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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  • 201 2 Clarendon Avenue in Toronto: Yonge-St. Clair Condo for lease (Toronto C02) : MLS®# C8431684

    201 2 Clarendon Avenue Yonge-St. Clair Toronto M4V 1H9
    Main Photo: 201 2 Clarendon Avenue in Toronto: Yonge-St. Clair Condo for lease (Toronto C02)  : MLS®# C8431684
    $9,995
    Condo
    Status:
    For Lease
    MLS® Num:
    C8431684
    Bedrooms:
    3
    Bathrooms:
    3
    The Grande Dame of Forest Hill has returned! The 3 year year renovation is complete. No expense has been spared. Come and see perfection as it was meant to be. Yes we are pet friendly. More details
    Listed by SAGE REAL ESTATE LIMITED
  • 238 Spadina Road in Toronto: Casa Loma House (3-Storey) for sale (Toronto C02) : MLS®# C8434128

    238 Spadina Road Casa Loma Toronto M5R 2V1
    Main Photo: 238 Spadina Road in Toronto: Casa Loma House (3-Storey) for sale (Toronto C02)  : MLS®# C8434128
    $2,195,000
    Freehold
    Status:
    Active
    MLS® Num:
    C8434128
    Bedrooms:
    4
    Bathrooms:
    5
    Welcome to this exceptional freehold townhouse in the prestigious Castle Hill, nestled in the historical Casa Loma neighborhood. This elegant home offers 3+1 bedrooms/4.5 baths, spanning four levels, seamlessly serviced by an elevator, offering the epitome of city living and entertaining. Step into the well-appointed principal rooms, perfect for social gatherings and daily comfort. The fully equipped eat-in kitchen is a culinary dream, leading to a spacious living area that opens onto a beautiful deck, perfect for alfresco dining, barbecuing and relaxation. Adjacent to the kitchen, you will find an open dining area, ideal for hosting intimate dinners or lavish celebrations.The second level is designed for comfort and style, featuring a cozy family room with a wood-burning fireplace, a bedroom with double closet and a 3-piece washroom.Ascend to the third level, where the magnificent primary bedroom awaits. This luxurious retreat includes a walk-in closet, double closet and a lavish 5-piece ensuite bathroom. An additional bedroom with a double closet and 3-piece ensuite completes this floor.A delightful surprise awaits as you discover stairs leading to a charming loft area, with a walk-out to a stunning roof-deck, providing breathtaking views and an additional space for relaxation or entertaining.The lower level offers versatility with a finished recreation room or additional bedroom, a 4-piece washroom, a laundry room, and direct access to the garage with convenient 2-car tandem parking. Make this your new home and enjoy the best of urban living in a truly unique and sophisticated setting. More details
    Listed by SOTHEBY`S INTERNATIONAL REALTY CANADA
  • 0209 223 St. Clair Avenue W in Toronto: Casa Loma Condo for sale (Toronto C02) : MLS®# C8425866

    0209 223 St. Clair Avenue W Casa Loma Toronto M4V 0A5
    Main Photo: 0209 223 St. Clair Avenue W in Toronto: Casa Loma Condo for sale (Toronto C02)  : MLS®# C8425866
    $689,000
    Condo
    Status:
    Active
    MLS® Num:
    C8425866
    Bedrooms:
    2
    Bathrooms:
    1
    Spectacular 1Bdm + Den including Custom made Murphy Bed, Desk and Closet organizers on every room, Custom Made Island with Storage and attached dining table with two chairs, Including 1 Parking and 1 Locker, high end neighborhood, Schools and Walking distance to the TTC, Supermarket, Lcbo, Parks and Banks. Built-In, Integrated Appliances. Unit freshly painted just for you to feel like home. More details
    Listed by IPRO REALTY LTD.
  • 517 377 Madison Avenue in Toronto: Casa Loma Condo for sale (Toronto C02) : MLS®# C8425686

    517 377 Madison Avenue Casa Loma Toronto M4V 3E1
    Main Photo: 517 377 Madison Avenue in Toronto: Casa Loma Condo for sale (Toronto C02)  : MLS®# C8425686
    $959,000
    Condo
    Status:
    Active
    MLS® Num:
    C8425686
    Bedrooms:
    2
    Bathrooms:
    2
    Welcome to South Hill on Madison. A contemporary art deco condo located at foot of Casa Loma where Forest Hill meets the Annex! Steps from Dupont subway station. An exquisite boutique building in a quiet residential setting. Excellent loft style spacious 1050 sf living space ( 975 sf indoor + 75sf outdoor ) with primium Casa Loma views from the balcony, 2 beds + 2 baths + balcony + parking + private storage room right beside own parking spot . ( very few of the units in the building came with own private storage room . The rest of the storage lockers are all many lockers in one room )Rare offered World Class Amenaties in a small boutique building : 24hrs concierge, gym, yoga studio, pet spa+ visitors parking. Entire unit brand new wood floors,fresh painted & touched. Beautiful unit! Show like a new property !! More details
    Listed by RE/MAX WEST VICKY HSU GROUP REALTY
  • 202 195 Poplar Plains Road in Toronto: Casa Loma Condo for lease (Toronto C02) : MLS®# C8425644

    202 195 Poplar Plains Road Casa Loma Toronto M4V 2N3
    Main Photo: 202 195 Poplar Plains Road in Toronto: Casa Loma Condo for lease (Toronto C02)  : MLS®# C8425644
    $5,200
    Condo
    Status:
    For Lease
    MLS® Num:
    C8425644
    Bedrooms:
    1
    Bathrooms:
    2
    Elegant 2 Storey Jewel In Converted Georgian Mansion. Quiet Building With Lush South East Views. Approx 1500 S.F Of Renovated Sunfilled Space. Oversized Bedroom With Beamed Vaulted Ceilings & Walkout To A Private Deck. Loads Of Storage, Closets & B/I Bookcases. Unique Floor Plan Includes A Den/Library, Huge Dressing Room With B/I Desk . Open Concept Main Level With Gleaming Hardwood, Fire Place & Powder Room. Renovated Kitchen With Stainless Appliances & Granite Counters. Minimum 1 Year Lease. Boutique Building Feels More Like A House. Suite Has 2 Walkouts To Private Deck, 2 parking spaces (one suited for small car only) & Large Locker. More details
    Listed by CHESTNUT PARK REAL ESTATE LIMITED
  • 0209 223 St. Clair Avenue W in Toronto: Casa Loma Condo for lease (Toronto C02) : MLS®# C8424380

    0209 223 St. Clair Avenue W Casa Loma Toronto M4V 0A5
    Main Photo: 0209 223 St. Clair Avenue W in Toronto: Casa Loma Condo for lease (Toronto C02)  : MLS®# C8424380
    $2,600
    Condo
    Status:
    For Lease
    MLS® Num:
    C8424380
    Bedrooms:
    2
    Bathrooms:
    1
    Take advantage of Rent offer in "Extras" Spectacular 1Bdm + Den including Custom made Murphy Bed, Desk and Closet organizers on every room, Custom Made Island with Storage and attached dining table with two chairs, Including 1 Locker, high end neighborhood, Schools and Walking distance to the TTC, Supermarket, Lcbo, Parks and Banks. Built-In, Integrated Appliances. Parking available at an additional Fee, unit freshly painted just for you to feel like home. More details
    Listed by IPRO REALTY LTD.
  • 516 223 St Clair Avenue W in Toronto: Casa Loma Condo for lease (Toronto C02) : MLS®# C8421538

    516 223 St Clair Avenue W Casa Loma Toronto M4V 1R3
    Main Photo: 516 223 St Clair Avenue W in Toronto: Casa Loma Condo for lease (Toronto C02)  : MLS®# C8421538
    $2,550
    Condo
    Status:
    For Lease
    MLS® Num:
    C8421538
    Bedrooms:
    1
    Bathrooms:
    1
    Light, Bright, & White! This Well Classy, Laid Out One Bedroom Condo With Your Very Own Parking Spot. Equipped With Laminate Flooring Throughout, A Clean & Modern Kitchen, Large Bedroom W/ Walk-In Closet, & A Balcony Long Enough For Your Daily Sprints! Spectacular Amenities & Rooftop Views. Parking & Locker included. More details
    Listed by SMART SOLD REALTY
  • 306 1 Benvenuto Place in Toronto: Casa Loma Condo for sale (Toronto C02) : MLS®# C8422296

    306 1 Benvenuto Place Casa Loma Toronto M4V 2L1
    Main Photo: 306 1 Benvenuto Place in Toronto: Casa Loma Condo for sale (Toronto C02)  : MLS®# C8422296
    $1,585,000
    Condo
    Status:
    Active
    MLS® Num:
    C8422296
    Bedrooms:
    2
    Bathrooms:
    2
    Welcome to the Benvenuto - Rarely offered 2 bed, 2 bath suite with over 1100 sq ft of modern living space. Generously sized Rooms, N facing with tons of Natural Light! Fabulous finishes to excite the most discerning buyers! Located on a private hilltop, amenities include 24 hr concierge, valet, rooftop gym, and guest suite. Includes 1 parking space & 1 locker. Own a piece of Toronto's most prestigious Real estate at this Heritage Landmark. More details
    Listed by HARVEY KALLES REAL ESTATE LTD.
  • 103 1 Clarendon Avenue in Toronto: Annex Condo for lease (Toronto C02) : MLS®# C8418198

    103 1 Clarendon Avenue Annex Toronto M4V 1H8
    Main Photo: 103 1 Clarendon Avenue in Toronto: Annex Condo for lease (Toronto C02)  : MLS®# C8418198
    $5,200
    Condo
    Status:
    For Lease
    MLS® Num:
    C8418198
    Bedrooms:
    2
    Bathrooms:
    1
    Grand 1800 Sq. Ft. Apartment With Incredible Architectural Detailing Of The Claridge Apartments Built In 1927.There's Loads Of Space Here To Live & Play! Picture This - Newly Renovated With Really High Ceilings, Lots Of Windows, Wood-Burning Fireplace, Parquet Flooring & Stainless Steel Appliances. Exceptionally Large Dining And Living Rooms For Your Entertainment Enjoyment. Grand 2 Bdrm With Long Gracious Foyer & Galley Hall. Vibrant & Trendy Neighbourhood! More details
    Listed by CHESTNUT PARK REAL ESTATE LIMITED
  • 14 423 Avenue Road in Toronto: Yonge-St. Clair Condo for sale (Toronto C02) : MLS®# C8405374

    14 423 Avenue Road Yonge-St. Clair Toronto M4V 2H7
    Main Photo: 14 423 Avenue Road in Toronto: Yonge-St. Clair Condo for sale (Toronto C02)  : MLS®# C8405374
    $1,859,000
    Condo
    Status:
    Active
    MLS® Num:
    C8405374
    Bedrooms:
    3
    Bathrooms:
    3
    Unknown to many, this boutique condominium at 423 Avenue Road is South Hill's best kept secret. Offering only one unit per floor, just fourteen residents occupy the building, making for an exclusive and discreet luxury residence in the heart of the city. This penthouse suite spans 1,816 square feet with truly the most remarkable views in every direction. A direct elevator opens to the foyer with a double closet and two piece bathroom, and then guests are quickly drawn into the gorgeous living room with the oversized windows overlooking the city. The living room is expansive, with dimensions of 20 feet by 18.3 feet. It is lined with pretty millwork and wainscotting details, and really is a superb room to enjoy and entertain in. The dining room is lined with designer grasscloth wallpaper, and quickly connects to the the renovated kitchen with granite countertops, high end stainless appliances, and the most picture-perfect breakfast bar that overlooks the campus of De La Salle, with sight lines straight down to the waterfront. The king-sized bedroom offers a wall of custom closets, a beautifully appointed ensuite bathroom, and has electronic black-out blinds on the windows. Adjacent to it, a raised sitting room makes for the most picturesque setting to enjoy the sightline view of the city, straight down Avenue Road. The second bedroom has an independent ensuite, a concealed closet, and access to the full-sized laundry. Work from home in the most incredible setting with inspiring west city and lake views. Exterior space is enjoyed on the enclosed balcony or the astounding rooftop deck just one flight of stairs up from this suite. Enjoy morning yoga or a glass of wine with a friend at the end of the day with truly the best perch in the city on this rooftop. More details
    Listed by CHESTNUT PARK REAL ESTATE LIMITED
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  • 187 Cottingham Street in Toronto: Casa Loma House (3-Storey) for sale (Toronto C02) : MLS®# C8406490

    187 Cottingham Street Casa Loma Toronto M4V 1C5
    Main Photo: 187 Cottingham Street in Toronto: Casa Loma House (3-Storey) for sale (Toronto C02)  : MLS®# C8406490
    $4,675,000
    Freehold
    Status:
    Active
    MLS® Num:
    C8406490
    Bedrooms:
    4
    Bathrooms:
    3
    Gracefully set back from the street on coveted, quiet Cottingham in The Republic of Rathnelly, stands this exquisite turn-key home. Built in 1890, as one of the few detached homes on the street, 187 Cottingham is truly a great dame of the neighbourhood. In 2013 the home underwent a full back-to-the-brick restoration, meticulously overseen by the current homeowners, realized by Shima Homes. Their goal was to restore the handsome exterior, honouring the Victorian architecture of the streetscape while reimagining the interior spaces with modern conveniences and the efficiency of daily life in mind. The renovation included up-to-date building systems, intuitive planning, thoughtful design and a quality of craftsmanship that one must experience. The result; an elegant, timeless, turn-key home for the discerning homeowner. The main floor features soaring ceiling heights reaching over 10 feet, enhancing the sense of space and light. Meticulously crafted plaster molding and wall paneling create a sophisticated timeless elegance. Custom milled kitchen features highly organized storage, top of the line appliances and a breakfast bar. The butler's pantry / bar walks conveniently through to the dining room. Step down into the light filled living room with 11'9" ceiling heights, gas fireplace and french doors that walk out to the lush, landscaped backyard. The main floor was designed for entertaining and easy every day living. Incredible skylight and southern exposure drenches the home in sunlight. The second storey houses the primary suite with a luxurious 5pc ensuite, large walk-in closet and built-ins. The second floor family room is a wonderful place to unwind at the end of the day features a wood burning fireplace. The third floor houses two additional spaces, a bedroom and a home office that walks-out to south facing terrace with picturesque city skyline views in the distance. The den and office were both designed to easily be converted into bedrooms should one desire. More details
    Listed by CHESTNUT PARK REAL ESTATE LIMITED
  • 19 Clarendon Avenue in Toronto: Casa Loma House (2-Storey) for sale (Toronto C02) : MLS®# C8400444

    19 Clarendon Avenue Casa Loma Toronto M4V 1H8
    Main Photo: 19 Clarendon Avenue in Toronto: Casa Loma House (2-Storey) for sale (Toronto C02)  : MLS®# C8400444
    $3,739,000
    Freehold
    Status:
    Active
    MLS® Num:
    C8400444
    Bedrooms:
    3
    Bathrooms:
    4
    Contemporary, inviting, and architecturally beautiful home with a low-maintenance Yard. Open concept layout with spacious rooms and enormous windows. This home is perfect for entertaining. Backyard Oasis and Spa-like atmosphere with Sauna, Hot tub, fire pit, and exquisite restrooms. Located in the highly desirable South Hill neighbourhood, close to Yorkville, Summerhill, Rosedale, and Forest Hill. In the Brown School District and surrounded by private schools, including Upper Canada College, Bishop Strachan School, and York School. There is parking for four vehicles. More details
    Listed by PMT REALTY INC.
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Data was last updated June 13, 2024 at 11:55 AM (UTC)