Annex Homes with 100+ Approx Age

Welcome to 87 Olive Ave., a beautifully maintained 3+1 bedroom, 2 bath semi-detached home in the heart of Seaton Village in the Annex. Set on a quiet, tree-lined street, this is a home that truly invites you to settle in, grow and enjoy city living at its best. Here, the charm and community of a family-friendly neighbourhood are paired with the energy and convenience of Bloor Street and downtown just minutes away. A welcoming front porch offers the perfect spot for morning coffee, an evening glass of wine or a friendly chat with neighbours. Inside, the airy open-concept main floor features high ceilings, hardwood floors and pot lights throughout. The inviting living room is anchored by a working gas fireplace, adding warmth and a cozy glow to chilly winter evenings. The modern renovated kitchen opens to a raised deck and large, fully fenced backyard - great for summer BBQs and entertaining. Plenty of room for playtime, gardening, outdoor dining or simply relaxing under the trees. Weber gas BBQ included! The bright and spacious finished basement is a standout feature. This is genuine additional living space, complete with a 4th bedroom and 3-piece bathroom! Use it as a rec room, home office, gym, guest suite or a combination of whatever your lifestyle calls for. Freshly painted throughout, including the porch and deck, with upgraded light fixtures in every room, this lovingly cared-for home is truly move-in ready. Steps to Vermont Square Park, St. Alban's Boys & Girls Club (preschool, swimming pool), Bill Bolton Skating Arena, and Palmerston Avenue Junior Public School (w/ French Immersion). Christie Pits, Bathurst Subway Station, Loblaws, Summerhill Market, Fiesta Farms, and Farm Boy all close by too! A special home in a special neighbourhood. Come experience it for yourself! Open House Sat/Sun 2-4pm.

87 Olive Avenue, 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

$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

$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

$1,599,000

2 Beds ⋅ 2 Baths ⋅ C13719218 MLS

Welcome to this beautifully maintained property ideally situated at Davenport & Dupont, in the sought-after Yorkville Annex neighbourhood. Offering 4 spacious offices/rooms and 2 bathrooms, plus a fully finished basement, this fully serviced property is move-in ready for a wide range of business uses. Zoned EL, this rare and coveted designation allows exceptional flexibility for owner-users and investors alike, supporting a wide variety of commercial and institutional applications. Whether you're looking to establish a professional office, a boutique service business, or another EL-permitted use, this property delivers the versatility today's buyers demand. Enjoy a private, walk-out rear-facing balcony - a rare outdoor retreat in this vibrant, walkable pocket of the city. Just steps from the eclectic shops, cafés, and restaurants that make the Annex and Yorkville area so desirable, this location offers unbeatable convenience for staff, clients, and visitors. Adding to the long-term upside, the property sits directly adjacent to the upcoming ANX development - a major project set to bring endless foot traffic and increased visibility to the area for years to come. This is a fantastic opportunity to secure a well-located commercial property in one of the city's most established and continually evolving neighbourhoods.

348 Dupont Street, Toronto

$1,599,000

2 Baths ⋅ C13704862 MLS

Welcome to this beautifully maintained property ideally situated at Davenport & Dupont, in the sought-after Yorkville Annex neighbourhood. Offering 4 spacious offices/rooms and 2 bathrooms, plus a fully finished basement, this fully serviced property is move-in ready for a wide range of business uses. Zoned EL, this rare and coveted designation allows exceptional flexibility for owner-users and investors alike, supporting a wide variety of commercial and institutional applications. Whether you're looking to establish a professional office, a boutique service business, or another EL-permitted use, this property delivers the versatility today's buyers demand. Enjoy a private, walk-out rear-facing balcony - a rare outdoor retreat in this vibrant, walkable pocket of the city. Just steps from the eclectic shops, cafés, and restaurants that make the Annex and Yorkville area so desirable, this location offers unbeatable convenience for staff, clients, and visitors. Adding to the long-term upside, the property sits directly adjacent to the upcoming ANX development - a major project set to bring endless foot traffic and increased visibility to the area for years to come. This is a fantastic opportunity to secure a well-located commercial property in one of the city's most established and continually evolving neighbourhoods.

348 Dupont Street, Toronto

$1

7 Baths ⋅ C13614320 MLS

Colliers Private Capital Investment Group is pleased to present 34 Madison Avenue, an 8,048 SF purpose-built childcare facility situated in The Annex, one of Toronto's most affluent and highly sought-after neighbourhoods. The Property is leased to a well-established Toronto-based childcare operator on a 10-year initial term, providing a secure and growing income stream with minimal landlord responsibilities. The Property benefits from a 98-child licensed capacity and has undergone a comprehensive renovation, including structural improvements, handicapped washrooms, sprinkler installation, new lighting, electrical and HVAC systems, plumbing upgrades, washroom additions, and the conversion of the former parking area into an outdoor play space. Situated on a 6,340 SF lot with 50 feet of frontage along Madison Avenue, the property is steps from Bloor Street West, the University of Toronto, and Spadina subway station. With a strong demand-supply imbalance, significant barriers to new childcare facility development, a defensive income profile and long-term cash flow with annual escalations, 34 Madison Avenue represents a rare opportunity to acquire a stabilized, single-tenant asset with contractual rental growth in a premier downtown location.

34 Madison Avenue, Toronto

$1

7 Baths ⋅ C13614310 MLS

Colliers Private Capital Investment Group is pleased to present 34 Madison Avenue, an 8,048 SF purpose-built childcare facility situated in The Annex, one of Toronto's most affluent and highly sought-after neighbourhoods. The Property is leased to a well-established Toronto-based childcare operator on a 10-year initial term, providing a secure and growing income stream with minimal landlord responsibilities. The Property benefits from a 98-child licensed capacity and has undergone a comprehensive renovation, including structural improvements, handicapped washrooms, sprinkler installation, new lighting, electrical and HVAC systems, plumbing upgrades, washroom additions, and the conversion of the former parking area into an outdoor play space. Situated on a 6,340 SF lot with 50 feet of frontage along Madison Avenue, the property is steps from Bloor Street West, the University of Toronto, and Spadina subway station. With a strong demand-supply imbalance, significant barriers to new childcare facility development, a defensive income profile and long-term cash flow with annual escalations, 34 Madison Avenue represents a rare opportunity to acquire a stabilized, single-tenant asset with contractual rental growth in a premier downtown location.

34 Madison Avenue, Toronto

$1,199,000

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

$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

Annex Homes with 100+ Approx Age

Newest Annex Homes with 100+ Approx Age