
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
-
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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18 Lowther Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12223307
18 Lowther Avenue Annex Toronto M5R 1C6 $5,895,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12223307
- 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 featuring 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 with spectacular solarium-style window opening up to the private garden patio, perfect for outdoor entertaining. The nice sized dining space flows in a gourmet chef's kitchen with 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 generous sized family room that could easily serve as a fourth bedroom. Walk down the hall to the large primary with 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 walk-in closet, washroom, 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
-
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 $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
-
90 Madison Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12051367
90 Madison Avenue Annex Toronto M5R 2S4 $5,369,490Residential 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
-
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
-
79 Kendal Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12160750
79 Kendal Avenue Annex Toronto M5R 1L8 $5,195,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12160750
- Bedrooms:
- 4
- Bathrooms:
- 6
Contemporary brownstone in the heart of the Annex! This newly constructed home blends in beautifully within the neighborhood while offering every modern convenience, extraordinary design and an optimal layout. Ideal for everyday living and entertaining! Stunning hardwood floors, soaring ceilings and gorgeous views are the backdrop to this oversized urban oasis. Fabulous main floor layout with the perfect balance of open concept spaces and sophisticated division. Top of the line appliances and millwork. Spacious bedrooms with dreamy ensuites and extensive closet space. Large second floor laundry room! Absolutely spectacular lower level with unbelievable ceiling height and direct access from the garage. Heated driveway! Large rear yard with ample space and great privacy. Top notch location within steps to the park, Bloor St, Dupont St, Bathurst Street, Yorkville. Within the catchment for Huron Public School and close to private schools such as Royal St. George's, Bishop Strachan School, The Mabin School and Upper Canada College. Steps to public transport, and countless top tier restaurants, cafes, shops and galleries. 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
-
3201 1 Bedford Road in Toronto: Annex Condo Apartment for sale (Toronto C02) : MLS®# C12158844
3201 1 Bedford Road Annex Toronto M5R 2B5 $4,999,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12158844
- 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 2+1 bed,3-bath home spans 2,539 sq. ft. 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 chef's 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. A spacious den with balcony access adds flexibility as a home office or third 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. Five-star amenities incl. indoor pool, hot tub, gym, concierge, guest suites, visitor parking & more for elevated urban living. 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
-
1202 206 Bloor Street W in Toronto: Annex Condo Apartment for sale (Toronto C02) : MLS®# C12234249
1202 206 Bloor Street W Annex Toronto M5S 1T8 $4,995,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12234249
- 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
-
133 Pears Avenue in Toronto: Annex Condo Townhouse for sale (Toronto C02) : MLS®# C12218903
133 Pears Avenue Annex Toronto M5R 1T3 $4,995,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12218903
- Bedrooms:
- 3
- Bathrooms:
- 4
Refined Urban Living At 133 Pears Avenue Where The Annex Meets Yorkville. The Largest Of Only Five Exclusive Town Homes. Enjoy All The Services And Amenities Of Its Upscale Adjoining Tower Residence Located Within The Prestigious Pears On The Avenue Community. Richly Appointed Designer Palette. This Residence Features A Magnificent Rooftop Terrace With A Fire Table, Bbq, Wood Floors, A Great Place to Entertain With An Abundance Of Blue Skies. Multiple Seating Areas And Balconies, Den Which Can Be Easily Transformed To A Third Bedroom, Multiple Walkouts, 10-Foot Ceilings, Ample Storage, Custom Built-Ins And Millwork, Designer And Builders Upgrades, Chef's Kitchen With Top Tier Miele Appliances. Private Elevator, Heated Floors, Smart Home Features - Work At Home Environment And Spacious Principal Rooms. A Luxurious Primary Suite With A Spa-Like Ensuite, Balcony And Large Walk-In Closet. Enjoy Two Underground Parking Spaces only a few steps from your door, Just Steps From Top-Tier Dining, Yorkville Shops and Walks and TTC. More detailsListed by RE/MAX REALTRON BARRY COHEN HOMES 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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