Direct: 416-371-9447 |

Kaija Pitt
Direct: 416-371-9447
Office: 416-960-9995
Sotheby’s Canada
1867 Yonge Street, Suite 100
Toronto ON M4S 1Y5 CA

South Hill

North of downtown Toronto, the neighbourhood of South Hillis dominated by a steep escarpment which allows residents here to enjoy stunning panoramic views of the city.Casa Loma, a castle-like mansion built in the early 1900s, is a Toronto landmark and popular tourist destination.


In the late 19th century, South Hill became home to some of Toronto’s wealthiest citizens. Atop the hill, a series of majestic manors were home to some of Toronto’s most influential residents. Senator John Macdonald built Oaklands, which today is part of the private De La Salle College. The Eaton family built Ardwold Estate and James Austin built Spadina House, which is now a museum. Many of the manors that were built on the hill have been demolished or converted to other uses. South Hill remains an upscale neighborhood in Toronto, and even features its own independent (and unofficial) republic, Rathnelly. This midtown community of about 250 homes, banded together in the 1960s to protest various proposed city developments including a roadway that would bisect their neighbourhood. Now the neighbourhood is home for many artists, musicians, writers, journalists and academics.


Defined by Avenue Road, South Hill contains some of the largest houses in Toronto. Mixed in with upscale homes are relatively new condominiums as well as some upscale rental apartment buildings. Families here appreciate the close proximity to some of the most highly regarded public, private and Catholic schools. South Hill is also close to George Brown College, and the Tarragon Theatre – Toronto’s leading venue for independent drama. South Hill is walking distance to the Royal Ontario Art Museum, University of Toronto, Yorkville, Bloor Street and the multi-cultural shops and festivals on St. Clair.


Joggers and those who love going for walks will appreciate the well-lit and family-friendly Nordheimer Ravine, which connects to Toronto’s Beltline Trail. Nearby is Winston Churchill Park, favoured for its running track, playground, and 10 tennis courts. The St. Clair Reservoir is popular with dog walkers.

South Hill Listings

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  • 412 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C14127468

    412 377 Madison Avenue Casa Loma Toronto M4V 3E1
    Main Photo: 412 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C14127468

    412 377 Madison Avenue Toronto M4V 3E1 Casa Loma

    $699,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C14127468
    Bedrooms:
    2
    Bathrooms:
    2
    Stylish South Hill Suite. Welcome to this thoughtfully designed 2-Bedroom, 2-Bathroom suite offering abundant in-suite storage and upgrades throughout. Designer kitchen features Carrara Marble countertops and backsplash, high-gloss cabinetry with soft-close drawers and a custom island with built-in dining table for four. Rich Sumo Antique Engineered Hardwood Flooring runs throughout the Living Room and Bedrooms. Primary Bedroom includes a wall-to-wall closet with built-ins and an upgraded 3-piece ensuite. The spacious and versatile 2nd bedroom offers flexibility to fit your lifestyle needs. The main 4-piece bathroom is conveniently located just across from the 2nd bedroom. Enjoy beautiful northern views of the treetops and the iconic Casa Loma turret from every window. The unit comes with a combined parking spot and private storage locker conveniently located just steps from the elevator lobby. The building offers 24 hour concierge service, gym, steam room, party room, media lounge and pet spa. Located in the desirable Brown Jr PS district. Mere steps to Dupont Station and an easy walk to local parks, green spaces and the vibrant shops and restaurants of the Annex and Yorkville. More details
    Listed by RE/MAX PRIME PROPERTIES - UNIQUE GROUP
    LISTING DETAILS

  • 336 380 Macpherson Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C14130328

    336 380 Macpherson Avenue Casa Loma Toronto M4V 3E3
    Main Photo: 336 380 Macpherson Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C14130328

    336 380 Macpherson Avenue Toronto M4V 3E3 Casa Loma

    $725,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C14130328
    Bedrooms:
    2
    Bathrooms:
    1
    Your plants want you to book a showing. Your friends will want to stay for dinner. Twelve-foot ceilings, exposed ductwork and a wall of windows make a strong first impression. But it's the morning coffee in your pyjamas, watching the sunrise without another building's living rooms looking back, that might get you attached. The original solarium doors are gone, opening that bright front space to everyday life. There's room to stretch out on the sofa, a place for the dining table and a modern kitchen that keeps whoever's cooking in the conversation. Dinner can run late. The dishes can wait. And your laptop? Leave it in the den. Tucked at the back, approximately 8 by 14 feet, it has room for a proper workspace, creative projects or overnight guests, with separation from where you spend your evening. Nobody's eating beside your inbox. The generous bedroom carries through the high ceilings and airy feel, ready when you're ready to call it a night. Outside, find your usual at Haute Coffee, meet friends at Fat Pasha or Playa Cabana, and pick up groceries on foot. Dupont subway is a short walk away. Come home to a quieter neighbourhood, friendly neighbours and approximately 889 sq. ft. at Madison Avenue Lofts. A gym downstairs, a rooftop terrace upstairs, concierge service and underground visitor parking make staying in and having people over equally appealing. Fibre optic internet, digital cable and a landline are included in the maintenance fees. Fair warning: you might become the friend who always hosts. More details
    Listed by KELLER WILLIAMS REFERRED URBAN REALTY
    LISTING DETAILS

  • Main 8 Glen Edyth Drive in Toronto: Casa Loma House for lease (Toronto C02) : MLS®# C14121890

    Main 8 Glen Edyth Drive Casa Loma Toronto M4V 2V7
    Main Photo: Main 8 Glen Edyth Drive in Toronto: Casa Loma House for lease (Toronto C02) : MLS®# C14121890

    Main 8 Glen Edyth Drive Toronto M4V 2V7 Casa Loma

    $4,400
    Residential Freehold
    Status:
    For Lease
    MLS® Num:
    C14121890
    Bedrooms:
    3
    Bathrooms:
    2
    Welcome to 8 Glen Edyth drive, your serene oasis in one of the city's most exclusive pockets. Fabulous 1,782 square foot, 3 bedroom, 2 bath apartment with rare garage parking. Generous house-sized spaces. Open concept living/dining accommodates full size furniture, perfect for entertaining. Enjoy evenings by the fire and views of a picturesque tree-lined street. Primary retreat with walk-in closet. All floors sound proofed. Elegant and timeless interiors .Fantastic location steps to Glen Edyth Drive Parkette, Davenport retail and restaurants. Coveted Brown School District. Walk to Dupont subway, shops, and grocery. George Brown College and U of T. AAA tenants only. More details
    Listed by SUTTON GROUP-ASSOCIATES REALTY INC.
    LISTING DETAILS

  • 11 Poplar Plains Crescent in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C14122088

    11 Poplar Plains Crescent Casa Loma Toronto M4V 1E9
    Main Photo: 11 Poplar Plains Crescent in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C14122088

    11 Poplar Plains Crescent Toronto M4V 1E9 Casa Loma

    $2,800,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C14122088
    Bedrooms:
    7
    Bathrooms:
    3
    Rare Opportunity For Well-Maintained Triplex In Sought After South Hill ! This Property Offers 2 Bright, 2 Bedroom Apartments With Separate Entrances. Additional unit On The Lower Level. All Three Units With Separate Entrance. 2 Garage Parkings And 1 Carpot, Total Of 3 Parkings. Fully Tenanted. Easy Walk To Yorkville, Summerhill, Cafes, Boutiques, Ttc..... More details
    Listed by TRADEWORLD REALTY INC
    LISTING DETAILS

  • 502 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C14120428

    502 377 Madison Avenue Casa Loma Toronto M4V 3E1
    Main Photo: 502 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C14120428

    502 377 Madison Avenue Toronto M4V 3E1 Casa Loma

    $598,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C14120428
    Bedrooms:
    2
    Bathrooms:
    1
    Welcome to South Hill on Madison. Sought-after boutique building, perfectly located in desirable Casa Loma. Thoughtfully designed one plus den unit with bright south exposure. Entertainer's kitchen features luxury built-in, paneled appliances and stone countertops. Host in style with a spacious den/dining area that easily accommodates a full dining setup. High-end, modern finishes and fixtures throughout and ensuite laundry nook. Generous living room with walkout to balcony. Quiet courtyard exposure. Unit comes with a fully enclosed locker room and covered parking spot. Enjoy the convenience of condo living: 24 hour concierge, gym, yoga room and more. Coveted Casa Loma location. Steps to subway, popular Dupont Strip cafes, shops and restaurants. The best of city living! More details
    Listed by SUTTON GROUP-ASSOCIATES REALTY INC.
    LISTING DETAILS

  • 207 394 Avenue Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C14115274

    207 394 Avenue Road Casa Loma Toronto M4V 2H4
    Main Photo: 207 394 Avenue Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C14115274

    207 394 Avenue Road Toronto M4V 2H4 Casa Loma

    $1,950
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C14115274
    Bedrooms:
    1
    Bathrooms:
    1
    *** 1 FREE month on a 1 year lease or 3 FREE months on an 18 month lease *** Professionals, Students and Newcomers welcome *** Rent controlled building *** Utilities included (heat, hydro, water) *** Located in the prestigious Forest Hill in the heart of the city, this charming building combines character suites and rental value. Minutes to shopping, restaurants, transportation and proximity to areas like: The Annex, Yorkville and the downtown financial district. Newly renovated apartments with all updated appliances and hardwood flooring. Laundry facilities in building. Trendy bistro and convenient store in the adjacent building. Utilities included (heat, water, hydro); portable ACs allowed More details
    Listed by RE/MAX REALTRON REALTY INC.
    LISTING DETAILS

  • 304 394 Avenue Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C14115300

    304 394 Avenue Road Casa Loma Toronto M4V 2H4
    Main Photo: 304 394 Avenue Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C14115300

    304 394 Avenue Road Toronto M4V 2H4 Casa Loma

    $1,795
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C14115300
    Bathrooms:
    1
    *** 1 FREE month on a 1 year lease or 3 FREE months on an 18 month lease *** Professionals, Students and Newcomers welcome *** Rent controlled building *** Utilities included (heat, hydro, water) *** Located in the prestigious Forest Hill in the heart of the city, this charming building combines character suites and rental value. Minutes to shopping, restaurants, transportation and proximity to areas like: The Annex, Yorkville and the downtown financial district. Newly renovated apartments with all updated appliances and hardwood flooring. Laundry facilities in building. Trendy bistro and convenient store in the adjacent building. Utilities included (heat, water, hydro); portable ACs allowed More details
    Listed by RE/MAX REALTRON REALTY INC.
    LISTING DETAILS

  • 204 2 Clarendon Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C14115298

    204 2 Clarendon Avenue Casa Loma Toronto M4V 1H9
    Main Photo: 204 2 Clarendon Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C14115298

    204 2 Clarendon Avenue Toronto M4V 1H9 Casa Loma

    $2,295
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C14115298
    Bathrooms:
    1
    *** 1 FREE months on a 1 year lease or 3 FREE months on an 18 month lease *** Rent controlled building *** Welcome to 2 Clarendon Ave, nestled in the heart of prestigious Forest Hill, where luxury living is redefined in a heritage building from the 1920s, meticulously restored with an unwavering attention to detail. The interior and exterior renovation marries timeless architecture with contemporary finishes, featuring oak hardwood floors, elegant granite countertops, high end appliances, and practical custom built-ins for maximum convenience. For elevated comfort, bathrooms are equipped with heated floors, heated towel racks, and fog-free mirrors. The grand patrimonial lobby, adorned with restored fragments of Casa Loma, leads to an array of newly updated common areas including a state-of-the-art gym equipped with a steam bath, a generously sized lounge, and a welcoming exterior terrace perfect sanctuaries for relaxation and socializing. The property is enveloped in lush landscaped surroundings that enhance its tranquil ambiance. Additional amenities tailored for modern living include a secure bike storage. Every urban amenity is just a short walk away, including transit, groceries, restaurants, shopping, parks and trails. Experience unparalleled sophisticated living where luxury and history blend seamlessly in one of Toronto's most esteemed locales. More details
    Listed by RE/MAX REALTRON REALTY INC.
    LISTING DETAILS

  • 210 380 Macpherson Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C14114592

    210 380 Macpherson Avenue Casa Loma Toronto M4V 3E3
    Main Photo: 210 380 Macpherson Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C14114592

    210 380 Macpherson Avenue Toronto M4V 3E3 Casa Loma

    $759,900
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C14114592
    Bedrooms:
    2
    Bathrooms:
    2
    Welcome To Unit 210 -380 Macpherson Avenue Lofts! Bright, Airy And Great Use Of Space. This 2 Bedroom Has 2 Bathrooms, 14ft Ceilings And Hard Loft Elements Throughout. Includes 1 Parking Spot And Newly Installed Owned . Indoor And Outdoor Bike Storage. Building Amenities Include: Gym, Party Room, Expansive Rooftop Deck w/ BBQ's, 24 Hour Concierge, Ample Visitor Parking, Meeting Room. Views Of Casa Loma And Courtyard From Balcony. Easy to Show! Living Dining Room AND Kitchen are Hardwood Floor Carpet in 2 Bedrooms, Urban Home At Newly-Completed Madison Avenue Lofts. Generous Floorplan Includes Master With Ensuite, Plus Second Bedroom / Den. Dramatic Ceilings To 14 Feet, Superb Kitchen, Dark Flooring And 75Sf Balcony. Quiet Location In Preferred Inner Courtyard. Convenient Location At The Foot Of Casa Loma, Steps To Annex / Yorkville, George Brown, U Of T. Parking Included. Available Immediately. More details
    Listed by REMAX YOUR COMMUNITY REALTY
    LISTING DETAILS

  • 410 380 Macpherson Avenue N in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C14109490

    410 380 Macpherson Avenue N Casa Loma Toronto M4V 3E3
    Main Photo: 410 380 Macpherson Avenue N in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C14109490

    410 380 Macpherson Avenue N Toronto M4V 3E3 Casa Loma

    $799,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C14109490
    Bedrooms:
    2
    Bathrooms:
    2
    Welcome To Unit 410 At Madison Avenue Lofts! Bright, Airy And Great Use Of Space. This 2 Bedroom Has 2 Bathrooms, 14ft Ceilings And Hard Loft Elements Throughout. Includes 1 Parking Spot And Newly Installed Owned EV CHARGER. Fibe Internet And TV Package Included In Condo Fees. Indoor And Outdoor Bike Storage. Building Amenities Include: Gym, Party Room, Expansive Rooftop Deck w/ BBQ's, 24 Hour Concierge, Ample Visitor Parking, Meeting Room. Views Of Casa Loma And Courtyard From Balcony. Easy to Show! Upgraded Floors, Newer Carpet in Bedrooms, Recently Painted. More details
    Listed by GREENFIELD REAL ESTATE INC.
    LISTING DETAILS

  • 216 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C14110984

    216 377 Madison Avenue Casa Loma Toronto M4V 3E1
    Main Photo: 216 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C14110984

    216 377 Madison Avenue Toronto M4V 3E1 Casa Loma

    $2,095
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C14110984
    Bedrooms:
    1
    Bathrooms:
    1
    CASA LOMA LIVING. SMART DESIGN. BOUTIQUE STYLE. Welcome to South Hill on Madison, a contemporary Art Deco-inspired boutique residence tucked into one of Toronto's most distinctive neighbourhoods at the foot of Casa Loma, where South Hill, Forest Hill, Yorkville and The Annex come together. This stylish suite delivers one of the smartest layouts in its class, with a defined bedroom area that creates separation from the main living space while maximizing functionality. The sleek kitchen features Caesarstone counters and built-in appliances, while thoughtful upgrades and space-saving features include a built-in desk, drop-down dining table, custom roller blinds and ensuite laundry. Designed for modern living, the flexible layout offers the freedom to create a space that reflects your lifestyle, whether you're working from home, relaxing or entertaining. Step outside to your private north-facing balcony, or unwind in the beautifully finished bathroom with marble details and a glass-enclosed shower. **The lifestyle extends well beyond your front door.** Just steps from Suite 216, the media room offers a welcoming extension of your living space, ideal for relaxing, watching a movie or enjoying a change of scenery. The gym is equally convenient, with both amenities located on the same level and no elevator or stairs required to access either. The building also features a stylish party room with terrace, offering another inviting setting to gather and entertain, along with concierge service and visitor parking. Leave the car behind! Dupont Subway Station is nearby, along with George Brown Polytechnic's Casa Loma Campus, neighbourhood cafés, restaurants, parks and everyday conveniences. An exceptional opportunity to enjoy sophisticated, intelligently designed Toronto living in a distinctive boutique setting. More details
    Listed by EXP REALTY
    LISTING DETAILS

  • 702 160 Balmoral Avenue in Toronto: Yonge-St. Clair Condo for lease (Toronto C02) : MLS®# C14107358

    702 160 Balmoral Avenue Yonge-St. Clair Toronto M4V 1J7
    Main Photo: 702 160 Balmoral Avenue in Toronto: Yonge-St. Clair Condo for lease (Toronto C02) : MLS®# C14107358

    702 160 Balmoral Avenue Toronto M4V 1J7 Yonge-St. Clair

    $2,050
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C14107358
    Bedrooms:
    1
    Bathrooms:
    1
    Discover comfortable city living in this spacious one-bedroom suite, ideally situated in the heart of sought-after Forest Hill! Enjoy beautiful northeast-facing views that fill the space with natural light and provide a lovely backdrop to everyday living. Located in a professionally managed 12-storey apartment building, this generously sized suite offers a comfortable and functional layout, perfect for those seeking space, convenience, and an exceptional Toronto location.Residents enjoy beautifully landscaped grounds, secure building entry, elevators, on-site laundry facilities, indoor and outdoor parking (Available on a monthly rental fee), and the convenience of an on-site superintendent.Exceptional Location! Ideally situated near Avenue Road and St. Clair, with TTC transit right at your corner and convenient subway access. Explore neighbourhood cafés, restaurants, grocery stores, parks, and everyday amenities. Enjoy easy access to Yorkville, downtown Toronto, Yorkdale Shopping Centre, hospitals, libraries, and community facilities. A wonderful opportunity to enjoy spacious one-bedroom living with beautiful northeast views in one of Toronto's most established and desirable neighbourhoods! More details
    Listed by EXP REALTY
    LISTING DETAILS
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Data was last updated November 1, 2026 at 06:15 AM (UTC)
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.
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This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.