
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
-
34 Tranby Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12042873
34 Tranby Avenue Annex Toronto M5R 1N5 $6,879,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12042873
- 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, gym/yoga room & 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 Torontos 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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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
-
90 Madison Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12051367
90 Madison Avenue Annex Toronto M5R 2S4 $5,859,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12051367
- 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
-
43 Bernard Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C11047417
43 Bernard Avenue Annex Toronto M5R 1R3 $5,845,000Residential Freehold- Status:
- Active
- MLS® Num:
- C11047417
- Bedrooms:
- 4
- Bathrooms:
- 5
Rare single family detached house on south side of the street in East Annex neighbourhood This Exquisite Luxury Home Is Nestled On Prime Yorkville Street, in The Heart of one of Toronto's Most Prestigious Neighbourhoods With Over 4000 Sq Ft of Living Space. Designed with Entertaining in Mind, the Main Floor Offers a Large Kitchen, Living and Dining Room with a Walkout to a Backyard Oasis, Featuring a Hot Tub and A Koi Pond Creating A Serene Atmosphere. Featuring High Ceilings Throughout, An Impressive Primary Suite, Two Private Exterior Spaces, and Lounge. Conveniently Located Steps Away From The City's Best Shopping, Restaurants, And All Toronto Has To Offer. **EXTRAS** Two Furnaces (One New) and Two New Air Conditioners, New Tankless Water Heater. Seller to provide a limited one year warranty on all HVAC, Electrical, Plumbing, Foundation, and Roof. Parking Pad can accommodate 2 cars but is 1 legal spot 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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3201 1 Bedford Road in Toronto: Annex Condo Apartment for sale (Toronto C02) : MLS®# C12110827
3201 1 Bedford Road Annex Toronto M5R 2B5 $5,800,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12110827
- Bedrooms:
- 3
- Bathrooms:
- 3
Welcome to Suite 3201 at One Bedford a rare penthouse residence in one of Toronto's most prestigious addresses. This exclusive 3-bedroom, 3-bathroom home spans 2,465 square feet and is one of only two suites on the floor, offering exceptional privacy and panoramic views of the CN Tower, downtown skyline, and lake. Impeccably upgraded with designer finishes, the suite features hardwood floors, custom pot lighting, tailored wallpaper, and elegant fixtures throughout. A spacious foyer leads into a stunning living room with floor-to-ceiling windows and a formal dining space beneath a sculptural chandelier. The chefs kitchen is a true showpiece, with a quartz waterfall island, glass tile backsplash, Miele appliances, and bespoke cabinetry. The primary suite is a private retreat, complete with its own balcony, a walk-in closet, and a spa-like ensuite with a deep soaker tub beneath a picture window, double vanity, marble tile, and separate water closet. The second bedroom features east-facing windows, custom built-ins, and a sleek 3-piece ensuite. The third bedroom with balcony access adds flexibility as a home office, library, family room or bedroom. Even the laundry room has been thoughtfully designed with custom cabinetry, quartz counters, and full-size washer/dryer. Includes two premium side-by-side parking spots and a private locker. Residents enjoy five-star amenities: indoor pool, hot tub, sauna, steam room, fitness centre, party room, outdoor terrace, concierge, guest suites, and more. Unbeatable location near U of T, ROM, Royal Conservatory, and Yorkville's finest shops and dining. This is elevated, turnkey penthouse living refined, private, and move-in ready. This suite includes 2 premium side-by-side parking spots & a private locker rare in the city. 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
-
404 10 Prince Arthur Avenue in Toronto: Annex Condo Apartment for sale (Toronto C02) : MLS®# C11935021
404 10 Prince Arthur Avenue Annex Toronto M5R 1A9 $5,590,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C11935021
- Bedrooms:
- 3
- Bathrooms:
- 3
This elegant 2 bedroom plus family room residence represents one of the final homes at the upcoming 10 Prince Arthur. With occupancy anticipated this summer, now is the ideal time to secure this distinctive 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. Construction nearing completion with occupancy expected this summer. 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
-
37 Madison Avenue in Toronto: Annex Commercial for sale (Toronto C02) : MLS®# C9416439
37 Madison Avenue Annex Toronto M5R 2S2 $5,500,000 /For SaleCommercial- Status:
- Active
- MLS® Num:
- C9416439
- Total Area:
- 7,262 sq. ft.675 m2
Step into history with this extraordinary property, designed by the visionary architect Edward James Lennox, renowned for his eclectic style that blends Gothic, Romantic Revival, Queen Anne, and Edwardian features. This unique building, originally completed in 1891 as the private residence of esteemed house builder Lewis Lukes, is located between the desirable Annex and Yorkville neighborhoods. Currently utilized as commercial office space, this stunning three-storey building spans approximately 6,000 sq. ft. and offers 12 executive offices, four bathrooms, and eight valuable parking spots at the rear. Rare find in this vibrant area.The exterior is an architectural delight, showcasing Lennox's signature design elements, while the interior maintains a perfect balance of historic charm and modern functionality. This property is ideal for businesses looking to establish themselves in a prestigious location. Perfect for a head office, medical office, gallery, boutique hotel or spa. 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®# C9416378
37 Madison Avenue Annex Toronto M5R 2S2 $5,500,000Residential Freehold- Status:
- Active
- MLS® Num:
- C9416378
- Bedrooms:
- 1
- Bathrooms:
- 4
Step into history with this extraordinary architectural masterpiece, designed by visionary Edward James Lennox, renowned for his eclectic style that seamlessly blends Gothic, Romantic Revival, Queen Anne, and Edwardian influences. Originally completed in 1891 as the private residence of esteemed house builder Lewis Lukes, this one-of-a-kind home offers a rare opportunity to own a piece of Toronto's architectural heritage.Located between the vibrant Yorkville neighborhood and the prestigious Annex, this property places you in the heart of two of Toronto's most desirable areas. The homes distinctive facade and intricate detailing are a testament to Lennox's unmatched craftsmanship, while the interiors feature soaring ceilings, expansive windows, and original woodwork, creating a sense of timeless elegance.With easy access to world-class dining, upscale shopping, cultural institutions, and parks, this property is perfectly positioned for those who appreciate both history and modern urban living. A once-in-a-lifetime opportunity to own an iconic piece of Toronto's past in an unbeatable location. 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
-
41 Boswell Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C11923117
41 Boswell Avenue Annex Toronto M5R 1M5 OPEN HOUSE: May 13, 202511:30 AM - 01:00 PM EDTOpen House on Tuesday, May 13, 2025 11:30AM - 1:00PMOPEN HOUSE: May 17, 202502:00 PM - 04:00 PM EDTOpen House on Saturday, May 17, 2025 2:00PM - 4:00PM$5,500,000Residential Freehold- Status:
- Active
- MLS® Num:
- C11923117
- 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
-
102 277 Davenport Road in Toronto: Annex Commercial for sale (Toronto C02) : MLS®# C12022688
102 277 Davenport Road Annex Toronto M5R 1J9 $5,198,000 /For SaleCommercial- Status:
- Active
- MLS® Num:
- C12022688
- Total Area:
- 3,663 sq. ft.340 m2
One of the sexiest commercial spaces you will ever see. This architectural gem designed by Hariri Pontarini, 277 Davenport Rd is one of Yorkville's most desirable boutique luxury condominiums. Steps to the heart of Yorkville, Suite 102 delivers just shy of 3,700 sq. ft. of exquisite space, from the beautifully proportioned reception area to the open concept main floor with beautiful tall ceilings and dramatic double height ceiling draws the eye skyward towards the beautiful mezzanine level. Exeptional office/retail space zoned CR 2.0 for a variety of uses. Prime location, steps to the heart of Yorkville with superb exposure on Davenport between Bedford & Avenue Road. 2 Car parking, polished concrete floors, wheelchair accessible with ramp, 3 x 2 piece baths, ensuite laundry. 5 Minute walk to Dupont & Bay St. subway stations. More detailsListed by SOTHEBY`S INTERNATIONAL REALTY CANADA and 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
-
366 Bloor Street W in Toronto: Annex Commercial for sale (Toronto C02) : MLS®# C11962599
366 Bloor Street W Annex Toronto M5S 1X2 $4,788,000 /For SaleCommercial- Status:
- Active
- MLS® Num:
- C11962599
- Total Area:
- 3,884 sq. ft.361 m2
Prime Bloor Street location. 40 meters to Spadina Subway Station. Vendor will leaseback the existing restaurant. All restaurant chattels, fixtures and equipment will remain the property of the Vendor. 2 x 1,200 sf. x 2 bedroom and 2 washroom, newly finished apartments will be vacant on closing. Apartments are furnished. Market rents for each apartment are at $5,500 per month. Apartments each have their own private roof-top terraces. Please download property offering memorandum. More detailsListed by CAPITAL NORTH REALTY CORPORATION- 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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