kitchens and baths. Currently configured as: 2 x two-bedroom units 1 x one-bedroom unit 1 x two-level owner's suite. Ideal for investors seeking stable income, furnished rental potential, multi-generational living, or short/mid-term rental opportunities (buyer to verify use). One rear parking space included. Offered substantially furnished with only limited exclusions. One unit (owner occupied) will be vacant on closing. Property listed as Heritage.

210 Gerrard Street E, Toronto
$3,459,000
6 Beds ⋅ 5 Baths ⋅ C12920390 MLS
Stunning 1840 Victorian Mansion in the heart of Cabbagetown. This unique Live/Work space features soaring ceilings, original plasterwork, and a sun-drenched vaulted loft with large windows and bright exposures. Experience the perfect blend of historic character and modern functionality, including a spacious main floor office. Steps to the Eaton Centre and downtown, yet offering a private gated garden shaded by mature trees and fencing. Perfectly situated next to municipal parking for easy client access.

413 Sherbourne Street E Unit 3+, Toronto
$1,399,000
4 Beds ⋅ 3 Baths ⋅ C12853178 MLS
Perfectly located on the superior side (East of Parliament) of Toronto's iconic Cabbagetown, this exquisite semi-detached character home offers a picturesque living experience akin to residing within a lush park. Surrounded by charming Victorian heritage homes, well-manicured lawns, whimsical laneways, parks & walking paths, you'll find peace & tranquility alongside hip restaurants & shops. Proper duplex with separate metering makes for a savvy investment opportunity with a net annual income of approx. $60k (gross $77k).Excellent opportunity to live in one unit & rent out the other for extra income. Upper level is vacant, while the main level is occupied by market rate tenants on a month-to-month basis, ensuring flexibility for the new owner to take full possession. Elegant interior is adorned with oak hardwood floors, crown mouldings & high ceilings create a warm & inviting ambiance, while newer kitchen features chic cupboards, stylish backsplash, granite countertops & stainless steel appliances. Breakfast/dining area is a true highlight overlooking a front porch which provides a delightful view of Wellesley St, perfect for enjoying morning coffee. The living area features a cozy built-in bench window bench. Walk-out to private backyard for outdoor relaxation & entertaining, while conveniently located main floor powder room is both stylish & functional. Oak staircase leads down to generously sized bedrooms. Lower level is a true retreat, showcasing high ceilings & spa-like 4-piece bathroom with marble, heated flooring for cozy comfort. Ample closet spaces in both rooms & separate laundry area. 2nd level apartment has 2 large bedrooms, 4pc washroom & modern kitchen combined with a living area that flows seamlessly to oversized New Orleans style balcony looking over the tree lined heritage district (grants available). Separate furnace, air conditioning and laundry for each unit. Easy access to highways & transit. Main Unit Photos Are Virtually Staged

412 Wellesley Street E, Toronto
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