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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46 Lowther Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12542994
46 Lowther Avenue Toronto M5R 1C6 
$7,995,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12542994
- Bedrooms:
- 6
- Bathrooms:
- 6
Behind the classic façade of 46 Lowther Avenue lies over 6,000 sqft. of beautifully curated living space designed for modern family life in the heart of Yorkville. Every detail has been thoughtfully planned from the open-concept kitchen that anchors the home, to the spacious family room that opens onto a private, estate-like landscaped oasis. The elegant living and dining room offer sophisticated spaces for entertaining, while the home's generous proportions and timeless finishes create an atmosphere of understated luxury. The primary bedroom is a peaceful retreat with a 6-piece spa-inspired ensuite with fireplace and walk-in closet. Two additional bedrooms and a convenient laundry room complete the second floor. The third-floor loft adds flexibility with two more bedrooms, a full bathroom, and ample storage perfect for growing families or guests. The lower level is designed for both comfort and lifestyle, featuring a nanny/bedroom suite with ensuite, wine cellar, lounge, gym, sauna, and abundant storage. Outdoors, the professionally landscaped backyard invites relaxation with multiple decks and lush greenery - a true escape in the city. Situated perfectly on one of Toronto's most desired and admired tree-lined streets, steps from Yorkville's world class shopping, Michelin Starred dining, and top schools, this residence combines elegance, functionality, and the most coveted downtown address. 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
-
3 85 Bedford Road in Toronto: Annex Condo Apartment for sale (Toronto C02) : MLS®# C12654118
3 85 Bedford Road Toronto M5R 2K3
$6,980,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12654118
- 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 free standing 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. PUBLIC OPEN HOUSE SUNDAY FEB 22, 2026 2-4PM 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
-
Garden Home 1 10 Prince Arthur Avenue in Toronto: Annex Condo Apartment for sale (Toronto C02) : MLS®# C12708350
Garden Home 1 10 Prince Arthur Avenue Toronto M5R 1A9
$6,695,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12708350
- Bedrooms:
- 4
- Bathrooms:
- 4
Welcome to Garden Home 1 at 10 Prince Arthur. A rare single-level residence in a boutique building of just 25 suites, offering three spacious bedrooms plus a family room, soaring 11-foot ceilings, and a quiet, fully landscaped private garden. Exceptional living spaces both inside and out, a chef's kitchen with Wolf and Sub-Zero appliances, gas fireplace, and an elegant primary suite with walk-in closets and a luxurious ensuite. Two additional ensuite bedrooms (one currently used as an office) each with ensuite and a large family room / den provide excellent flexibility. Designed by Richard Wengle with interiors by Brian Gluckstein and Michael London, this brand new building by celebrated North Drive presents an exceptional opportunity to live in a quiet pocket downtown. Residents enjoy 24-hour concierge, valet parking, private fitness facility, resident dining lounge, and courtyard sculpture garden. Ideally located in the Annex, steps to Avenue Road, Bloor Street, Yorkville, U of T, and nearby parks. Be first to call this unique residence "home". 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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302 10 Prince Arthur Avenue in Toronto: Annex Condo Apartment for sale (Toronto C02) : MLS®# C12612620
302 10 Prince Arthur Avenue Toronto M5R 1A9
$5,595,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12612620
- Bedrooms:
- 3
- Bathrooms:
- 3
A stylish corner suite at the newly completed 10 Prince Arthur. This brand-new residence offers an ideal split two-bedroom plan with separate den, 2.5 baths, and an exceptional west-facing private terrace of more than 550 square feet - perfect for everyday use and terrific outdoor entertaining. The suite features 10-foot ceilings, an expansive Cameo kitchen with Wolf and Sub-Zero appliances, and a bright exposure that delivers exceptional natural light. Developed by North Drive and designed by Richard Wengle, with interiors by Brian Gluckstein and Michael London, the building includes a limited number of residences and full services: 24-hour concierge, valet parking, a private fitness facility, resident lounge with catering kitchen, and a courtyard sculpture garden by Janet Rosenberg. Perfectly located in the Annex, steps to shopping, Yorkville dining, the University of Toronto, cultural venues and nearby parks. EXTRAS A unique urban home. Two-car underground parking, storage, and HST included. 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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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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46 Admiral Road in Toronto: Annex House for sale (Toronto C02) : MLS®# C12739880
46 Admiral Road Toronto M5R 2L5
$5,195,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12739880
- Bedrooms:
- 6
- Bathrooms:
- 5
The highly coveted Admiral Road. A grand, newly renovated 4+2 bedroom home awaits. Be awed by the massive scale and volume of space with over 4000sf above grade. A brilliant renovation that brings modern ease and enjoyment, but highlighting the charm and character of this magnificent residence. Formal living and dining rooms are accompanied by the open concept kitchen family room that opens to the private back garden. Second floor primary retreat with dressing room and spa-like 5-piece ensuite. Second floor den or office space with gas fireplace. Three additional bedrooms make for the perfect family home. Fully finished basement with guest room and semi ensuite, lower level family room and gym. 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
-
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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700 38 Avenue Road in Toronto: Annex Condo Apartment for sale (Toronto C02) : MLS®# C12500568
700 38 Avenue Road Toronto M5R 2G2
$4,980,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12500568
- Bedrooms:
- 3
- Bathrooms:
- 4
Privacy, luxury, location and space (approx. 3115 sq ft). Bring your vision to this beautiful condo nestled between Yorkville and The Annex. Join the residents of the The Prince Arthur in the south tower suite facing south, west and north. There are 3 bedrooms, 4 washrooms, a separate library, 2 balconies, 3 parking spaces, 2 lockers and visitor parking. Generous ensuite laundry area with laundry sink. Floor plans available. The circular drive entrance through the arches off of Avenue Road north of Bloor brings you to a private area where you experience discretion in a secure environment. The attentive Concierge and valets are experienced professionals providing valet parking, delivering packages to your suite and anticipating your needs. Wonderful amenities include the Annex and Yorkville Lounges, Fitness and Rejuvenation Center with sauna, theatre, library and car wash. Live in the innovative and 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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102 277 Davenport Road in Toronto: Annex Commercial for sale (Toronto C02) : MLS®# C12679136
102 277 Davenport Road Toronto M5R 1J9
$3,998,000 /For SaleCommercial- Status:
- Active
- MLS® Num:
- C12679136
- Total Area:
- 3,940 sq. ft.
Position your business where it commands attention. Situated in one of Toronto's most coveted and recognizable corridors, this high-exposure property offers exceptional walkability, seamless transit access, and immediate proximity to the city's most affluent lifestyle and cultural destinations. Whether establishing a flagship presence, a prestige office, or an elevated product showcase, this is a location that amplifies your brand the moment clients arrive.This is the kind of address that doesn't just give a business visibility - it defines how it is seen, experienced, and remembered. High exposure- Davenport Road offers exceptional walkability, strong transit access - just a five minute walk to both DuPont and Bay Subway stations and immediate proximity to Yorkville's luxury retail, dining, and cultural destinations. Zoned CR 2.0, this architecturally distinguished two-storey commercial space offers a rare balance of design presence and functional flexibility and benefits from constant visibility, strong street presence, and consistent pedestrian traffic. This is more than a commercial space - it is a statement address for brands and professionals who understand that where you are located matters. More detailsListed by INTERCITY 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
-
135 Madison Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12447205
135 Madison Avenue Toronto M5R 2S3
$3,995,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12447205
- Bedrooms:
- 6
- Bathrooms:
- 5
This grand dame home sits on the iconic Madison Avenue in the prime Annex. Circa 1905, 135 Madison Avenue is just under 4,000 square feet above grade and filled with original character including 4 fireplaces, original trim, wainscotting, crown moulding, and stained glass windows. The well proportioned house features 9.5' ceilings on the main floor, a large formal living room, dining room, an oversized kitchen with a butlers pantry, and a beautiful main floor family room that leads out to the lush garden. On the second floor you will find a generous primary bedroom with a sitting area, fireplace and a three piece ensuite. There are an additional 2 large bedrooms on the second floor as well as 2 full washrooms, a dedicated laundry room, and a large sunny deck. The third floor would make a fabulous primary suite and currently includes a large living room, kitchen, two additional bedrooms and a large deck with skyline and treetop views. The basement is partially finished with 7 foot ceilings and features a separate entrance. This home has been used as single family for many years but has potential for many layouts and possibilities including converting the property back into multiple units. Two car private drive parking and garden suite potential. The Annex speaks for its self with easy TTC, fabulous shops, restaurants, parks and schools. Floor plans attached to listing. Great opportunity for those looking for a co-ownership property! More detailsListed by BOSLEY 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®# C12720314
133 Pears Avenue Toronto M5R 1T3
$3,988,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12720314
- Bedrooms:
- 3
- Bathrooms:
- 4
Contemporary City Living Awaits At 133 Pears Avenue, Ideally Positioned Between The Charm Of The Annex And The Sophistication Of Yorkville. Tucked Away On A Peaceful Residential Street, This Residence Offers A Serene Escape While Remaining Moments From The Energy Of Downtown. The Largest Of Just Five Boutique Town Residences, It Provides Full Access To The Premium Services And Amenities Of The Connected Luxury Tower Within The Esteemed Pears On The Avenue Enclave. 2,782 Square Feet Of Luxurious Living Space. Showcasing A Thoughtfully Curated Interior Aesthetic, The Home Features An Expansive Rooftop Terrace Of Approximately 400 Square Feet, Complete With A Gas Fireplace, Built-In BBQ, And Refined Wood Decking. Hundreds Of Thousands In Design After Market Finishes. The Layout Includes Multiple Balconies And Outdoor Access Points, A Versatile Den Easily Converted Into A Third Bedroom, Soaring 10-Foot Ceilings, Generous Storage, Bespoke Cabinetry And Millwork, And Extensive Builder And Designer Enhancements Throughout. The Gourmet Kitchen Is Equipped With High-End Miele Appliances, Ideal For Both Everyday Living And Elevated Entertaining. Additional Highlights Include A Private In-Home Elevator, Heated Flooring, Integrated Smart Home Technology, Spacious Principal Rooms, And A Dedicated Work-From-Home Environment. The Primary Retreat Offers A Spa-Inspired Ensuite, Private Balcony, And A Substantial Walk-In Closet For Added Luxury And Comfort. Two Underground Parking Spaces Are Conveniently Located Just Steps From The Private Entrance, Complemented By 24-Hour Concierge Service. Perfectly Situated Near Ramsden Park, Acclaimed Restaurants, Yorkville's World-Class Shopping, Scenic Walking Routes, And TTC Access, This Exceptional Home Delivers Refined Urban Living At Its Finest. 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
-
46 Bernard Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12733138
46 Bernard Avenue Toronto M5R 1R2
$3,689,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12733138
- Bedrooms:
- 4
- Bathrooms:
- 4
Location, location! Welcome to 46 Bernard Avenue, an elegant 3+1 bedroom home in Toronto's prestigious Annex neighbourhood. Nestled on one of The Annex's most coveted streets, this Victorian home is a rare gem. This timeless residence blends historic character with modern comfort, featuring soaring ceilings, detailed mouldings, bright living spaces . The main floor offers a spacious living and dining area, perfect for entertaining with a wood-burning fireplace, alongside a spacious chef's kitchen with Caesarstone Quartz Counters and backsplash (2020). Upstairs, you'll find three bright and spacious bedrooms with ample storage, including a luxurious primary retreat with a wood-burning fireplace and a lavish 5-piece ensuite with heated marble tile floors and a double vanity, fully renovated in 2023. The versatile lower level includes an additional bedroom or office-ideal for guests or remote work. Enjoy your own private back patio oasis, perfect for morning coffee or summer evenings under the stars. Located within easy reach of transit, top schools, and cultural landmarks, this home delivers both prestige and convenience. 46 Bernard Avenue is more than just a home; it's a lifestyle. Embrace the charm, character, and prominence of this magnificent Annex address. Don't miss your chance to own a truly exceptional property in one of Toronto's most desirable communities. More detailsListed by Cottage Vacations Real Estate Brokerage 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 March 3, 2026 at 05:15 PM (UTC)
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