Annex Homes with 100+ Approx Age

Annex Homes with 100+ Approx Age

Welcome to the Annex, one of Toronto's most vibrant and culturally rich neighborhoods! Nestled just north of downtown, the Annex is a delightful blend of historic charm and modern convenience, making it a sought-after locale for families, professionals, and students alike.

Characterized by its tree-lined streets and stunning Victorian and Edwardian homes, many of which boast an impressive age of 100 years or more, the Annex is a treasure trove for architecture enthusiasts. These beautifully preserved residences reflect the rich history of Toronto while offering a unique aesthetic that stands out in the urban landscape. Imagine living in a home that has stood the test of time, with intricate details and craftsmanship that are hard to find in newer developments.

The neighborhood is not just about beautiful homes; it is also a hub of cultural activity. With its proximity to the University of Toronto, the Annex is alive with a youthful energy and a diverse community. You'll find an array of cafes, boutiques, and bookstores that cater to every taste. Stroll through the streets and discover local art galleries, music venues, and theaters that contribute to the vibrant cultural tapestry of the area.

For those who appreciate nature, the Annex is conveniently located near several parks, offering green spaces for relaxation and recreation. Whether you’re enjoying a leisurely walk in the park or exploring the local shops, the Annex provides a perfect blend of urban living and community spirit.

If you’re looking for a neighborhood rich in history, culture, and charm, the Annex is the perfect place to call home!

Newest Annex Homes with 100+ Approx Age

$1,299,000
3 Beds ⋅ 3 Baths ⋅ C13538050 MLS
Rarely available Prime Seaton Village Semi! This charmingly original family home offers the perfect blend of urban convenience and neighborhood warmth in the heart of The Annex. The property features a 3 fully self-contained suites ideal for rental income or extended-family. Complete with a detached garage and spacious backyard, you are just steps away from the Loblaws, TTC, local shops, parks, and restaurants. All fixtures and chattels are in "as is" condition and property is ready for a full renovation to the buyer's tastes!

636 Clinton Street, Toronto
$1,799,000
6 Beds ⋅ 3 Baths ⋅ C13437452 MLS
27 Hillsboro Avenue Opportunity Meets Lifestyle in the Heart of Avenue & Davenport. Welcome to a rare and versatile offering in one of Toronto's most coveted neighbourhoods. 27 Hillsboro Avenue is a duplex-zoned property with exceptional flexibility for investors, end-users, or visionaries looking to unlock long-term value in this century brick home. The home features a shared driveway with parking for two vehicles a true bonus for this location. All units are vacant, The upper two units have been freshly updated with new flooring, paint, and modern lighting, and are move-in ready or easily rentable. Each upper level enjoys its own private porch, and both feature wood-burning fireplaces, adding warmth and character that tenants and homeowners love.The upper unit also includes a sun porch, offering wonderful bonus family space, a home office, or a cozy reading retreat.The basement in-law suite can be used to provide immediate income from day one. Laundry and utilities are shared, keeping operations straightforward. From a future-planning perspective, the options here are compelling: Keep the current duplex configuration with basement suite,Restore to a stunning single-family home (all stairways are intact),Upgrade or reposition the property to maximize its potential An initial zoning review by Property Pathways indicates potential 6-plex compliance (buyers to confirm independently), making this an exciting prospect for those exploring gentle density and long-term development upside.All of this is wrapped in an unbeatable location: steps to Ramsden Park, minutes to Rosedale subway station, and a short walk to Yorkville, with its world-class dining, shopping, and culture.Live in it. Rent it. Reimagine it. This is a property that grows with your goals-and opportunities like this on Hillsboro Avenue don't come around often. Book your showing and explore the possibilities.

27 Hillsboro Avenue, Toronto
$3,480,000
3 Beds ⋅ 5 Baths ⋅ C13124456 MLS
Welcome to 33 Tranby Avenue - a Walker's Paradise in the heart of the Annex. Steps to Yorkville's shops, restaurants and cafés, 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. 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 firepit 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
$6,500,000
4 Beds ⋅ 5 Baths ⋅ C13047138 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
$7,995,000
6 Beds ⋅ 6 Baths ⋅ C13022438 MLS
Behind the classic facade of 46 Lowther Avenue lies over 6,000 sqft. of beautifully curated living space designed for modern family life in the heart of Yorkville. Every detail has been thoughtfully planned from the open-concept kitchen that anchors the home, to the spacious family room that opens onto a private, estate-like landscaped oasis. The elegant living and dining room offer sophisticated spaces for entertaining, while the home's generous proportions and timeless finishes create an atmosphere of understated luxury. The primary bedroom is a peaceful retreat with a 6-piece spa-inspired ensuite with fireplace and walk-in closet. Two additional bedrooms and a convenient laundry room complete the second floor. The third-floor loft adds flexibility with two more bedrooms, a full bathroom, and ample storage perfect for growing families or guests. The lower level is designed for both comfort and lifestyle, featuring a nanny/bedroom suite with ensuite, wine cellar, lounge, gym, sauna, and abundant storage. Outdoors, the professionally landscaped backyard invites relaxation with multiple decks and lush greenery - a true escape in the city. Situated perfectly on one of Toronto's most desired and admired tree-lined streets, steps from Yorkville's world class shopping, Michelin Starred dining, and top schools, this residence combines elegance, functionality, and the most coveted downtown address.

46 Lowther Avenue, Toronto
$2,324,900
8 Beds ⋅ 6 Baths ⋅ C13021728 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
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