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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  • 128 380 Macpherson Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12345431

    128 380 Macpherson Avenue Casa Loma Toronto M4V 3E3
    Main Photo: 128 380 Macpherson Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12345431

    128 380 Macpherson Avenue Toronto M4V 3E3 Casa Loma

    $3,000
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C12345431
    Bedrooms:
    2
    Bathrooms:
    1
    Your dream loft life awaits, a stunning and stylish true hard loft with 16ft ceilings, parking, locker, a private patio entrance, and excellent building amenities - just steps from the subway. This bright and airy loft features floor to ceiling windows with sunny east exposure. A modern kitchen W/ stainless steel appliances & granite countertops, a spacious den - perfect for your new home office, and a large laundry room and entryway with ample storage that serves as a second WFH option. The best of both worlds, close proximity to both a beautiful ravine and all your essentials as well as UofT, George Brown, The Annex, Yorkville, shopping and restaurants of downtown while tucked away from the hustle and bustle. Bell Internet and Fibe included through building! More details
    Listed by BOSLEY REAL ESTATE LTD.
    LISTING DETAILS

  • 323 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12345008

    323 377 Madison Avenue Casa Loma Toronto M4V 3E1
    Main Photo: 323 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12345008

    323 377 Madison Avenue Toronto M4V 3E1 Casa Loma

    $1,950
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C12345008
    Bedrooms:
    1
    Bathrooms:
    1
    A Boutique Art Deco Designed Residence At The Foot Of Castle Loma. Bright And Charming With A Modern Kitchen. Floor To Ceiling Windows, Modern Kitchen With S/S Appliances. Very Conveniently Steps To Dupont Subway , Shops, Dining within South Hill, Forest Hill, Dupont, the Annex, And The Wonderful Castle Loma! Great Amenities Include Gym, Yoga Studio, Pet Spa, 24Hr Concierge. More details
    Listed by HOMELIFE/PROSPERITY LAND REALTY INC.
    LISTING DETAILS

  • 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C12345263

    314 377 Madison Avenue Casa Loma Toronto M4V 3E1
    Main Photo: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C12345263

    314 377 Madison Avenue Toronto M4V 3E1 Casa Loma

    $749,900
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C12345263
    Bedrooms:
    2
    Bathrooms:
    2
    Unique opportunity to own a stunning boutique condo in one of Torontos most desirable neighborhoods, right by Casa Loma. This exceptional 2-bedroom, 2-bathroom home offers an exquisite blend of luxury, charm, and convenience. From the modern, open-concept layout to the high-end finishes, every detail has been carefully crafted. Large windows bring in abundant natural light, while the spacious bedrooms and elegant bathrooms provide comfort and style. Located near Torontos historic Casa Loma, this condo is close to vibrant dining, shopping, and cultural destinations, with easy access to transit options that connect you seamlessly to the city. If you're looking for an urban oasis that combines both prestige and practicality, this is it. Dont miss out on this rare find its the perfect place to call home. EXTRAS: Experience the luxury of South Hill on Madison Condos, offering a range of premium amenities such as a fitness center, rooftop lounge with stunning views, private parking, and secure access for ultimate convenience and comfort. More details
    Listed by HARVEY KALLES REAL ESTATE LTD.
    LISTING DETAILS

  • 403 159 Russell Hill Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12341903

    403 159 Russell Hill Road Casa Loma Toronto M4V 2S9
    Main Photo: 403 159 Russell Hill Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12341903

    403 159 Russell Hill Road Toronto M4V 2S9 Casa Loma

    $3,200
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C12341903
    Bedrooms:
    2
    Bathrooms:
    2
    Welcome To This Intimate Low Rise Building In The Heart Of South Hill!! Surrounded By Incredible Mansions All Around You! Located Steps To Incredible Amenities Like Winston Churchill Park And Ravine System, Lrt Streetcars, Both Bathurst And Yonge/St Clair Subways, Forest Hill Village, Yonge/St Clair Shops And Restaurants And The Best Public And Private Schools In Toronto! These Suites Offer Wood Flooring, Newer Appliances, Balconies And Large Open Concept Space! Units Are Available For Immediate Occupancy. *12th Month is Free on a 2-Year Lease* More details
    Listed by RE/MAX HALLMARK BATORI GROUP INC.
    LISTING DETAILS

  • 303 221 Russell Hill Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12341958

    303 221 Russell Hill Road Casa Loma Toronto M4V 2S9
    Main Photo: 303 221 Russell Hill Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12341958

    303 221 Russell Hill Road Toronto M4V 2S9 Casa Loma

    $3,200
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C12341958
    Bedrooms:
    2
    Bathrooms:
    2
    Welcome To This Intimate Low Rise Building In The Heart Of South Hill!! Surrounded By Incredible Mansions All Around You! LocatedSteps To Incredible Amenities Like Winston Churchill Park And Ravine System, Lrt Streetcars, Both Bathurst And Yonge/St Clair Subways, Forest HillVillage, Yonge/St Clair Shops And Restaurants And The Best Public And Private Schools In Toronto! These Suites Offer Wood Flooring, NewerAppliances, Balconies And Large Open Concept Space! Units Are Available For Immediate Occupancy. **12th Month is Free on a 2-Year Lease** More details
    Listed by RE/MAX HALLMARK BATORI GROUP INC.
    LISTING DETAILS

  • 129 1 Benvenuto Place in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C12336794

    129 1 Benvenuto Place Casa Loma Toronto M4V 2L1
    Main Photo: 129 1 Benvenuto Place in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C12336794

    129 1 Benvenuto Place Toronto M4V 2L1 Casa Loma

    $999,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C12336794
    Bedrooms:
    2
    Bathrooms:
    1
    Sophisticated and serene main-level suite in the emblamatic Benvenuto. This beautifully redesigned 1-bedroom plus den residence offers 956 sq. ft. of refined living, with no need for elevators simply valet your car & walk right in from the main floor for ultimate ease and privacy. Thoughtfully renovated to enhance functionality and flow, the kitchen has been expanded and features a large island, marble countertops, and a clean, modern layout ideal for entertaining. Wide-plank white oak herringbone flooring runs throughout the space, adding timeless elegance. The spa-inspired bathroom is generously sized, with striking hexagon tile, a seamless glass shower equipped with full body jets and a rain shower head, plus a large double-sink vanity with excellent storage. The bedroom includes custom wall panelling, a smartly designed walk-in closet and semi-ensuite access to the bath. A separate den, accessible through sliding doors, offers a flexible space for a home office or reading nook. West-facing exposure brings in soft afternoon light, complementing features like the custom built-ins throughout, custom built ins in the living room and den w/lighting, and remote controlled blinds. Enjoy the comfort and security of valet parking and the prestige of living in a mid-century architectural gem also home to the celebrated Scaramouche Restaurant. An ideal choice for those looking to downsize in style or enjoy a turnkey pied-a-terre with unmatched convenience. More details
    Listed by FOREST HILL REAL ESTATE INC.
    LISTING DETAILS

  • 8 223 St Clair Avenue W in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12336357

    8 223 St Clair Avenue W Casa Loma Toronto M4V 0A5
    Main Photo: 8 223 St Clair Avenue W in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12336357

    8 223 St Clair Avenue W Toronto M4V 0A5 Casa Loma

    $3,300
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C12336357
    Bedrooms:
    2
    Bathrooms:
    2
    Stylish 2-Bed, 2-Bath at Zigg Condos!797 sq. ft. plus balcony with west views, parking & large locker. Smooth ceilings, radiant in-floor heating, steps to St. Clair Station, shops & dining. Luxury amenities: rooftop terrace w/ BBQ, concierge, fitness, billiards & more. More details
    Listed by RARE REAL ESTATE
    LISTING DETAILS

  • 418 396 Avenue Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12335784

    418 396 Avenue Road Casa Loma Toronto M4V 2H5
    Main Photo: 418 396 Avenue Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12335784

    418 396 Avenue Road Toronto M4V 2H5 Casa Loma

    $2,150
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C12335784
    Bedrooms:
    1
    Bathrooms:
    1
    ***One month free rent*** 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. More details
    Listed by RE/MAX REALTRON REALTY INC.
    LISTING DETAILS

  • 105 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12331298

    105 377 Madison Avenue Casa Loma Toronto M4V 3E1
    Main Photo: 105 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12331298

    105 377 Madison Avenue Toronto M4V 3E1 Casa Loma

    $2,700
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C12331298
    Bedrooms:
    2
    Bathrooms:
    2
    Luxury Unit On Casa Loma Area. Amazing Location Close To Forest Hill. Annex, Close To Davenport T.T.C. This Unit Is Bright, Spacious And Has A Open Concept Layout. Also Has 9 Ft Ceiling With Large Master Bedroom And Den That Can Be Used As A Office Or Dining Area. 1 Parking. Excellent Amenities Such As Visitor Parking, Gym, Party Room, Media Room, Pet Spa, Yoga Studio, Etc. Concierge. Also All Amenities Included 24 hours. More details
    Listed by ROYAL LEPAGE TERREQUITY REALTY
    LISTING DETAILS

  • 5 300 Avenue Road in Toronto: Casa Loma Condo Townhouse for sale (Toronto C02) : MLS®# C12329693

    5 300 Avenue Road Casa Loma Toronto M4V 2H1
    Main Photo: 5 300 Avenue Road in Toronto: Casa Loma Condo Townhouse for sale (Toronto C02) : MLS®# C12329693

    5 300 Avenue Road Toronto M4V 2H1 Casa Loma

    $1,345,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C12329693
    Bedrooms:
    3
    Bathrooms:
    2
    Live in timeless elegance at 300 Avenue Rd a boutique, upgraded 2+1 bedroom residence nestled in one of Torontos most prestigious and charming neighbourhoods. Set within a converted heritage building, this one-of-a-kind home blends classic character with contemporary luxury. Featuring exquisite herringbone hardwood floors, a private in-suite sauna, and thoughtfully designed interiors with custom millwork and premium finishes throughout, every detail reflects refined craftsmanship. The open-concept living and dining area is perfect for entertaining, while the versatile den serves as a home office, reading nook, or guest retreat. Just steps to Yorkville, Summerhill, and Casa Loma, with top-tier dining, shops, and transit at your doorstep this rare offering delivers boutique living with big city convenience. A true gem for those who value style, comfort, and location. More details
    Listed by PROPERTY.CA INC.
    LISTING DETAILS

  • 317 380 Macpherson Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C12323572

    317 380 Macpherson Avenue Casa Loma Toronto M4V 3E3
    Main Photo: 317 380 Macpherson Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C12323572

    317 380 Macpherson Avenue Toronto M4V 3E3 Casa Loma

    $859,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C12323572
    Bedrooms:
    2
    Bathrooms:
    1
    Experience sophisticated urban living in this stunning loft-style suite located in the iconic Madison Avenue Lofts in one of Toronto's most sought-after neighbourhoods just south of Casa Loma. This spacious unit has been thoughtfully updated with a new kitchen, custom island and high-end flooring throughout. Enjoy the semi-ensuite bathroom and peaceful bedroom retreat with space for a King-size bed and the large closet. The versatile floorplan includes a tucked-away Den, ideal for a home office or enclose it to create a nursery or private retreat for weekend guests. With soaring 12-foot ceilings, exposed concrete, ductwork and expansive windows, this loft offers a chic, industrial aesthetic combined with modern comfort. Enjoy two west-facing balconies that overlook the quiet, inner courtyard, creating a sense of tranquility in the heart of the city. Amenities in this exceptional lifestyle building include 24-hour concierge, rooftop terrace with BBQs, fully equipped gym, steam sauna, theatre & party room. A 5-minute walk to Dupont Subway Station, steps from George Brown College, University of Toronto, and the vibrant neighbourhoods of The Annex, Yorkville, and Forest Hill Village can be enjoyed with the 95 Walk and Bike Score to local shopping, dining, and the newly revitalized Dupont strip. Underground parking spot, locker and Unlimited Bell Fibe internet included? You bet. Make 380 Macpherson your next move. More details
    Listed by SAGE REAL ESTATE LIMITED
    LISTING DETAILS

  • 321 1 Benvenuto Place in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C12324657

    321 1 Benvenuto Place Casa Loma Toronto M4V 2L1
    Main Photo: 321 1 Benvenuto Place in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C12324657

    321 1 Benvenuto Place Toronto M4V 2L1 Casa Loma

    $2,795,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C12324657
    Bedrooms:
    3
    Bathrooms:
    3
    Direct from the developer and brand new and fully renovated with taste and panache. This is refined living at The Benvenuto. This light-filled 2,209 square foot 2 bedroom plus den, 2.5 bathroom suite showcases top-tier finishes highlighted with rich, warm walnut flooring that flows seamlessly throughout. The phenomenal layout encompasses a spacious open concept living, dining, and den area, perfect for both entertaining and everyday living. The oversized gourmet eat-in kitchen, designed by Bellini, features a substantial centre island with breakfast bar, dinette area, and superb appliances. "Patton Design" selected upscale, transitional interior finishes to create a sophisticated backdrop for your personal style. The suite is complemented by 2.5 luxuriously appointed bathrooms. Suite 321, is positioned advantageously three stories above the slope of the hill, offering a treetop perspective, providing elevated views of the historic gothic mansion at De La Salle College with mature trees in the distance. This full-service building offers valet parking, a full-time concierge plus a day porter, on-site management and superintendent personnel, a glass gym on the rooftop, two (valet) parking spaces and a locker. Located in the exclusive residential pocket near Avenue Road and St Clair, this mid-century modern masterpiece of a building is exceptionally well maintained and heritage designated. Your tastebuds will be tempted at Scaramouche, on the ground floor. One of Toronto's most illustrious restaurants. You'll adore living at The Benvenuto. More details
    Listed by SOTHEBY'S INTERNATIONAL REALTY CANADA
    LISTING DETAILS
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Data was last updated August 15, 2025 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.