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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  • 101 394 Avenue Road in Toronto: Casa Loma Condo for lease (Toronto C02) : MLS®# C9393214

    101 394 Avenue Road Casa Loma Toronto M4V 2H4
    Main Photo: 101 394 Avenue Road in Toronto: Casa Loma Condo for lease (Toronto C02) : MLS®# C9393214

    101 394 Avenue Road Toronto M4V 2H4 Casa Loma

    $1,795
    Condo
    Status:
    For Lease
    MLS® Num:
    C9393214
    Bathrooms:
    1
    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

  • 517 396 Avenue Road in Toronto: Casa Loma Condo for lease (Toronto C02) : MLS®# C9392797

    517 396 Avenue Road Casa Loma Toronto M4V 2H5
    Main Photo: 517 396 Avenue Road in Toronto: Casa Loma Condo for lease (Toronto C02) : MLS®# C9392797

    517 396 Avenue Road Toronto M4V 2H5 Casa Loma

    $1,795
    Condo
    Status:
    For Lease
    MLS® Num:
    C9392797
    Bathrooms:
    1
    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

  • 38 Poplar Plains Crescent in Toronto: Casa Loma House (2 1/2 Storey) for sale (Toronto C02) : MLS®# C9389603

    38 Poplar Plains Crescent Casa Loma Toronto M4V 1E8
    Main Photo: 38 Poplar Plains Crescent in Toronto: Casa Loma House (2 1/2 Storey) for sale (Toronto C02) : MLS®# C9389603

    38 Poplar Plains Crescent Toronto M4V 1E8 Casa Loma

    $2,725,000
    Freehold
    Status:
    Active
    MLS® Num:
    C9389603
    Bedrooms:
    3
    Bathrooms:
    3
    A detached gem in the heart of a top family-friendly neighbourhood, Rathnelly. Beautifully renovated 3 bedroom, with 30' frontage and two car parking with garage. Low traffic quiet crescent surrounded by significant neighbours and in a historic and storied enclave. Charming period details such as leaded and stained glass windows with contemporary touches. Wonderful chef's kitchen with extra large eat-in area, large farmers sink, double wall ovens, and extra large kitchen island that seats four. French double doors lead to peaceful lush green ravine views on the low-maintenance garden terrace off the kitchen. Cozy wood burning fireplace in the living room with abundant south light. Generous primary bedroom with large sitting area or office and great walk-in closet. A second bedroom on the second floor has dramatic city skyline views and custom millwork. A third bedroom on the third floor is an ideal teen suite or even a mediation area. Newly renovated bright basement with wonderful laundry area. Toronto's top private and public schools are within walking distance. More details
    Listed by CHESTNUT PARK REAL ESTATE LIMITED
    LISTING DETAILS

  • 203 195 Poplar Plains Road in Toronto: Casa Loma Condo for sale (Toronto C02) : MLS®# C9388688

    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®# C9388688

    203 195 Poplar Plains Road Toronto M4V 2N3 Casa Loma

    $1,524,999
    Condo
    Status:
    Active
    MLS® Num:
    C9388688
    Bedrooms:
    1
    Bathrooms:
    2
    Step into timeless elegance and modern sophistication in this two-level condo, nestled within a restored mansion in Toronto's exclusive South Hill. This pied--terre offers a blend of historic charm and contemporary luxury.The main level features a newly renovated, chef-inspired kitchen with high-end appliances, perfect for gourmet dining. The spacious living area, complete with a cozy fireplace, creates an inviting space for relaxation and entertaining. Upstairs, the second-floor retreat includes a spa-like bathroom with skylight and a luxurious bedroom sanctuary with vaulted ceilings. Work from home, and take a break on your private deck to enjoy the neighbourhood charm. Set in a classic building with just six architecturally designed suites, Condo 203 provides privacy, prestige, and tranquility. Located moments from Yorkville's fine dining and Sir Winston Churchill Park, this home offers the perfect blend of city living and peaceful retreat, tailored to a discerning lifestyle. More details
    Listed by ENGEL & VOLKERS TORONTO CENTRAL
    LISTING DETAILS

  • 110 2 Clarendon Avenue in Toronto: Casa Loma Condo for lease (Toronto C02) : MLS®# C9388483

    110 2 Clarendon Avenue Casa Loma Toronto M4V 1H9
    Main Photo: 110 2 Clarendon Avenue in Toronto: Casa Loma Condo for lease (Toronto C02) : MLS®# C9388483

    110 2 Clarendon Avenue Toronto M4V 1H9 Casa Loma

    $2,995
    Condo
    Status:
    For Lease
    MLS® Num:
    C9388483
    Bedrooms:
    1
    Bathrooms:
    1
    ** One Month FREE *** This is a MUST SEE S1 Bedrooms in stunning restored building. From the walnut hardwood floor, to the kitchen with oversized fridge, gorgeous wall paneling, large bedrooms with plenty of custom closet space and modern bathroom, THIS is the place to call home and to live and entertain with sophistication and style. **Two Clarendon Avenue** stands as a beacon of refined luxury in the heart of Forest Hill, Toronto's most prestigious enclave. 1 Bedroom Apartment. Perfect for busy professional or student. This distinguished heritage building, dating back to the 1920s, has been meticulously restored and modernized, marrying historical grandeur with contemporary opulence. Each suite exudes sophistication, featuring exquisite wood floors and stunning granite countertops. The bathrooms, redesigned with elegance in mind, boast the latest fixtures and fittings, complemented by completely updated plumbing, electrical, and heating systems. The heritage lobby has been preserved, maintaining its original charm, while the newly added common spaces reflect a seamless blend of tradition and modernity. A Legacy of Luxury Living. Two Clarendon Avenue is more than just a residence; it is a sanctuary of timeless elegance and modern convenience. Every detail has been meticulously curated to provide an unparalleled living experience in one of the city's most coveted locations. Embrace the legacy and live in the epitome of luxury at Two Clarendon Avenue. More details
    Listed by CITY REALTY POINT
    LISTING DETAILS

  • 210 2 Clarendon Avenue in Toronto: Casa Loma Condo for lease (Toronto C02) : MLS®# C9388490

    210 2 Clarendon Avenue Casa Loma Toronto M4V 1H9
    Main Photo: 210 2 Clarendon Avenue in Toronto: Casa Loma Condo for lease (Toronto C02) : MLS®# C9388490

    210 2 Clarendon Avenue Toronto M4V 1H9 Casa Loma

    $7,350
    Condo
    Status:
    For Lease
    MLS® Num:
    C9388490
    Bedrooms:
    2
    Bathrooms:
    2
    ** One Month FREE *** This is a MUST SEE THIS 2 Bedrooms 2 Bathrooms 1,339 sq ft. in stunning restored building. From the walnut hardwood floor, to the kitchen with oversized fridge, gorgeous wall paneling, large bedrooms with plenty of custom closet space and modern bathroom, THIS is the place to call home and to live and entertain with sophistication and style. **Two Clarendon Avenue** stands as a beacon of refined luxury in the heart of Forest Hill, Toronto's most prestigious enclave. 2 Bedroom Apartment. Perfect for busy professionals, Families. This distinguished heritage building, dating back to the 1920s, has been meticulously restored and modernized, marrying historical grandeur with contemporary opulence. Each suite exudes sophistication, featuring exquisite wood floors and stunning granite countertops. The bathrooms, redesigned with elegance in mind, boast the latest fixtures and fittings, complemented by completely updated plumbing, electrical, and heating systems. The heritage lobby has been preserved, maintaining its original charm, while the newly added common spaces reflect a seamless blend of tradition and modernity. A Legacy of Luxury Living. Two Clarendon Avenue is more than just a residence; it is a sanctuary of timeless elegance and modern convenience. Every detail has been meticulously curated to provide an unparalleled living experience in one of the city's most coveted locations. Embrace the legacy and live in the epitome of luxury at Two Clarendon Avenue. More details
    Listed by CITY REALTY POINT
    LISTING DETAILS

  • 607 223 St Clair Avenue W in Toronto: Casa Loma Condo for lease (Toronto C02) : MLS®# C9386476

    607 223 St Clair Avenue W Casa Loma Toronto M4V 1R3
    Main Photo: 607 223 St Clair Avenue W in Toronto: Casa Loma Condo for lease (Toronto C02) : MLS®# C9386476

    607 223 St Clair Avenue W Toronto M4V 1R3 Casa Loma

    $2,500
    Condo
    Status:
    For Lease
    MLS® Num:
    C9386476
    Bedrooms:
    2
    Bathrooms:
    1
    Zigg Condos! Contemporary & Upscale 1Bed + Den, 615 Sqft Unit Developed By The Prestigious Madison Group In The Forest Hill Neighborhood. Easy Access To Shopping, Restaurants, Ttc & St. Clair Station. Building Amenities Include An Executive Concierge, Rooftop Terrace With Bbq Area, Fireplace, Indoor Bar, Private Fitness Centre, Billiards Room, Dining Room, Complimentary Guest Wi-Fi, & Pet-Washing Station! 1 Parking More details
    Listed by HOMELIFE LANDMARK REALTY INC.
    LISTING DETAILS

  • 523 377 Madison Avenue in Toronto: Casa Loma Condo for lease (Toronto C02) : MLS®# C9385582

    523 377 Madison Avenue Casa Loma Toronto M4V 2W7
    Main Photo: 523 377 Madison Avenue in Toronto: Casa Loma Condo for lease (Toronto C02) : MLS®# C9385582

    523 377 Madison Avenue Toronto M4V 2W7 Casa Loma

    $2,200
    Condo
    Status:
    For Lease
    MLS® Num:
    C9385582
    Bedrooms:
    1
    Bathrooms:
    1
    Welcome to boutique living nestled in the Casa Loma area. This junior one bedroom features a functional layout, bright and charming with modern kitchen. Conveniently accessible to everything - Dupont Station, nature, Casa Loma, U of T, George Brown, Forest Hill, Annex, Yorkville, shops, cafes & more! Stunning boutique building with amenities including gym, yoga studio, pet spa and concierge. More details
    Listed by IPRO REALTY LTD.
    LISTING DETAILS

  • 432 380 Macpherson Avenue in Toronto: Casa Loma Condo for sale (Toronto C02) : MLS®# C9383890

    432 380 Macpherson Avenue Casa Loma Toronto M4V 3E3
    Main Photo: 432 380 Macpherson Avenue in Toronto: Casa Loma Condo for sale (Toronto C02) : MLS®# C9383890

    432 380 Macpherson Avenue Toronto M4V 3E3 Casa Loma

    $399,000
    Condo
    Status:
    Active
    MLS® Num:
    C9383890
    Bedrooms:
    1
    Bathrooms:
    1
    This loft-style bachelor apartment, nestled in the heart of the refined and highly sought-after Casa Loma neighbourhood, boasts 14-foot ceilings with exposed ductwork, creating a modern, industrial loft aesthetic. The sun-soaked living space is enhanced by a cozy electric fireplace, while the tall walls provide the perfect canvas for showcasing your most cherished art pieces. The open-concept kitchen features sleek granite countertops and abundant cupboard space. Enjoy an elevated private bedroom loft, ideal for young professionals seeking a chic lifestyle in one of Toronto's best neighbourhood! Located just steps from Yorkville, The Annex, George Brown College, UofT, and Dupont Subway Station! This exclusive building offers top-tier amenities including a 24-hour concierge, a stunning rooftop deck with BBQs, a fitness room/gym, steam saunas, visitor parking, & guest suites. The perfect condo for a young professional who is looking to settle into a mature & prestigious community! More details
    Listed by KELLER WILLIAMS REFERRED URBAN REALTY
    LISTING DETAILS

  • 26 Mcmaster Avenue in Toronto: Casa Loma House (3-Storey) for sale (Toronto C02) : MLS®# C9383422

    26 Mcmaster Avenue Casa Loma Toronto M4V 1A9
    Main Photo: 26 Mcmaster Avenue in Toronto: Casa Loma House (3-Storey) for sale (Toronto C02) : MLS®# C9383422

    26 Mcmaster Avenue Toronto M4V 1A9 Casa Loma

    $4,343,000
    Freehold
    Status:
    Active
    MLS® Num:
    C9383422
    Bedrooms:
    4
    Bathrooms:
    5
    Welcome to this gorgeous, detached red brick home in coveted Republic of Rathnelly. Undergoing a stunning renovation, the space has been completely reimagined for todays modern family. The epitome of luxury, featuring quality finishes & the finest workmanship throughout, this warm & inviting hm is absolute perfection. An open concept main floor starts from the welcoming foyer & leads to an oversized living / dining rm which is ideal for entertaining. To the side, the perfectly tucked away family rm provides a cozy retreat w a gas f/pl. Pass through the pantry/bar to the designer kitchen w/ an oversized island, high end appliances & enjoy the natural light that streams in thru the rear windows & door. 3 generously sized bedrms on the 2nd floor & gorgeously renovated bathrms & the Primary oasis has an incredible walk-in closet, tasteful built-ins, a 6-pc spa-like en suite w/ a lg window providing amazing daylight & a fabulous terrace o/looking the garden oasis. The 2nd bedrm has additional office space perfect for WFH or is a great homework space or den. The 3rd floor is an open concept family rm w/ a great laundry room, kitchenette & 3pc bath ensuring the space can be used in multiple ways. The huge 3rd floor balcony is the perfect place to relax & recharge on natures own Vitamin D. Living in the heart of Rathnelly creates instant community w/ wonderful neighbours on an incredibly quiet street where parking abounds. Seldom does a home this thoughtfully designed come to market. Maintenance free urban zen garden & detached 2-car garage off the rear lane is a dream. Easy walkability to Yorkville, Av & Dav, Parks and Ravine Trails, Mabin, York, DeLaSalle, U.C.C., R.S.G.C, & top-rated Brown PS is a AAA+ location. This premium location is where everyone wants to be and this exciting & contemporary home w/ exceptional design is a rare one-of-a-kind offering! More details
    Listed by ROYAL LEPAGE REAL ESTATE SERVICES OXLEY REAL ESTATE
    LISTING DETAILS

  • 405 380 Macpherson Avenue in Toronto: Casa Loma Condo for lease (Toronto C02) : MLS®# C9380042

    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®# C9380042

    405 380 Macpherson Avenue Toronto M4V 3E3 Casa Loma

    $4,490
    Condo
    Status:
    For Lease
    MLS® Num:
    C9380042
    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 ROYAL LEPAGE REAL ESTATE SERVICES LTD.
    LISTING DETAILS

  • 202 380 Macpherson Avenue in Toronto: Casa Loma Condo for sale (Toronto C02) : MLS®# C9380442

    202 380 Macpherson Avenue Casa Loma Toronto M4V 3E3
    Main Photo: 202 380 Macpherson Avenue in Toronto: Casa Loma Condo for sale (Toronto C02) : MLS®# C9380442

    202 380 Macpherson Avenue Toronto M4V 3E3 Casa Loma

    $989,000
    Condo
    Status:
    Active
    MLS® Num:
    C9380442
    Bedrooms:
    2
    Bathrooms:
    2
    Live in one of Toronto's most well-appointed lofts, the Madison Avenue Lofts. This 2-Bedroom, 2-Bath, 930 Sq. Ft. Suite + 65 Sq. Ft. Balcony Boasts 14 ft Soaring Ceiling heights, Bright Dramatic Floor to Ceiling Windows Streaming Loads of Natural Sunlight. Modern U-Shaped Kitchen with Breakfast Bar, New Quartz Countertops and New Backsplash. Bathrooms with Stone Countertops. Generous Closet Space with Custom Closet Organizers. Steps to Casa Loma, George Brown College, Dupont Subway Station, Restaurants, etc. Shows to Perfection! More details
    Listed by FOREST HILL REAL ESTATE INC.
    LISTING DETAILS
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Data was last updated October 13, 2024 at 11:55 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 Toronto Regional Real Estate Board. The data is deemed reliable but is not guaranteed to be accurate.
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