Annex Homes with 100+ Approx Age

Annex Homes with 100+ Approx Age

Welcome to the Annex, one of Toronto's most vibrant and historic neighborhoods! Nestled in the heart of the city, the Annex offers a unique blend of cultural richness and architectural beauty, making it a sought-after destination for both families and young professionals alike.

Known for its stunning Victorian and Edwardian homes, many of which boast an impressive age of 100 years or more, the Annex is a treasure trove for those who appreciate classic architecture. Walking through the tree-lined streets, you’ll be captivated by the intricate details of the homes, from ornate cornices to charming bay windows. This neighborhood not only showcases the elegance of a bygone era but also reflects the city's commitment to preserving its historical roots.

The Annex is more than just its beautiful homes; it’s a lively community filled with cafes, boutiques, and cultural institutions. Residents enjoy proximity to the University of Toronto, making it a hub for students and academics. The vibrant atmosphere is further enhanced by local art galleries, theaters, and music venues, offering endless opportunities for entertainment and engagement.

With easy access to public transit, including the subway, commuting to downtown Toronto or other parts of the city is a breeze. Parks and green spaces, such as the picturesque Philosopher's Walk, provide a breath of fresh air amid the urban bustle.

Whether you’re looking to buy a historic home or simply want to explore a neighborhood rich in character and charm, the Annex is a perfect choice. Experience the allure of this captivating community where history and modern life harmoniously coexist!

Newest Annex Homes with 100+ Approx Age

320 Brunswick Avenue, Toronto
$1,699,000
5 Beds ⋅ 4 Baths ⋅ C14088470 MLS
Attention Renovators, Investors & End Users! Imagine the possibilities. Set on a leafy stretch of Brunswick Avenue, overlooking a local playground in the heart of the Annex, this handsome solid-brick Edwardian is a rare opportunity to create a home that is uniquely your own.Full of character, space and potential, this substantial four-level property offers 3,302 square feet of living space and is currently configured as three self-contained units: a one-bedroom main floor, a three-bedroom second & third floor suite, and a one-bedroom lower-level apartment. Each has its own entrance, laundry and outdoor space.Whether your vision is a spectacular single-family home, a wonderful multi-generational residence or a smart investment with income potential, this property gives you the space and flexibility to bring that vision to life.The fully fenced 25 x 127-foot lot is a true urban treasure, complete with a detached two-car garage-an exceptional and increasingly rare feature in the Annex. The driveway is owned by the Neighbourhood Land Trust via Howland Avenue. There is no registered legal right-of-way to the garage; however, the owner has enjoyed uninterrupted use for 23 years. There is a possibility for a garden suite on this property.The maximum size of a permitted 2-storey as of right garden suite build appears to be 1,291 square feet total (over two floors, main and upper). This is the largest build possible for any property under the program, according to Laneway Housing Advisors. LOCATION! Step outside and you are immersed in everything that makes the Annex so special. Bloor Street is just moments away, with Metro, Shoppers Drug Mart, Weiners Hardware, the community centre, beloved restaurants, pubs, cafés and independent shops all close at hand. The University of Toronto is approximately a 15-minute walk away.A property with character, possibilities and a location that is impossible to replicate. Bring your vision and create something extraordinary.

320 Brunswick Avenue, Toronto
26 Bishop Street, Toronto
$1,875,000
3 Beds ⋅ 3 Baths ⋅ C14129164 MLS
Welcome to 26 Bishop Street, where sophisticated city living meets the charm and privacy of a beautifully renovated home in the heart of Yorkville Village. Nestled on a character filled, no- through street. Completely transformed with style and attention to detail, this exceptional 3-bedroom, 3-bathroom residence offers a rare opportunity to enjoy true turnkey living in one of Toronto's most coveted neighbourhoods. Step inside to beautifully curated interiors designed for both everyday living and effortless entertaining. Three spacious bedrooms and three beautifully appointed bathrooms provide exceptional versatility, while the private backyard creates your own peaceful escape in the city. Finished with elegant, low-maintenance stonework, it's the perfect setting for summer dinners, morning coffee or cocktails under the stars. Even more coveted in this location, your own private parking! And then there's the lifestyle. Step outside and experience the very best of Yorkville just moments from your door. Stroll to celebrated restaurants, charming cafes, designer boutiques, Whole Foods, Ramsden Park, Bloor Street and the TTC, with some of Toronto's finest shopping, dining and cultural destinations all within easy reach. Stylish, sophisticated and completely move-in ready, 26 Bishop offers something increasingly difficult to find in the city: the warmth and privacy of a home, outdoor space and parking, all wrapped in the unmistakable lifestyle of Yorkville.

26 Bishop Street, Toronto
154 Walmer Road, Toronto
$2,999,900
6 Beds ⋅ 4 Baths ⋅ C14128256 MLS
Set on one of the Annex's most prestigious, mature, tree-lined corridors, this home presents a rare and distinguished offering. Surrounded by multi-million-dollar historic estates this grand three-storey residence blends classic architectural with extraordinary future upside for the discerning buyer. Boasting an impressive 3,199 sq ft of above-grade living space on a substantial 32.38 x 128-foot lot, the home commands a striking street presence, further enhanced by the ultimate downtown luxury: a private double driveway and a 1-car garage, offering total parking for 3 vehicles. From the moment you enter, the main floor is designed for both grand-scale entertaining and seamless daily living with rich hardwood floors and brilliant natural light pouring through an abundance of windows. The impressive principal living and dining rooms flow naturally into a raised family room, creating an inviting, open ambiance. At the rear, a generously scaled, renovated kitchen features modern appliances and a walk-out to a newer private deck overlooking the secluded backyard. The second level hosts 3 well-proportioned bedrooms, anchored by a magnificent primary retreat. This expansive suite features an attached flexible bonus room-perfect for a home office, nursery, or a bespoke walk-in dressing room. A secondary bedroom on this level opens directly onto a private sundeck. Offering exceptional versatility, the self-contained third-floor apartment features a complete kitchen, living area, bedroom, 4-piece bathroom, and its own private walk-out to a newer sundeck-ideal for visiting guests, an executive home office, or a private nanny suite. While entirely move-in ready this home also presents a pristine blank canvas. Much like the stunning transformations seen at properties in the area and on the street, this home offers a rare generational opportunity. Move in and enjoy its classic charm immediately, or let your vision take shape to craft your ultimate downtown dream estate.

154 Walmer Road, Toronto
107 Macpherson Avenue, Toronto
$3,150,000
5 Beds ⋅ 4 Baths ⋅ C14116674 MLS
A Summerhill Gem | Space, Style & Sunlight Set on a coveted street in prime Summerhill, this beautifully updated, wide semi-detached home offers an exceptional blend of timeless character, modern design and effortless living. With four bedrooms, three bathrooms, a main-floor powder room and parking for two cars, this move-in-ready home delivers the space and flexibility to suit every stage of life. The open-concept main floor features engineered hardwood floors, a rare wood-burning fireplace and a modern kitchen framed by a dramatic floor-to-ceiling bay window. At the rear, a sun-filled, south-facing sunroom with skylights and wall-to-wall glass creates an inviting space to relax. Sliding doors open onto a private deck and garden complete with a storage shed. The second floor offers three well-proportioned bedrooms and a four-piece family bathroom. The south-facing bedroom features built-in shelving and a closet, while the second bedroom offers a window and double closet. The third bedroom, currently configured as a work-from-home office, is distinguished by its charming bay window, decorative fireplace and closet. Ascend to your own private primary retreat, where abundant natural light pours through multiple skylights. An oversized walk-in closet and luxurious six-piece, spa-inspired ensuite create a peaceful escape from the everyday. The lower level adds exceptional versatility, featuring a media room, laundry room and an additional bedroom with its own three-piece ensuite bathroom, ideal for guests, extended family or a private workspace. With its thoughtful updates, inviting outdoor space and coveted Summerhill address, don't miss this opportunity to enjoy stylish, low-maintenance living in one of Toronto's most desirable neighbourhoods, close to the shops, cafés, restaurants, transit and everyday amenities that make Summerhill so special.

107 Macpherson Avenue, Toronto
106 Barton Avenue, Toronto
$2,389,000
8 Beds ⋅ 4 Baths ⋅ C14103808 MLS
This is your chance to create the living space that works for you! 4 Plex, each with 2 bedrooms can be easily converted into two 4 bedroom units or any combination that you desire. Updated 3 +1 two bedrom units.$100,000 + income potential. New furnace-2026, New CAC -2026, basement has been completely water proofed. All you have to do is move-in or lease a portion and have the property carry itself! 7'h basement ceiling. Seller does not warrant retrofit status of units. Walk score at least 93...no car required. Close to TTC, Christie Pitts and all amenities.

106 Barton Avenue, Toronto
84 London Street, Toronto
$1,315,000
3 Beds ⋅ 2 Baths ⋅ C14102270 MLS
Welcome to an exceptional opportunity in one of Toronto's most sought-after areas. Combines character and thoughtful upgrades. Open the door to Wow! High Ceilings, Exposed Z-brick detailing, Guaged slate Floors and Chefs Kitchen. Old Toronto curb appeal with a refreshed low-maintenance front yard and updated facade featuring new wood siding. Inside, original features meet modern style, including original wood floors and railings that have been carefully tightened and refreshed.The upgraded kitchen features higher-end appliances, stylish backsplash, double sink, pot lights, and slate flooring. The dining room offers heated floors with double-door walkout to private, low-maintenance patio retreat, with the cutest little tree you can call your own. Upstairs, is a beautifully updated bathroom with heated floors, a striking tin ceiling, and granite vanity top. The primary bedroom on the third floor showcases an exposed beam ceiling, with nice light coming in from the window and skylights. The second floor has a large bedroom at the front and a small bedroom. More outdoor living with your spacious 13' x 8' north-facing balcony-perfect for a small sectional and morning coffee.The dry, professionally dug and trenched basement features drainage improvements and specialized fabric. A nice basement bathroom with large porcelain tile flooring and giant subway tile. Additional features include storage, cleaned air ducts, soundproofing on the East wall, dedicated A/C units for the upper floors, a newer front roof and a convenient mini shed for garbage bins. It has also had Energy efficient work done by Green Savers. This home offers character, comfort, style and location in one remarkable package. Perfect for a young family, professional couple, investor or even joint ownership, each friend having their own bedroom floor. Unbeatable location. Steps to Bloor Street subway and amenities. Great schools, parks of all sizes and major city attractions. You're going to love living here.

84 London Street, Toronto
33 Tranby Avenue, Toronto
$3,425,000
3 Beds ⋅ 5 Baths ⋅ C14028624 MLS
Welcome to 33 Tranby Avenue - a Walker's Paradise in the heart of the Annex. Steps to Yorkville's shops, restaurants and cafes, U of T, Hospital Row and two subway lines, this transitional residence delivers the highest level of finishings with a warmth that makes it a true home. 2,441 sqft of living space includes 3 bedrooms, 4.5 bathrooms designed for the way professionals and families actually live. A complete renovation by GES Contracting with interiors by Wise Nadel - a fully renovated chef's kitchen, spa-inspired bathrooms, and integrated Sonos sound In Built In Speakers throughout. The garden has been reimagined by AHS Landscaping into a private outdoor sanctuary featuring a gourmet outdoor kitchen, alfresco dining area, and fire pit lounge for cooler evenings. Professional irrigation and architectural outdoor lighting extend the living space into the trees. Lock-and-leave ease meets entertainer's dream - the rare downtown home delivering walkability, design, and outdoor living in one address. Private viewings by appointment. Great Options for parking, whether its street parking or renting near by underground.

33 Tranby Avenue, Toronto
41 Chicora Avenue, Toronto
$2,725,000
5 Beds ⋅ 3 Baths ⋅ C13865362 MLS
Tucked right where Yorkville meets the Annex, this gorgeously renovated Victorian semi is on a quiet, low-traffic street, just a short stroll from all the best of Yorkville. It's got three storeys of that perfect mix of old-house charm and modern-day comfort. You'll notice the soaring ceilings and original details right away, and there's heated flooring throughout the whole lower level and the primary ensuite, so no cold feet in the winter. The kitchen's a real hangout spot, with a gas range and oven, a big centre island, and a wine fridge, and it opens right out onto a landscaped garden terrace with a little fountain. Front and back yards are both nicely landscaped, and there's a gas line already hooked up for the barbecue, so summer entertaining is easy. Upstairs you've got four good-sized bedrooms, a beautiful Victorian-style primary ensuite, and honestly a jaw-dropping third-floor bathroom with a six-piece spa setup, steam shower, and even a Japanese toilet. The wallpaper throughout is imported from Rebel Walls, so it's got that extra designer touch. Walk in the front door and you're greeted by a gorgeous original stained-glass window, and the main floor has a cozy wood-burning fireplace for those nights in. There's also a nice big laundry room on the second floor, which always makes life easier. And the location is unbeatable. You're minutes from Whole Foods, Equinox, the ROM, U of T, and all the shopping and restaurants on Bloor's Mink Mile. Plus you're close to the Financial District, the hospitals, and some of the city's best schools, like Mabin, UCC, The York School, and De La Salle. TTC's just a couple minutes away too.

41 Chicora Avenue, Toronto
140 Bedford Road, Toronto
$6,500,000
4 Beds ⋅ 5 Baths ⋅ C13861584 MLS
A rare, turn-of-the-century Victorian, reimagined for modern luxury in the heart of Annex/Yorkville corridor. Set on one of the area's most coveted streets, this one-of-a-kind detached residence seamless blends timeless old-world charm with elevated contemporary design. Completely rebuilt to the studs with exceptional craftsmanship, this 4+1 bedroom, 5 bathroom home spans over 4,500 sq.ft across three impressive levels. Soaring 10.5 ft ceilings, solid oak and stone floors and curated architectural detailing, create a sense of refined elegance. Gracious principal rooms are designed for both intimate living and sophisticated entertaining, anchored by a stunning marble wood-burning fireplace, one of four fireplaces featured. A custom chef's kitchen serves as the heart of the home, complete with a centre island, Wolf & Subzero appliances, and seamless flow into a formal 10-seat dining room. Just beyond, a private backyard oasis, ideal for hosting or unwinding in style. Natural light pours through expansive windows, enhancing the home's warm, inviting ambiance. The grand staircase leads to the second floor family/media room w/fireplace overlooking the tree-lined street and up to the third level, offering three spacious bedrooms, w/2 full baths. The primary suite is a private retreat, featuring its own fireplace, walk-in closet, secondary laundry & spa-inspired 6 piece ensuite with oversized tub, steam room, and separate shower. Lower level showcases Italian tile, exposed brick, wine room and a generous recreation space with walkout access to a beautifully landscaped backyard complete with in-ground pool & jacuzzi. Set on a 39 x 111 ft lot, the home also offers exceptional curb appeal, heated interlocking drive w/parking for 3 vehicles. Steps to Yorkville's premier shopping and dining, top-tier schools, parks, TTC, and the downtown core, this residence delivers a rare combination of heritage character, modern conformd, and prestigious location - elevated urban living.

140 Bedford Road, Toronto
85 Walmer Road, Toronto
$2,199,000
8 Beds ⋅ 6 Baths ⋅ C13817514 MLS
A five-unit Annex Semi Detached property with the kind of envelope and location that is not being built at today's replacement cost. Legal four-plex above grade plus a legal non-conforming lower suite across 5,225+ sq.ft. on Walmer Road, one of the most tenured income streets in central Toronto. In-place rents sit well below current Annex benchmarks. Income reflects long-tenured tenancies rather than today's market. The unit mix is differentiated - not five interchangeable bachelors. Unit 2 on the main floor is a 1,396 sq.ft. parlour-floor residence with a 21-foot living room, fireplace, oversized kitchen, and a 17-foot principal bedroom. Unit 5 on the third floor (1,171 sq.ft.) is configured with two kitchens, two four-piece baths, two primary bedrooms, an office, and a dining room - lives as one generous suite today. Unit 4 (758 sq.ft.) has a four-piece ensuite, walk-in closet, and living space. Unit 3 (710 sq.ft.) is a full one-bedroom with fireplace, kitchen, and dining. Unit 1 in the lower level (1,191 sq.ft., legal non-conforming) reads as a proper apartment: one-bedroom plus 15-foot den, full kitchen, three-piece bath, and private utility room. Three distinct buyer paths converge here. For the investor, five legal income streams on a single folio, a demand floor set by U of T, downtown professionals, and the Dupont / Spadina subway corridor. For the owner-investor - Multiple units are suitable and are amongst the most substantial owner's suites found inside a purpose-built Annex income property; live in it and let the other four units carry the debt while optionality is preserved. For the long-view buyer planning a single-family reversion - 5,225+ sq. ft. of interior envelope is a credible footprint for a top-of-market Annex restoration, and the existing plumbing stacks, kitchens, and floor plates make either path possible without starting from zero. Walking distance to Bloor Street, Casa Loma, the University of Toronto, and the Spadina subway line.

85 Walmer Road, Toronto
79 Hazelton Avenue, Toronto
$5,995,000
5 Beds ⋅ 5 Baths ⋅ C13812422 MLS
A timeless and elegant Victorian home in Yorkville's best address! A special residence that perfectly blends classic charm with modern convenience. Featuring incredible 10 ft ceilings and gorgeous details - eye catching fireplaces, a stunning staircase, and intricate crown molding and wainscotting. Stately principal rooms with a formal living and dining room, and additional space in the family room. Designer kitchen with elegant finishes, custom cabinetry, a large central island, abundant storage, and French doors leading to the garden. The second floor has two primary suites, each with ensuites and extensive closets. The third floor is absolutely special, with a terrace offering views of Yorkville, a family room, another bedroom, and a full bathroom. An exceptional lower level that maximizes space and functionality: high ceilings, full kitchen, recreation room, bedroom, bathroom, and laundry with a separate entrance. With over 4000 sq ft of living space and superior craftsmanship, this premier property is the pinnacle of the Yorkville lifestyle. The backyard is a private sanctuary in the middle of the city that transcends you to your own peaceful paradise with luscious gardens and a hot tub. The location is exceptional; being just a few steps from Yorkville Ave, and around the corner from the extensive line-up of the finest shops and dining, and all possible urban amenities. All in all, a magnificent house in the finest of locations.

79 Hazelton Avenue, Toronto
107A Scollard Street, Toronto
$2,499,000
4 Beds ⋅ 3 Baths ⋅ C13731184 MLS
A true gem in the heart of Yorkville! Ideally positioned for both residential and commercial use. Currently being used as a single-family home, the main floor living and dining area are open concept with a powder room, galley kitchen and breakfast bar leading to a private back deck and garden. A large and bright full bathroom serves the four bedrooms on the second and third floor. Hardwood and neutral tones throughout provide a clean slate for imagination and creativity. The separate basement can be used as an apartment for additional income or as a space for guests or storage. Literal steps away from luxury retail, dining and hotels, The ROM, Koerner Hall, UofT, N/S/E/W subway connections plus the energy and appeal of one of the city's most coveted neighbourhoods. Zoned for both residential and commercial uses, this perfectly situated blank canvas is your ideal entry point to all that Yorkville has to offer. Check out our virtual tour!

107A Scollard Street, Toronto
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