The Annex
About The Annex
One of Toronto’s oldest and most prestigious neighbourhoods, the Annex was a highly-coveted area when it was first constructed in the 1870s. It was almost immediately inhabited by members of the city’s elite—which is to say, those who could afford the gorgeous homes here.
To this day, heritage houses constructed of iconic red brick and stone are still standing in the neighbourhood. These high-quality structures offer visitors and residents a glimpse of Toronto’s past.
The Annex is also very conveniently located. It sits just west of one of Toronto’s most luxurious residential areas (Yorkville) and north of a designer shopping district along Bloor Street West (playfully referred to as “Mink Mile.”)
Who Lives Here
For quite some time, many of the Annex’s mansions were split up into separate apartments as affluent residents moved to newer areas outside the city’s core. For this reason, you’ll find many young people in the area, including students who attend the nearby University of Toronto.
Today, mansions in the Annex are once again being purchased by higher-income individuals—and revamped to suit their lifestyles. Today, you’ll find a great mix of people and cultures, from those who ride bicycles to those who drive Lamborghinis.
What's Great About It?
The convenience of living in the Annex is hard to beat. While many of the neighbourhood’s tree-lined side streets are peaceful and quiet, every corner of the Annex is relatively close to a major intersection or main street. In other words, buzz-worthy boutiques, restaurants, cafes, and bars are never far away.
In particular, this vibrant neighbourhood is known for its eateries, which serve diverse tastes. One of the clear favourites is Kinka Izakaya, a local hotspot for top-notch Japanese cuisine.
When you’re looking to spend a fun afternoon out, consider hitting the shops (BMV Books is a must-visit for lovers of literature) or catching a truly unique film at Bloor Hot Docs. Those looking to stay active will want to visit Niles Nadal JCC, a local community centre featuring a pool, running track, and more.
Lastly, the Annex is much loved by architecture buffs. With so many beautiful streets to explore, you’ll never tire of the gorgeous heritage homes here.
Schools
When it comes to schools in the Annex, the most popular elementary options are Huron Street Junior Public School and Palmerston Junior Public School (both of which are located on their namesake streets).
The Annex is also home to the famed all-boys private school Royal St. George’s College, which welcomes students between Grades 3 to 12.
Homes for sale in The Annex
Looking for listings in The Annex for sale? You’re only seeing some of the listings available here. To see them all, just click the ‘Signup’ or ‘Login’ links below.
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38 Elgin Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12278824
38 Elgin Avenue Toronto M5R 1G6 
$7,390,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12278824
- Bedrooms:
- 3
- Bathrooms:
- 5
Welcome to this truly exceptional, fully renovated residence located in one of Torontos most prestigious neighbourhoods. Just moments from the heart of Yorkville, this home offers the perfect blend of refined design, upscale finishes, and urban convenience.Completely transformed by a professional designer, the interior features a seamless open-concept layout filled with natural light and timeless elegance. The custom kitchen is a true showpiece, featuring high-end appliances, bespoke cabinetry, and a striking marble countertop island perfect for both everyday living and entertaining.Upstairs, youll find spacious bedrooms with custom closets and spa-inspired bathrooms featuring luxurious materials and premium fixtures. The primary suite offers a tranquil escape, complete with a walk-in closet and a beautifully appointed ensuite. Located just steps from Yorkvilles world-class shopping, fine dining, cultural destinations, and transit, this home delivers designer living in one of the citys most desirable locations. Fully Smart Home Control 4 More detailsListed by HOME STANDARDS BRICKSTONE REALTY- Tanya Crepulja
- Keller Williams Real Estate Associates, Brokerage
- 647-293-3785
- tanya@tcteam.ca
- Steven Fontes
- Keller Williams Real Estate Associates, Brokerage
- 416-831-2161
- steve@tcteam.ca
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3 85 Bedford Road in Toronto: Annex Condo Apartment for sale (Toronto C02) : MLS®# C12464029
3 85 Bedford Road Toronto M5R 2K3
$6,980,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12464029
- Bedrooms:
- 3
- Bathrooms:
- 3
A rare fusion of Edwardian heritage and contemporary design by Taylor Hannah Architects, this 2,700 sq. ft. residence at 85 Bedford Road offers house-like scale with condominium ease. Private elevator access opens directly from the underground garage into your own vestibule - no lobby, no corridor delivering unmatched privacy and security. Inside, 10-foot ceilings, radiant heated floors, and a full-span steel frame create expansive, column-free living. The great room flows seamlessly into a dining gallery and chefs kitchen, designed for both intimate evenings and grand entertaining. A dedicated media room provides a second living core, while three full-scale bedrooms offer flexibility for family, guests, or office use. The primary suite is a true retreat, with spa-inspired ensuite and generous proportions that rival a freestanding home. A sculptural metal stair and custom chandelier by THA and Zack Ridgely anchor the historic shell, marrying heritage with artistry. Above, a 480 sq. ft. private rooftop terrace rises above the Annex rooflines, with heated exterior floors extending the season for dining and entertaining. The underground garage - exceptionally rare in Yorkville and the Annex - accommodates 2-3 cars per unit, each with EV charging and water. From your stall, the elevator opens directly into your suite. A full-time property manager, regular maintenance, and daily cleaning of common areas ensure effortless living. Originally an Edwardian Mansion tied to the University of Toronto the structure was rebuilt from triple brick with a full steel frame, lowered four feet to achieve ceiling height and garage access. The result is a boutique residence of only three homes, positioned between two of Yorkville's most prestigious streets. Walkable yet private, historic yet modern, this is a rare opportunity to own a piece of Toronto's architectural legacy reimagined for today. More detailsListed by SOTHEBY'S INTERNATIONAL REALTY CANADA- Tanya Crepulja
- Keller Williams Real Estate Associates, Brokerage
- 647-293-3785
- tanya@tcteam.ca
- Steven Fontes
- Keller Williams Real Estate Associates, Brokerage
- 416-831-2161
- steve@tcteam.ca
-
34 Tranby Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12413517
34 Tranby Avenue Toronto M5R 1N5
$6,399,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12413517
- Bedrooms:
- 4
- Bathrooms:
- 5
Bespoke luxury awaits in this one of a kind Annex/Yorkville masterpiece! This meticulous, back to the brick, custom renovation/rebuild with impressive 3 storey rear addition has been expertly designed and beautifully finished throughout. Extremely rare fully detached, 3 storey, single family home with private heated driveway & built in garage with interior access. Flawless interior design, with in floor radiant heating on all 4 levels, allows natural light to effortlessly cascade throughout the entire living space. Absolutely stunning custom kitchen anchored by show piece La Cornue gas stove with polished brass hardware exhibits timeless style summoning and expression of truly refined taste. Exquisite custom cabinetry meshes perfectly with quartzite counters, matching quartzite backsplash and panelled built appliances. Entertain your family and friends at the centre island offering seamless views of the entire main floor living space and your private backyard. The 2nd floor primary bedroom suite boasts a luxurious 5pc en suite bathroom offering opulent finishes you have come to expect while visiting your favourite spas. The underpinned lower level offers an in home theatre like entertainment space & even interior access to your private built in garage! Escape to your roof top deck amongst the treetops or relax, unwind and truly decompress in your private backyard oasis. Enjoy unmatched luxury in this Ideal location on Tranby Ave, a mature tree lined street ranked as one of Toronto's best by Christopher Hume offering a serene feel with undeniable character. Ideal location is just a short stroll to the boutique shops and cities best restaurants in Yorkville. Or wander and gaze at Toronto's beautiful historical architecture that you can only find in the Annex! 34 Tranby perfectly combines timeless elegance & unmatched luxury accented with just the right amount of historical charm. But to fully appreciate this special home you have to see it for yourself! More detailsListed by FREEMAN REAL ESTATE LTD.- Tanya Crepulja
- Keller Williams Real Estate Associates, Brokerage
- 647-293-3785
- tanya@tcteam.ca
- Steven Fontes
- Keller Williams Real Estate Associates, Brokerage
- 416-831-2161
- steve@tcteam.ca
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173-175 Madison Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12260322
173-175 Madison Avenue Toronto M5R 1V7
$6,199,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12260322
- Bedrooms:
- 14
- Bathrooms:
- 15
Unique Offering, Two-semi detached homes offered together for sale, converted into a 3.5 story 7- plex in the Annex. 1- 3 bedroom unit with 3 washrooms, and 6-2 bedroom units with 2 washrooms, all with ensuite laundry. Hyrdo electricity and gas is all separately metered. Tall ceilings. Combined, the two semis make one of the largest built structures in the Annex. The rear of the property is at the end of the laneway and has 7 car parking. Property is fully rented and is being offered for ~4% cap rate. Benefit from stable rental income or convert into a giant single family home. Heritage property status offers the benefit of lower property tax and financial assistance from the city to maintain the exterior of the building. More detailsListed by RIGHT AT HOME REALTY- Tanya Crepulja
- Keller Williams Real Estate Associates, Brokerage
- 647-293-3785
- tanya@tcteam.ca
- Steven Fontes
- Keller Williams Real Estate Associates, Brokerage
- 416-831-2161
- steve@tcteam.ca
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18 Lowther Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12403548
18 Lowther Avenue Toronto M5R 1C6
$5,495,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12403548
- Bedrooms:
- 4
- Bathrooms:
- 4
Situated on one of the city's most coveted streets, 18 Lowther Avenue blends modern living with timeless elegance. This three bedroom home features an open-concept main floor with over 3,200 sq. feet (above-grade) of light-filled living space throughout. The main floor boasts a large living room with soaring 10 ft ceilings and a spectacular solarium-style window opening up to the private garden patio, perfect for outdoor entertaining. The nice sized dining space flows into a gourmet chef's kitchen with a large island, top-of-the-line appliances, and a beautiful bay window overlooking the streetscape. Ascend the stairs to the second floor, where you will find a generously sized family room that could easily serve as a fourth bedroom. Walk down the hall to the large primary with a five-piece ensuite, lots of closet space, and big windows drawing in a ton of natural light. The third floor has a large bedroom with a walk-in closet, a washroom, a cozy den/office, and a third-floor terrace with north-facing views. The lower level features a third bedroom, washroom, laundry room, and large crawl space perfect for storing seasonal things. Walk out to a private garden oasis and enjoy the convenience of a rare double garage. Just steps from the University of Toronto, the Royal Ontario Museum, and upscale shops and restaurants in Yorkville. Close to some of the city's best schools, galleries, and green spaces. More detailsListed by ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM- Tanya Crepulja
- Keller Williams Real Estate Associates, Brokerage
- 647-293-3785
- tanya@tcteam.ca
- Steven Fontes
- Keller Williams Real Estate Associates, Brokerage
- 416-831-2161
- steve@tcteam.ca
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403 10 Prince Arthur Avenue in Toronto: Annex Condo Townhouse for sale (Toronto C02) : MLS®# C12417299
403 10 Prince Arthur Avenue Toronto M5R 1A9
$5,490,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12417299
- Bedrooms:
- 3
- Bathrooms:
- 2
Discover urban sophistication at its finest in this stunning two-bedroom, two-bathroom condo within an exclusive boutique building of just 25 residences. This brand-new home offers an impressive 2,400 square feet of interior living space with soaring 10-foot ceilings that create an airy, open atmosphere throughout. The heart of this residence features an expansive gourmet kitchen equipped with premium Wolf and Sub-Zero appliances, perfect for culinary enthusiasts and entertaining alike. Step out onto either of two private balconies one accessible from the family room and another from the primary bedroom to enjoy your morning coffee or evening relaxation. Located in the coveted Annex neighborhood, you'll be mere steps from Whole Foods Market for convenient grocery shopping and the St George transit station for seamless city connectivity. The area boasts proximity to the University of Toronto, world-class Yorkville dining establishments, and cultural attractions that define Toronto's sophisticated urban lifestyle. Building amenities elevate daily living with 24-hour concierge service, valet parking, a private fitness facility, and an elegant resident dining lounge complete with catering kitchen. Your purchase includes secure underground parking for two vehicles plus additional storage space.The tranquil greenery of nearby parks, including Frank Stollery Parkette, provides a peaceful escape from city energy while maintaining easy access to exceptional shopping and dining.Quality construction meets thoughtful design in this rare opportunity to own a piece of Toronto's most desirable neighborhood, where urban convenience harmoniously blends with residential charm. More detailsListed by PROPERTY.CA INC.- Tanya Crepulja
- Keller Williams Real Estate Associates, Brokerage
- 647-293-3785
- tanya@tcteam.ca
- Steven Fontes
- Keller Williams Real Estate Associates, Brokerage
- 416-831-2161
- steve@tcteam.ca
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40 Bernard Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12435486
40 Bernard Avenue Toronto M5R 1R2
$4,998,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12435486
- Bedrooms:
- 5
- Bathrooms:
- 5
40 Bernard, with its recently completed and back to the bricks restoration/renovation, is one of the most beautiful homes in the East Annex. This historic Victorian is located on the best block of Bernard; just steps to Yorkville and Bloor Street shops and transit. Boasting 3685 square feet with tall ceilings throughout, this house is wonderfully spacious and airy. It retains its charm blended seamlessly with contemporary style in an artfully designed package. The main floor is open concept with a living room, dining room, and chef's kitchen with professional appliances, dining banquette, custom rift oak and white cabinetry, gorgeous fluted oak on the oversized island and coffee pantry and ribbed glass lit china cabinet. The leathered quartzite counter and backsplash is unique, durable and a natural piece of art. The kitchen is bathed in light with a lovely bank of side windows and an oversized sliding door leading to the private garden. The stunning primary retreat features a generous sized walk-in closet, elegant wainscotting and Juliet balcony. The ensuite washroom is encased in gorgeous tile with custom walnut vanity, matte resin freestanding tub and separate water closet. The third floor has been expanded to create two generous bedrooms and three piece washroom. The dug out lower level with 8' ceilings maintains the graciousness of the rest of the home with custom built ins, recreation room, bedroom, laundry and three piece washroom. A deep and private garden with deck and patio are enjoyed off the main floor. The library walks out to a balcony with lovely views over Bernard Avenue, and the third floor sundeck is secluded in the trees. High quality materials have been incorporated throughout with new mechanical systems. This home truly offers it all! More detailsListed by ROYAL LEPAGE/J & D DIVISION- Tanya Crepulja
- Keller Williams Real Estate Associates, Brokerage
- 647-293-3785
- tanya@tcteam.ca
- Steven Fontes
- Keller Williams Real Estate Associates, Brokerage
- 416-831-2161
- steve@tcteam.ca
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1202 206 Bloor Street W in Toronto: Annex Condo Apartment for sale (Toronto C02) : MLS®# C12387811
1202 206 Bloor Street W Toronto M5S 1T8
$4,995,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12387811
- Bedrooms:
- 3
- Bathrooms:
- 3
Sophisticated Luxury in the Heart of Yorkville. Welcome to Museum House, an iconic 19-storey landmark residence in the heart of Bloor-Yorkville, offering boutique luxury living at its finest. This breathtaking 3-bedroom, 3-bathroom suite spans over 2,500 square feet of elegantly appointed space, with direct elevator access opening into your private residence. Enjoy uninterrupted southern CN Tower city views, each room framed by floor-to-ceiling windows that flood the home with natural light. The expansive open-concept living and dining areas are perfect for entertaining, while the custom kitchen boasts a large island, premium appliances, integrated wine refrigeration, and a sunlit breakfast area. The primary suite is a true retreat, featuring a spa-inspired ensuite and a spacious walk-in closet. The versatile third bedroom easily transforms into a refined home office. With soaring ceilings, impeccable finishes, and an unmatched location steps from Yorkville's finest restaurants, designer boutiques, art galleries, and cultural institutions - this is urban luxury redefined. More detailsListed by HARVEY KALLES REAL ESTATE LTD.- Tanya Crepulja
- Keller Williams Real Estate Associates, Brokerage
- 647-293-3785
- tanya@tcteam.ca
- Steven Fontes
- Keller Williams Real Estate Associates, Brokerage
- 416-831-2161
- steve@tcteam.ca
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41 Boswell Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12280447
41 Boswell Avenue Toronto M5R 1M5
$4,995,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12280447
- Bedrooms:
- 4
- Bathrooms:
- 5
Beautifully crafted 3+1 bedroom detached home located in the heart of Yorkville. This stunning property features a quartzite kitchen, a lower-level gym with full-height ceilings, and premium finishes throughout. The interior design blends white oak, quartzite, marble, and brass accents, all meticulously curated during a complete renovation. Tucked away on a quiet cul-de-sac, this home offers a perfect alternative to condo living, combining luxury, style, and comfort. Heated driveway and pathways add both practicality and charm to this remarkable residence. A true Yorkville masterpiece, it delivers a refined yet functional living space that defines modern sophistication. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- Tanya Crepulja
- Keller Williams Real Estate Associates, Brokerage
- 647-293-3785
- tanya@tcteam.ca
- Steven Fontes
- Keller Williams Real Estate Associates, Brokerage
- 416-831-2161
- steve@tcteam.ca
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37 Madison Avenue in Toronto: Annex Commercial for sale (Toronto C02) : MLS®# C12254763
37 Madison Avenue Toronto M5R 2S2
$4,988,888 /For SaleCommercial- Status:
- Active
- MLS® Num:
- C12254763
- Total Area:
- 7,262 sq. ft.
Offered at $4,988,888, 37 Madison Avenue is a rare opportunity to own a landmark building in the heart of Toronto's prestigious Annex/Yorkville corridor. Designed by Edward James Lennox, architect of Casa Loma and Old City Hall, this three-storey, approx. 6,000 sq. ft. property blends Gothic, Queen Anne, and Edwardian influences with exceptional presence. Currently configured as elegant office space with 12 executive offices, 4 bathrooms, and 8 rear parking spaces, the building offers outstanding flexibility for a head office, wellness clinic, gallery, boutique hotel, or studio. A striking façade, historic character, and prime location just steps from Bloor Street, two subway lines, U of T, and Yorkville make this a truly unique commercial offering. More detailsListed by RE/MAX REALTRON REALTY INC.- Tanya Crepulja
- Keller Williams Real Estate Associates, Brokerage
- 647-293-3785
- tanya@tcteam.ca
- Steven Fontes
- Keller Williams Real Estate Associates, Brokerage
- 416-831-2161
- steve@tcteam.ca
-
37 Madison Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12259630
37 Madison Avenue Toronto M5R 2S2
$4,988,888Residential Freehold- Status:
- Active
- MLS® Num:
- C12259630
- Bedrooms:
- 1
- Bathrooms:
- 4
Step into history at 37 Madison Avenue, an architectural masterpiece by Edward James Lennox, famed for landmarks like Casa Loma and Old City Hall. Completed in 1891, this rare heritage home blends Gothic, Romantic Revival, Queen Anne, and Edwardian influences with striking presence and timeless elegance. Located between Yorkville and the Annex, the home features a distinctive façade, soaring ceilings, original woodwork, and expansive windows throughout approx. 6,000 sq. ft. of living space. A unique opportunity to restore or reimagine a landmark residence in one of Toronto's most coveted neighbourhoods. Enjoy unmatched access to world-class dining, boutique shopping, cultural institutions, top schools, and two subway lines, all just steps from your front door More detailsListed by RE/MAX REALTRON REALTY INC.- Tanya Crepulja
- Keller Williams Real Estate Associates, Brokerage
- 647-293-3785
- tanya@tcteam.ca
- Steven Fontes
- Keller Williams Real Estate Associates, Brokerage
- 416-831-2161
- steve@tcteam.ca
-
700 38 Avenue Road in Toronto: Annex Condo Apartment for sale (Toronto C02) : MLS®# C12210832
700 38 Avenue Road Toronto M5R 2G2
$4,980,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12210832
- Bedrooms:
- 3
- Bathrooms:
- 4
Enjoy the luxury of living in The Prince Arthur at a prime Yorkville location. Along with providing valet parking, the attentive 24-hour concierge and valets create a sense of secure privacy as they manage access to condo areas. Situated in the south tower, this corner suite has a wonderful layout featuring 3 bedrooms in two wings with 4 bathrooms, 2 balconies, 3 parking spaces, 2 lockers and many built-ins. The suite is approximately 3115 square feet, with desirable western views, peaceful northern views from the primary bedroom and tandem sitting room suite and additional south views in the kitchen and dining room. Enter through wide double doors to an inviting foyer with a large closet, continuing into the large welcoming living room, the focus of the suite. As you enter, you find an elegant, wood paneled library through double doors on the right. On the left a second set of double doors leads to a separate, formal dining room which is also accessible from a beautiful modern kitchen with thoughtful design and eat-in area. The northern wing features a primary bedroom with a relaxing tandem sitting room, ensuite bathroom plus his and her closets. This wing includes a second bedroom, ensuite and sitting/office area with a walk-out to a west-facing balcony. The third/guest bedroom and ensuite are in the south wing next to the kitchen and powder room. Marvelous amenities include an exercise room, two well appointed party rooms each with open balconies (one overlooking Yorkville), sauna, theatre and library. Generous ensuite laundry area with laundry sink. Embrace the adventure and excitement of living in the cultural heart of Toronto. More detailsListed by SUTTON GROUP OLD MILL REALTY INC.- Tanya Crepulja
- Keller Williams Real Estate Associates, Brokerage
- 647-293-3785
- tanya@tcteam.ca
- Steven Fontes
- Keller Williams Real Estate Associates, Brokerage
- 416-831-2161
- steve@tcteam.ca
Data was last updated October 16, 2025 at 12:15 AM (UTC)
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