
The Annex
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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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1-6 66 Avenue Road in Toronto: Annex Commercial for sale (Toronto C02) : MLS®# C12002469
1-6 66 Avenue Road Annex Toronto M5R 3N8 $7,500,000 /For SaleCommercial- Status:
- Active
- MLS® Num:
- C12002469
- Major Bus.:
- Medical/Dental
- Total Area:
- 0 sq. ft.0 m2
Once-in-a-lifetime investment opportunity. Prime Yorkville medical offices. Location does not get better than this. On the corner of Lowther/Avenue. Six fully tenanted commercial offices/medical offices. Complete first floor with auxiliary storage room in lower level. 12 underground parking spots. 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
-
38 Elgin Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12278824
38 Elgin Avenue Annex 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
-
Garden Home 2 10 Prince Arthur Avenue in Toronto: Annex Condo Apartment for sale (Toronto C02) : MLS®# C12243593
Garden Home 2 10 Prince Arthur Avenue Annex Toronto M5R 1A9 $6,950,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12243593
- Bedrooms:
- 4
- Bathrooms:
- 3
An exceptional Garden Home now available at 10 Prince Arthur! The style and convenience of an Urban Bungalow - with almost 2,750 square feet of gracious interior space on a single level, surrounded by a private landscaped garden terrace all to yourself! Unequalled space steps to Avenue Road and Bloor in an intimate development of just 25 residences. 11 foot ceilings, expansive kitchen featuring Wolf and Sub-Zero appliances, 2 bedrooms with a den and office... this really feels like home. Developed by North Drive and designed by Richard Wengle with refined interiors from Brian Gluckstein and Michael London and featuring a very limited number of residences in a truly boutique building. Enjoy the comfort and convenience of 24-hour concierge, valet parking, private fitness facility, resident dining lounge with catering kitchen and courtyard sculpture garden designed by Janet Rosenberg. Located in the Annex, just steps from exceptional shopping, Yorkville's world-class dining, U of T, cultural institutions and the tranquil greenery of nearby parks, 10 Prince Arthur presents a rare blend of urban sophistication and neighborhood charm. **EXTRAS** A unique urban home. Wrap around garden with 3 distinct areas and 5 walk-outs from inside. Landscape lighting and irrigation. Includes secure, 2 car underground parking, storage and hst. 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
-
Part of 128 Pears Avenue in Toronto: Annex Commercial for sale (Toronto C02) : MLS®# C12023590
Part of 128 Pears Avenue Annex Toronto M5R 1T2 $6,723,000 /For SaleCommercial- Status:
- Active
- MLS® Num:
- C12023590
- Major Bus.:
- Retail Store Related
- Total Area:
- 4,482 sq. ft.416 m2
3-storey luxury freehold commercial component with ground-floor lobby, steps from busy intersection of Avenue Rd and Davenport Rd. Close proximity to Yorkville and to Rosedale Subway Station. Ideal for a wide range of uses including office, medical, and commercial uses. Shared access to elevator pursuant to Facilities Agreement. More detailsListed by THE BEHAR GROUP 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
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173-175 Madison Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12260322
173-175 Madison Avenue Annex 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
-
404 10 Prince Arthur Avenue in Toronto: Annex Condo Apartment for sale (Toronto C02) : MLS®# C12241419
404 10 Prince Arthur Avenue Annex Toronto M5R 1A9 $5,590,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12241419
- Bedrooms:
- 3
- Bathrooms:
- 3
Now available at 10 Prince Arthur! This brand new 2 bedroom plus family room residence represents one of the final homes at this intimate development of just 25 residences. With occupancy already underway, now is the ideal time to secure this elegant suite providing almost 2,400 square feet of interior space with 10 foot ceilings, an expansive kitchen featuring Wolf and Sub-Zero appliances and a privileged south exposure with views over quiet Prince Arthur Avenue. Developed by North Drive and designed by Richard Wengle with refined interiors from Brian Gluckstein and Michael London and featuring a very limited number of residences in a truly boutique building. Enjoy the comfort and convenience of 24-hour concierge, valet parking, private fitness facility, resident dining lounge with catering kitchen and courtyard sculpture garden designed by Janet Rosenberg. Located in the Annex, just steps from exceptional shopping, Yorkville's world-class dining, U of T, cultural institutions and the tranquil greenery of nearby parks, 10 Prince Arthur presents a rare blend of urban sophistication and neighborhood charm. **EXTRAS** A unique urban home. 2 balconies, one from family room and one from primary bedroom. Includes secure, 2 car underground parking, storage and hst. 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
-
41 Boswell Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12280447
41 Boswell Avenue Annex Toronto M5R 1M5 $5,250,000Residential 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
-
90 Madison Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12269858
90 Madison Avenue Annex Toronto M5R 2S4 $4,999,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12269858
- Bedrooms:
- 7
- Bathrooms:
- 8
Architectural Masterpiece Of Urban Design On One Of The Most Coveted Streets, In The Heart Of The Annex. Located On A Large 40 x 127 West Facing Lot, On A Premium Block. Retaining Its Turn Of The Century Character This Home Was Rebuilt To Reflect Modern Design And Traditional Warmth. A Spectacular Over 3700 sf New York Style Loft Was Seamlessly Added To A Traditional Annex Home Creating Approximately 7000 sf Living Space. This Lightfilled contemporary space with its soaring 3 storey west facing windows brings the outside into the inside of the home, and features fabulous Catwalks Connecting The 3 Levels And Spaces. An Elevator From The Lower Level Garage Connects The 4 Levels. The Space Is Open Yet There Is Privacy In The 4 Bedrooms. A Fabulous 2 Bedroom 2250 sf Separate Unit With a Walkout Lower Level Plus A 2 Bedroom Third Floor Unit Allow For Extra Income Or Extended Family Space. 4 - 5 Car Parking, Private Drive, Built In Garage. Exceptional Urban Living, Just Steps To Yorkville, Subway, Royal St Georges College, Huron Public, Mabin School, Rosedale Day School, UTS, U of T More detailsListed by RE/MAX PROFESSIONALS 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
-
1202 206 Bloor Street W in Toronto: Annex Condo Apartment for sale (Toronto C02) : MLS®# C12243091
1202 206 Bloor Street W Annex Toronto M5S 1T8 $4,995,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12243091
- 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 Yorkvilles 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
-
37 Madison Avenue in Toronto: Annex Commercial for sale (Toronto C02) : MLS®# C12254763
37 Madison Avenue Annex Toronto M5R 2S2 $4,988,888 /For SaleCommercial- Status:
- Active
- MLS® Num:
- C12254763
- Total Area:
- 7,262 sq. ft.675 m2
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 Annex 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 Annex 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

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