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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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  • 101 321 Davenport Road in Toronto: Annex Condo for sale (Toronto C02) : MLS®# C10234049

    101 321 Davenport Road Annex Toronto M5R 1K5
    Main Photo: 101 321 Davenport Road in Toronto: Annex Condo for sale (Toronto C02)  : MLS®# C10234049
    $6,799,990
    Condo
    Status:
    Active
    MLS® Num:
    C10234049
    Bedrooms:
    3
    Bathrooms:
    3
    Tucked away in the vibrant heart of the Annex, 321 Davenport is just a leisurely stroll from Yorkville's premier attractions, sophisticated boutiques, and rejuvenating wellness centers. This residence epitomizes luxury living in Toronto, where high-end design seamlessly converges with minimalist elegance, tailored for the city's most discerning residents. Comprising only 18 exceptional units, this opulent three-bedroom, three-bathroom home features approximately 2,708 SQFT Interior | 1,711 SQFT Exterior exquisitely designed space. The homes standout feature is an expansive 1,711-square-foot private terrace, complete with an option of having a serene pool that beckons for relaxation and leisure. Inside, the residence is enhanced by an array of top-tier upgrades, each meticulously selected to redefine modern sophistication and comfort. More details
    Listed by THE AGENCY
    Tanya Crepulja
    Steven Fontes
  • 43 Bernard Avenue in Toronto: Annex House (2 1/2 Storey) for sale (Toronto C02) : MLS®# C11047417

    43 Bernard Avenue Annex Toronto M5R 1R3
    Main Photo: 43 Bernard Avenue in Toronto: Annex House (2 1/2 Storey) for sale (Toronto C02)  : MLS®# C11047417
    $5,845,000
    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. More details
    Listed by PROPERTY.CA INC.
    Tanya Crepulja
    Steven Fontes
  • 37 Madison Avenue in Toronto: Annex House (3-Storey) for sale (Toronto C02) : MLS®# C9416378

    37 Madison Avenue Annex Toronto M5R 2S2
    Main Photo: 37 Madison Avenue in Toronto: Annex House (3-Storey) for sale (Toronto C02)  : MLS®# C9416378
    $5,500,000
    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 details
    Listed by RE/MAX REALTRON REALTY INC.
    Tanya Crepulja
    Steven Fontes
  • 37 Madison Avenue in Toronto: Annex Property for sale (Toronto C02) : MLS®# C9416439

    37 Madison Avenue Annex Toronto M5R 2S2
    Main Photo: 37 Madison Avenue in Toronto: Annex Property for sale (Toronto C02)  : MLS®# C9416439
    $5,500,000 /For Sale
    Commercial
    Status:
    Active
    MLS® Num:
    C9416439
    Total Area:
    7,262 sq. ft.
    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 details
    Listed by RE/MAX REALTRON REALTY INC.
    Tanya Crepulja
    Steven Fontes
  • 808 38 Avenue Road in Toronto: Annex Condo for sale (Toronto C02) : MLS®# C10429285

    808 38 Avenue Road Annex Toronto M5R 2G2
    Main Photo: 808 38 Avenue Road in Toronto: Annex Condo for sale (Toronto C02)  : MLS®# C10429285
    $5,490,000
    Condo
    Status:
    Active
    MLS® Num:
    C10429285
    Bedrooms:
    4
    Bathrooms:
    5
    The Prince Arthur! Direct elevator access into this magnificent & rarely offered suite! Feels like a bungalow in the sky! Featuring 3 bedrooms & 5 bathrooms, east views over Yorkville & west sunset views. Expansive dining room opens to living room w/fireplace & library. Large primary bedroom located in a private wing features His & Hers ensuites, His & Hers W/I closets, seating area & W/O to balcony. Beautiful spacious kitchen w/centre island & breakfast area. 2nd bedroom with 4 pc. ensuite & W/I closet. 3rd bedroom or office with W/O to balcony. Crown moulding & beautiful millwork throughout. Lots of storage space. The superb 24 hr. concierge team provides supreme service to meet your every whim. This is the luxury address you've been waiting for with approx. 3500 S.F. of quiet & distinctive living space in the heart of Yorkville. A vibrant loc'n adjacent to Yorkville Village, Whole Foods, fine dining, outdoor patios, world renowned shops, The Rom, art galleries & public transit. More details
    Listed by ROYAL LEPAGE/J & D DIVISION
    Tanya Crepulja
    Steven Fontes
  • 12 Madison Avenue in Toronto: Annex Property for sale (Toronto C02) : MLS®# C9351416

    12 Madison Avenue Annex Toronto M5R 2S1
    Main Photo: 12 Madison Avenue in Toronto: Annex Property for sale (Toronto C02)  : MLS®# C9351416
    $5,450,000 /For Sale
    Commercial
    Status:
    Active
    MLS® Num:
    C9351416
    Major Bus.:
    Professional Office
    Total Area:
    4,093 sq. ft.
    Strategically situated within The Annex, 'Ecology House' is an exceptional freestanding opportunity within one of the city's most affluent downtown neighbourhoods. This grand Annex Victorian offers the ideal blend of refined sophistication and modern functionality. Spanning three storeys and 4,093 sq ft (approx) above grade, this property has been designed to serve both elevated professional requirements and the aesthetic appreciation of historical architecture. Its current configuration as a private practice offers a reception area, boardroom, nine private offices, an open co-working area, a fully equipped chef's kitchen and washrooms on each floor. Thoughtful consideration has been made to the property's heritage with sophisticated renovations and comprehensive restoration to the architectural details that reflect its significance. From custom millwork, integrated file storage systems and crown mouldings to restored banisters and exterior brickwork. The property's mixed zoning combined with a site area of 4,144 sq ft allows for a wide range of commercial and/or residential uses, with potential for expansion, making it ideal for end-users or value add investors. Located steps to Bloor St West, Yorkville and Spadina TTC, the property's positioning offers convenience and discretion. More details
    Listed by SOTHEBY`S INTERNATIONAL REALTY CANADA
    Tanya Crepulja
    Steven Fontes
  • 12 Madison Avenue in Toronto: Annex House (3-Storey) for sale (Toronto C02) : MLS®# C9351411

    12 Madison Avenue Annex Toronto M5R 2S1
    Main Photo: 12 Madison Avenue in Toronto: Annex House (3-Storey) for sale (Toronto C02)  : MLS®# C9351411
    $5,450,000
    Freehold
    Status:
    Active
    MLS® Num:
    C9351411
    Bedrooms:
    11
    Bathrooms:
    3
    For those seeking to merge the elegance of the past with the luxury of the present, 'Ecology House' stands as an extraordinary property within one of the city's most desirable downtown neighbourhoods. This grand Annex Victorian offers the ideal blend of refined sophistication and contemporary functionality, designed with the decerning homeowner in mind. Set across three stories and offering approximately 4,093 sq ft of living space, this home embraces both the grandeur of its historical past and the comfort of modern living. Currently configured to accommodate a private practice, this property lends to an effortless transition into a luxurious family residence. The layout comprises a foyer, grand living room, seven bedrooms with potential for additional rooms, two open den/sitting areas, a gourmet kitchen and bathrooms across each floor for convenience. Every corner of the property reflects meticulous attention to preserving the architectural integrity, with sophisticated renovations enhancing its historical charm. From the bespoke custom millwork and integrated storage solutions to the restored banisters, and the building's striking red brickwork facade, the property pays homage to its heritage while catering to modern aesthetics and comfort.The property stands on a generous site of approximately 4,144 sq ft, its mixed zoning affords a realm of possibilities for customization or expansion to suit your lifestyle needs. Whether envisaging a grand family estate or a bespoke blend of work and play, this home adapts to your vision of sophisticated urban living.Positioned just steps from the vibrant Bloor St West, the boutiques of Yorkville, and the seamless connectivity to transit, 'Ecology House' combines the tranquility of residential life with the conveniences of city living. More details
    Listed by SOTHEBY`S INTERNATIONAL REALTY CANADA
    Tanya Crepulja
    Steven Fontes
  • 102 277 Davenport Road in Toronto: Annex Property for sale (Toronto C02) : MLS®# C9361172

    102 277 Davenport Road Annex Toronto M5R 1J9
    Main Photo: 102 277 Davenport Road in Toronto: Annex Property for sale (Toronto C02)  : MLS®# C9361172
    $5,249,000 /For Sale
    Commercial
    Status:
    Active
    MLS® Num:
    C9361172
    Total Area:
    3,663 sq. ft.
    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. More details
    Listed by SOTHEBY`S INTERNATIONAL REALTY CANADA
    Tanya Crepulja
    Steven Fontes
  • 2 350 Davenport Road in Toronto: Annex Condo for sale (Toronto C02) : MLS®# C9392479

    2 350 Davenport Road Annex Toronto M5R 1K6
    Main Photo: 2 350 Davenport Road in Toronto: Annex Condo for sale (Toronto C02)  : MLS®# C9392479
    $4,900,000
    Condo
    Status:
    Active
    MLS® Num:
    C9392479
    Bedrooms:
    3
    Bathrooms:
    3
    Final remaining suite! An architectural gem that fosters an atmosphere of intimacy and privacy, this masterpiece residence promises to redefine your notion of upscale living. With unparalleled attention to detail, this 8-storey luxury condominium unveils a mere six residences, ensuring a world of discretion & exclusivity. 2-storey home with ceilings up to 20 feet high. Private stone terrace with 15 feet trees of your choice. Solid core wood doors and custom finishes to the highest standard. More details
    Listed by SOTHEBY`S INTERNATIONAL REALTY CANADA
    Tanya Crepulja
    Steven Fontes
  • 111 38 Avenue Road in Toronto: Annex Condo for sale (Toronto C02) : MLS®# C9769123

    111 38 Avenue Road Annex Toronto M5R 2G2
    Main Photo: 111 38 Avenue Road in Toronto: Annex Condo for sale (Toronto C02)  : MLS®# C9769123
    $4,595,000
    Condo
    Status:
    Active
    MLS® Num:
    C9769123
    Bedrooms:
    3
    Bathrooms:
    3
    Luxury and style await at The Prince Arthur, one of Toronto's most exclusive addresses. Newly renovated with no stone left unturned, this spectacular 2-storey townhome offers a rare opportunity in the heart of Yorkville. Expansive open concept main floor is an entertainer's dream with 10 ft ceilings, white oak herringbone floors and designer light fixtures. Striking glass staircase with custom wine storage overlooks spacious dining room. Living room with coffered ceiling, floor-to-ceiling Nero Marquina fireplace and oversized windows. Chef's kitchen featuring 14 ft center island, Subzero refrigerator, Miele appliances, Pro Chef stainless steel sink and custom backsplash. Walk-out to a terrace one can only dream of with 400 sq ft of tranquility in your own private garden overlooking a manicured courtyard. Second floor featuring generously sized primary bedroom with coffered ceiling and walk-in closet with custom built-ins. Ultra-luxurious primary bath with 70" Baden Italy double vanity and Knief freestanding tub. Second bedroom with mirrored recessed ceiling. Steps to cafes, boutiques, restaurants, museums and everything Yorkville has to offer. More details
    Listed by HARVEY KALLES REAL ESTATE LTD.
    Tanya Crepulja
    Steven Fontes
  • 65 Elgin Avenue in Toronto: Annex House (3-Storey) for sale (Toronto C02) : MLS®# C9364637

    65 Elgin Avenue Annex Toronto M5R 1G5
    Main Photo: 65 Elgin Avenue in Toronto: Annex House (3-Storey) for sale (Toronto C02)  : MLS®# C9364637
    $4,500,000
    Freehold
    Status:
    Active
    MLS® Num:
    C9364637
    Bedrooms:
    4
    Bathrooms:
    4
    This East Annex Victorian home was built in 1891 by Toronto architect W.A. Langton steps away from Yorkville and other downtown luxury amenities. This five-level semi-detached home boasts a huge basement with 3.14M ceilings fit for a squash court, pool, bowling alley, games room or whateveryou fancy. Furnished with oak and marble floors; three-level walnut staircase; six travertine marble fireplaces. Spacious living and dining room with 3.17M ceilings. The renovated kitchen has updated appliances. Corner house with bright morning and afternoon light that streams through oversizedbay windows. A private backyard garden oasis perfect for events or just relaxing is surrounded by lush vegetation. The detached garage has parkingspaces for large vehicles. Impeccably maintained, truly a rare find only blocks away from U of T - Varsity Stadium, excellent schools, public transit,shops, restaurants, museums, galleries and more. This unique opportunity awaits the most discerning buyer. More details
    Listed by HARVEY KALLES REAL ESTATE LTD.
    Tanya Crepulja
    Steven Fontes
  • 40 Admiral Road in Toronto: Annex House (3-Storey) for sale (Toronto C02) : MLS®# C9378019

    40 Admiral Road Annex Toronto M5R 2L5
    Main Photo: 40 Admiral Road in Toronto: Annex House (3-Storey) for sale (Toronto C02)  : MLS®# C9378019
    $4,498,000
    Freehold
    Status:
    Active
    MLS® Num:
    C9378019
    Bedrooms:
    8
    Bathrooms:
    5
    Located in Prime Annex/Yorkville and nestled on an iconic, most coveted street, this home has an address of distinction. Conveniently just steps away from galleries, shops, restaurants, and both lines of the TTC, this gracious home's character is immediately evident with its spacious principal rooms, leaded glass windows, high ceilings, and original woodwork converging to create an ambiance of classic elegance. There are multiple fireplaces throughout the home, high baseboards, cast iron radiators, and original wainscotting. The main floor boasts a large living room, an elegant dining room, a chef's kitchen, and a cozy breakfast room with French doors opening to a back deck and a private garden. Two staircases lead to the second floor which features a large primary bedroom retreat with walk-through closet, new 4 piece ensuite bath, and sunroom. French glass doors lead to a large second bedroom or sitting room/family room with another new 3 piece ensuite bath. There is laundry on the second floor. His and Hers separate Bathrooms second floor! More details
    Listed by CHESTNUT PARK REAL ESTATE LIMITED
    Tanya Crepulja
    Steven Fontes
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Data was last updated November 28, 2024 at 11:55 AM (UTC)
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