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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  • 31 Russell Hill Road in Toronto: Casa Loma House (3-Storey) for sale (Toronto C02) : MLS®# C11928496

    31 Russell Hill Road Casa Loma Toronto M4V 2S9
    Main Photo: 31 Russell Hill Road in Toronto: Casa Loma House (3-Storey) for sale (Toronto C02)  : MLS®# C11928496
    $10,995,000
    Freehold
    Status:
    Active
    MLS® Num:
    C11928496
    Bedrooms:
    7
    Bathrooms:
    9
    Spectacular South Hill Residence Designed By Architect Richard Wengle. One Of A Kind Over Looking South Valley. Over 9,135 Sf Of Luxury Living Space. Rear Gardens Boasting Stone Terrace, Swimming Pool And Hot Tub. Stone Exterior. Gated Entry To Face Mirrored 3 Car Garage. Exotic Woods & Stone Accents. Open Gourmet Kitchen-Family Room, Wet Bar/Wine Cellar. Elev. Large Paneled Library. Primary Retreat With Bar, His+Her Closet, Fireplace & 10-Piece Ensuite. Lower Level: Rec Room, Sitting Room, Mudroom And Nanny Suite. More details
    Listed by RE/MAX REALTRON BARRY COHEN HOMES INC.
  • 405 380 Macpherson Avenue in Toronto: Casa Loma Condo for lease (Toronto C02) : MLS®# C11925427

    405 380 Macpherson Avenue Casa Loma Toronto M4V 3E3
    Main Photo: 405 380 Macpherson Avenue in Toronto: Casa Loma Condo for lease (Toronto C02)  : MLS®# C11925427
    $4,090
    Condo
    Status:
    For Lease
    MLS® Num:
    C11925427
    Bedrooms:
    2
    Bathrooms:
    3
    Located in the prestigious Casa Loma neighborhood, this ultra-modern loft offers two well-appointed bedrooms and three luxurious bathrooms, including two ensuites. With a prime location just steps from Yorkville, Forest Hill, George Brown College, chic cafes, and world-class dining, it provides both convenience and elegance. Only a 5-minute walk to Dupont Station, the property features an open-concept kitchen with modern design elements and granite countertops, perfect for contemporary living. More details
    Listed by REALTY ONE GROUP FLAGSHIP
  • 203 195 Poplar Plains Road in Toronto: Casa Loma Condo for sale (Toronto C02) : MLS®# C11926386

    203 195 Poplar Plains Road Casa Loma Toronto M4V 2N3
    Main Photo: 203 195 Poplar Plains Road in Toronto: Casa Loma Condo for sale (Toronto C02)  : MLS®# C11926386
    $1,499,000
    Condo
    Status:
    Active
    MLS® Num:
    C11926386
    Bedrooms:
    1
    Bathrooms:
    2
    South Hill's best kept secret! Step inside this classic Georgian mansion. This inspired conversion by Bob Mitchell in 1994 features just six bespoke suites. Suite 203 boasts original oak floors, two fireplaces, a completely renovated kitchen, and an upper level primary retreat - complete with walkout balcony, walk in closet and generous primary bath. This unique walk-up unit celebrates the scale and beauty of the original architecture - a perfect balance of aesthetic and practical considerations. Be a part of this renowned established neighborhood without the hassle of upkeep involved in a freehold residence, or compromising community for a high rise shoebox condominium. For the discerning buyer, this is the community within the community you've been waiting for. Centrally located without compromising privacy, you'll be just a short walk to the shops at St Clair to the North, and Yorkville to the South. S/S Oven, S/S Refrigerator, B/I Microwave, B/I Dishwasher, Stacked Washer & Dryer, All ELFS, All WCs More details
    Listed by RE/MAX PROFESSIONALS INC.
  • 201 380 Macpherson Avenue in Toronto: Casa Loma Condo for lease (Toronto C02) : MLS®# C11923833

    201 380 Macpherson Avenue Casa Loma Toronto M4V 3E3
    Main Photo: 201 380 Macpherson Avenue in Toronto: Casa Loma Condo for lease (Toronto C02)  : MLS®# C11923833
    $3,200
    Condo
    Status:
    For Lease
    MLS® Num:
    C11923833
    Bedrooms:
    2
    Bathrooms:
    1
    Volume and space like nowhere else! Soft loft living with 14 foot ceiling heights in an unobstructed south-facing suite at the Madison Avenue Lofts in South Hill. Urban chic industrial-style floor-to-ceiling windows in a beautifully open concept living/dining/kitchen layout with balcony access from the living room. Proper privacy in the bedroom with a swing door to a dedicated room (no noise transferring drop walls like in some lofts), along with mirrored double closet doors, an operable window, and an additional access point in and out to the balcony. A separate den with sliding wooden barn doors, enclosing a very functional space that easily acts as a home office, workout space, area for a chaise lounge / pull-out couch, or many other functions! The L-shaped kitchen with an eat-in island and storage area, plus a coffee/bar cart, lends itself to plenty of work surfaces and loads of tall kitchen cupboard storage room. The spacious four-piece bathroom features marble tiles, a floating vanity and rain shower bathroom head. The south-facing balcony spans the entire width of the suite for unobstructed views of the downtown core, including an iconic view of the CN Towner. All 875 interior square feet of this loft are ready to enjoy starting March 1st, 2025! More details
    Listed by REAL ESTATE HOMEWARD
  • 217 380 Macpherson Avenue in Toronto: Casa Loma Condo for lease (Toronto C02) : MLS®# C11922382

    217 380 Macpherson Avenue Casa Loma Toronto M4V 3E3
    Main Photo: 217 380 Macpherson Avenue in Toronto: Casa Loma Condo for lease (Toronto C02)  : MLS®# C11922382
    $3,450
    Condo
    Status:
    For Lease
    MLS® Num:
    C11922382
    Bedrooms:
    2
    Bathrooms:
    1
    Beautifully Maintained Suite in the Madison Avenue Lofts. Quiet West Facing Unit with View of Casa Loma and Courtyard.Close to Everything - Schools, Parks, Transit and Shopping. 14 Ft Ceilings. Den Can be Used as a Second Bedroom. Underground Parking Space Included. Extra Features Include: Track Lighting, Built In Shelving in Closets, Extra Storage in Laundry Room. Unit Can be Offered Unfurnished As Well. No Short Term Rentals - Min.of 1 Yr. Thank You More details
    Listed by BOYLE COMMERCIAL
  • 306 380 Macpherson Avenue in Toronto: Casa Loma Condo for sale (Toronto C02) : MLS®# C11923043

    306 380 Macpherson Avenue Casa Loma Toronto M4V 3E3
    Main Photo: 306 380 Macpherson Avenue in Toronto: Casa Loma Condo for sale (Toronto C02)  : MLS®# C11923043
    $1,748,000
    Condo
    Status:
    Active
    MLS® Num:
    C11923043
    Bedrooms:
    3
    Bathrooms:
    2
    Absolutely Stunning Madison Avenue Loft! A Seamless Blend Of Contemporary Modern Features & Traditional Loft Elements. Magnificent Corner Unit Featuring: 14 Ft Ceilings, Tons Of Natural Light, Fireplace, 2 Balconies, Huge Open Concept Living/Dining Room, Parking, Locker & More. Shows To Perfection. A Sensational Property In A Wonderful Building! More details
    Listed by RIGHT AT HOME REALTY
  • 34 Poplar Plains Road in Toronto: Casa Loma House (3-Storey) for sale (Toronto C02) : MLS®# C11919945

    34 Poplar Plains Road Casa Loma Toronto M4V 2M8
    Main Photo: 34 Poplar Plains Road in Toronto: Casa Loma House (3-Storey) for sale (Toronto C02)  : MLS®# C11919945
    $4,299,000
    Freehold
    Status:
    Active
    MLS® Num:
    C11919945
    Bedrooms:
    4
    Bathrooms:
    4
    Client RemarksExquisite And Grand Detached Residence Centrally Nestled In Most Desired South Hill Enclave. This Classic Home Seamlessly Blends Timeless Finishes With Modern Flair. Designed For Family Living And Grand Entertaining. Graciously Proportioned Principal Rooms. Absolutely No Detail Overlooked. Peter Higgins Arch, Carey Mudford Design And Built By Le Boeuf. Architecturally Significant With Towering Ceilings & Cascading Sun Light. Picturesque CN Tower Views. Finest In Luxe Appts And Rich In Design. Gourmet Eat-In Kitchen With Island & Walk-Out To Gardens. Primary Bedroom With Marble Spa-Like Ensuite And Dressing Room. Upper Level Family Room With Fireplace And Exquisite Downtown Views. Lower Level With Rec Room. Expansive 2-Car Garage With Ample Storage And Heated Drive. Retreat To The Most Ideal Low Maintenance And Lush Backyard Gardens. Your Own Oasis In The Heart Of The City. Steps To Renowned Private And Public Schools, Parks, Ravine (Runners Paradise), TTC, Shops, And Eateries In The Annex, Yorkville And Summerhill. An Incredible Location And Residence That Cannot Be Missed. More details
    Listed by RE/MAX REALTRON BARRY COHEN HOMES INC.
  • 16 Clarendon Avenue in Toronto: Casa Loma House (2 1/2 Storey) for sale (Toronto C02) : MLS®# C11920356

    16 Clarendon Avenue Casa Loma Toronto M4V 1H9
    Main Photo: 16 Clarendon Avenue in Toronto: Casa Loma House (2 1/2 Storey) for sale (Toronto C02)  : MLS®# C11920356
    $5,995,000
    Freehold
    Status:
    Active
    MLS® Num:
    C11920356
    Bedrooms:
    6
    Bathrooms:
    5
    Spectacular Eden Smith Designed Residence. Nestled In The Heart Of Coveted South Hill. Complete Tranquility In The Heart Of The City. Over 6500Sf Of Meticulous Crafted Design On Sprawling 65Ft Frontage! Timeless And Classic Exterior. Exceptional Design And Flow. Sun Drenched Home. Abundance Of Storage. Graciously Proportioned Formal Principal Rooms. Private Main Floor Lib W/Fireplace. Curved Archways And Intricately Detailed Moldings. Sprawling Eat-In Kitchen With W/Walk Out To Deck And Gardens And Spacious Family Room. Second and Third Levels Feature Most Desirable 5 Bedroom Layout W/Additional Upper Level Family Room. Primary Bedroom W/Lavish 6PC Ensuite, Fireplace And Expansive Walk-in Closet. The Lower Level Boasts A Gym, Recreation Rm, Nanny Quarters, Spa Area W/Sauna and ample storage. Retreat To The Private Secluded Backyard Oasis With Lush Greenery And Yoga Studio, Perfect For Exercise, Work From Home Or Art Studio Space. Steps To Renowned Public And Private Schools, Parks, Ravine (Runners Paradise), TTC, Shops, And Eateries In Forest Hill, The Annex, Yorkville And Summerhill. More details
    Listed by RE/MAX REALTRON BARRY COHEN HOMES INC.
  • Lower 296 Avenue Road in Toronto: Casa Loma House (3-Storey) for lease (Toronto C02) : MLS®# C11919059

    Lower 296 Avenue Road Casa Loma Toronto M4V 2H1
    Main Photo: Lower 296 Avenue Road in Toronto: Casa Loma House (3-Storey) for lease (Toronto C02)  : MLS®# C11919059
    $1,975
    Freehold
    Status:
    For Lease
    MLS® Num:
    C11919059
    Bedrooms:
    1
    Bathrooms:
    1
    This newly renovated lower-level suite is ideally located close to all amenities. Offering a perfect blend of comfort, style and convenience, this modern space is ideal for individuals or couples looking for a cozy, private retreat. Featuring an open concept living & kitchen area with ample storage, brand new appliances, window and closet in the bedroom, and a separate entrance for privacy. Large shared backyard, separate ensuite laundry and utilities are all included. Steps to transit, grocery, shops and restaurants. More details
    Listed by PSR
  • 112 1 Benvenuto Place in Toronto: Casa Loma Condo for lease (Toronto C02) : MLS®# C11916534

    112 1 Benvenuto Place Casa Loma Toronto M4V 2L1
    Main Photo: 112 1 Benvenuto Place in Toronto: Casa Loma Condo for lease (Toronto C02)  : MLS®# C11916534
    $2,000
    Condo
    Status:
    For Lease
    MLS® Num:
    C11916534
    Bathrooms:
    1
    Luxurious & An Ultra Modern Unit Impeccably Designed To Perfection. Built-in, Remote-Controlled Murphy Bed. Located In The Exclusive Benvenuto, On A Private 4 Acre Hilltop Overlooking The City. Lobby With 24 Hr Concierge Service, Valet Parking For Guests & Day Porter. Amenities: Rooftop Fitness Studio, Outdoor Lounge Area & Guest Suites. Furnished. More details
    Listed by RE/MAX WEST REALTY INC.
  • 19 Clarendon Avenue in Toronto: Casa Loma House (2-Storey) for lease (Toronto C02) : MLS®# C11918153

    19 Clarendon Avenue Casa Loma Toronto M4V 1H8
    Main Photo: 19 Clarendon Avenue in Toronto: Casa Loma House (2-Storey) for lease (Toronto C02)  : MLS®# C11918153
    $20,000
    Freehold
    Status:
    For Lease
    MLS® Num:
    C11918153
    Bedrooms:
    3
    Bathrooms:
    4
    **Experience Luxury Living in Torontos Premier Neighborhood!** Welcome to this stunning, fully furnished 3-bedroom, 3.5-bathroom home near Avenue Rd & St. Clair Ave W. Boasting over 2,800 sq. ft. of impeccably designed living space, this immaculate property is perfect for your next short-term stay. **Spacious & Modern:** Open-concept layout with stylish decor and high-end finishes throughout. **Gourmet Chef's Kitchen:** Stainless steel appliances and everything you need to create culinary masterpieces. **Relaxation Redefined:** Enjoy the indoor sauna, unwind in the 5-piece ensuite bathroom, or soak under the stars in the outdoor hot tub. **Outdoor Paradise:** Landscaped front and backyards featuring a cozy lounge area with a fire table. **Convenient & Smart:** Electric blinds for added comfort and ease. **Turnkey Comfort:** Comes fully furnished with all items shown just bring your suitcase! Nestled in one of Toronto's most sought-after communities, you're steps away from trendy shops, fine dining, and lush parks. Whether you're here for business or leisure, this home offers the perfect blend of luxury and convenience.Book your stay today and indulge in the ultimate Toronto living experience! More details
    Listed by PMT REALTY INC.
  • 0207 223 St. Clair Avenue W in Toronto: Casa Loma Condo for sale (Toronto C02) : MLS®# C11916706

    0207 223 St. Clair Avenue W Casa Loma Toronto M4V 0A5
    Main Photo: 0207 223 St. Clair Avenue W in Toronto: Casa Loma Condo for sale (Toronto C02)  : MLS®# C11916706
    $1,199,999
    Condo
    Status:
    Active
    MLS® Num:
    C11916706
    Bedrooms:
    3
    Bathrooms:
    2
    A Rare Opprtunity To Own A Unit In This Exclusive Boutique Condo, Located In One Of Toronto's Most Prestigious Multi-million Dollar Neighborhoods- ' Forest Hill And South Hill" ! Known For its Exeptional Management And Pristine Maintanance, This Unique Building Rarely Sees Units Come Up For Sale Since Built in 2018 - " Nobody Wants To Leave" , Since In This Area , Nearly Impossible To Find A Unit Like This At This Price Point! This Remarkable 2+1 Sunfield Suite, Feels Like Very Brand New, With A Clear North View To The Beautiful Dunvegan Road, High Ceiling, Floor-To-Ceiling Windows, Extra Ceiling Lights In All Rooms, Elfs., A Large And Bright Den, Spacious Bathrooms, Lots Of Closets, Custom Made Closets And Vanity Desk, 24 Hr Concierge, Party Room, Recreation And Billiard Room, GYM, Pet SPA, Guest Suite , Visitor Parking, Bike Storage. Relax Or Entertain Your Guests In The Stunning 360- Degree , A MUST SEE PANORAMIC ROOFTOP TERRACE With A Spectacular CN Tower View, Includes Access TO BBQ, Lounge Area And A Full Kitchen/Bar! Enjoy The Convenience Of Owning Two Side-By-Side Parking Spots + One Locker, Close To Elevators! Over $45K Spent On High Quality Upgrades! Steps To Street Car, Just A FEW MINUTES Walk To Yonge & St.Clair Subway Station, Forest Hill Village, Great Super Markets, LCBO, Chic Boutiques, Fantastic Restaurants , SPAs And Famous Spots At Rosedale And Yorkville, Casa Loma , Parks, High-Ranked Private and Public Schools. Approximate 20 Minutes Drive To Union Station and To Yonge And HW 401, 10 Minutes Drive to Yonge And Eglinton LRT, 15 Minutes To U OF T , 30 Minutes To Pearson Airport And Countless Reasons To Call This Posh ,Safe, Well-established High-end Community Home - With Professional Neighbors, Exceptional Quality Of Life ,Or As A Smart Future Investment ! More details
    Listed by RIGHT AT HOME REALTY
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Data was last updated January 17, 2025 at 03:55 PM (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 Toronto Regional Real Estate Board. The data is deemed reliable but is not guaranteed to be accurate.