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, a vibrant and historic neighborhood nestled in the heart of Toronto, Ontario. Renowned for its charming streets and rich cultural tapestry, this area is a delightful blend of old-world charm and modern urban living. As one of Toronto’s oldest neighborhoods, many homes here boast a remarkable history, with properties dating back over 100 years, offering a unique glimpse into the architectural styles of the past.

Cabbagetown is famous for its beautifully preserved Victorian and Edwardian houses, characterized by their intricate detailing and lush gardens. Walking through the tree-lined streets, you’ll find a warm community atmosphere, where neighbors greet each other and local businesses thrive. The area is home to an eclectic mix of quaint cafes, artisanal shops, and vibrant eateries, making it a hub for food lovers and creatives alike.

In addition to its historic homes, Cabbagetown-South St. James Town is conveniently located near several parks and green spaces, perfect for families and outdoor enthusiasts. The nearby Riverdale Park offers stunning views of the city skyline, while the Don Valley Ravine provides endless opportunities for hiking and biking.

With its unique blend of heritage charm and contemporary conveniences, Cabbagetown-South St. James Town is not just a place to live, but a community to embrace. Whether you’re drawn to the architectural beauty of century-old homes or the lively neighborhood spirit, this area offers a truly enchanting lifestyle in the heart of Toronto. Come discover the magic of Cabbagetown today!

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
$1,799,900
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
$1,899,900
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
$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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