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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  • 1 Glen Edyth Place in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C13452154

    1 Glen Edyth Place Casa Loma Toronto M4V 2W1
    Main Photo: 1 Glen Edyth Place in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C13452154

    1 Glen Edyth Place Toronto M4V 2W1 Casa Loma

    $8,950,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C13452154
    Bedrooms:
    5
    Bathrooms:
    6
    Tucked within one of South Hill's most exclusive and private enclaves. This is the last great lot on Glen Edyth Pl. This exceptional residence offers a rare opportunity to own a true family home in an unparalleled setting. Situated on a coveted cul-de-sac, the property combines the serenity of a secluded retreat with effortless access to the city's core. Designed with both scale and comfort in mind, the home features over 7000sqft of living space, with four well-appointed bedrooms and beautifully proportioned principal rooms that lend themselves to both everyday living and elegant entertaining. Soaring ceilings and expansive windows fill the interiors with natural light, creating a warm yet sophisticated atmosphere throughout. At the heart of the home, the kitchen and adjoining family room offer a seamless space for gathering, while the primary suite provides a quiet, private retreat. The lower level includes a large recreation room for entertaining and an additional bedroom, perfect for in-laws or guests. Every element has been thoughtfully considered to balance function with refined design. Set on an extraordinary lot, the outdoor space feels worlds away from the city, with mature landscaping, complete privacy, and a stunning pool that transforms the backyard into a true oasis. The lower level further enhances the home's livability, offering additional space for relaxation, recreation, or extended family use. A rare offering in South Hill for those seeking privacy, scale, and an address defined by both prestige and quiet exclusivity. More details
    Listed by CHESTNUT PARK REAL ESTATE LIMITED
    LISTING DETAILS

  • 319 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13445122

    319 377 Madison Avenue Casa Loma Toronto M4V 3E1
    Main Photo: 319 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13445122

    319 377 Madison Avenue Toronto M4V 3E1 Casa Loma

    $3,200
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C13445122
    Bedrooms:
    2
    Bathrooms:
    2
    Nestled at the base of the majestic Casa Loma, South Hill on Madison lets you enjoy the best of both world's: serene surroundings and easy access to the city's vibrant core. This spacious 2bedroom, 2 bathroom condo offers almost 900 SF of living space. It features laminate flooring throughout & 9-Ft smooth ceilings. The chic kitchen features white quartz countertops, an undermount sink & an abundance of cabinet space for all your storage needs. The versatile island doubles as a breakfast bar, perfect for casual dining or extra prep space. High-end stainless steel built-in appliances complete the kitchen. Plus, enjoy the convenience of ensuite laundry and a locker for extra storage space. Building amenities include a fully-equipped gym, yoga studio, party room, rooftop deck & concierge. Located just a short 5-7minute walk to Dupont Subway Station, commuting to the city's vibrant core is a breeze, while the tranquil Casa Loma neighborhood provides a peaceful retreat. Live in one of Toronto's most desirable and picturesque locations! Parking and locker is included. More details
    Listed by ROYAL LEPAGE SIGNATURE REALTY
    LISTING DETAILS

  • 109 235 St Clair Avenue W in Toronto: Casa Loma Commercial for lease (Toronto C02) : MLS®# C13444372

    109 235 St Clair Avenue W Casa Loma Toronto M4V 1R4
    Main Photo: 109 235 St Clair Avenue W in Toronto: Casa Loma Commercial for lease (Toronto C02) : MLS®# C13444372

    109 235 St Clair Avenue W Toronto M4V 1R4 Casa Loma

    $4,000 /Month
    Commercial
    Status:
    For Lease
    MLS® Num:
    C13444372
    Major Bus.:
    Professional Office
    Total Area:
    745 sq. ft.
    Prime Commercial Medical Clinic Opportunity! Rarely available, this recently renovated main-floor commercial condominium is located in one of Toronto's most sought-after neighbourhoods. Situated within an exclusive 5-storey boutique building comprised primarily of residential suites, this bright and professionally designed space offers direct street-level access through a private entrance with no elevator required.Featuring floor-to-ceiling north-facing windows, the unit is filled with natural light and offers a functional layout including a welcoming reception/waiting area, four examination or treatment rooms, two washrooms, and a spacious private balcony. Previously occupied by a successful orthodontic practice, the space is ideally suited for a variety of medical and healthcare professionals.Permitted uses include Medical Doctor (MD), Specialist Clinic, Dental Practice, Orthodontic Clinic, Chiropractic Clinic, Medical Aesthetics, and other approved healthcare-related uses. One underground parking space is included for exclusive use.Conveniently located directly on TTC transit routes and just minutes from Yonge Street, this exceptional location is surrounded by established residential communities, boutique shops, cafés, restaurants, professional services, and parks. A rare opportunity to establish or expand your practice in a prestigious Toronto neighbourhood with excellent accessibility and strong local demographics. More details
    Listed by RIGHT AT HOME REALTY
    LISTING DETAILS

  • 523 398 Avenue Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13436568

    523 398 Avenue Road Casa Loma Toronto M4V 2H4
    Main Photo: 523 398 Avenue Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13436568

    523 398 Avenue Road Toronto M4V 2H4 Casa Loma

    $1,950
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C13436568
    Bedrooms:
    1
    Bathrooms:
    1
    *** TWO FREE MONTHS on a 2-year lease or ONE MONTH FREE on a 1-year lease ***PLUS $1000 credit in the 3rd month***Very Quick move-ins Students, Professionals, and Newcomers welcome*** Rent-controlled building *** Utilities included (heat, hydro, water) ***Situated in prestigious Forest Hill in the heart of the city, this charming building offers a blend of character suites and excellent rental value. Just minutes from shopping, restaurants, transit, and close to popular areas such as The Annex, Yorkville, and the downtown financial district.Newly renovated units feature updated appliances and hardwood flooring throughout. On-site laundry facilities available. A trendy bistro and convenient store are located in the adjacent building. Utilities included (heat, water, hydro); portable A/C units permitted. More details
    Listed by ROYAL LEPAGE SIGNATURE REALTY
    LISTING DETAILS

  • 324 380 Macpherson Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13429026

    324 380 Macpherson Avenue Casa Loma Toronto M4V 3E3
    Main Photo: 324 380 Macpherson Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13429026

    324 380 Macpherson Avenue Toronto M4V 3E3 Casa Loma

    $3,000
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C13429026
    Bedrooms:
    1
    Bathrooms:
    1
    Authentic hard loft living at Madison Avenue Lofts! This rarely available 816 sq. ft. suite is located in one of Toronto's most sought-after boutique buildings and includes parking and locker. Featuring soaring 12-foot ceilings, exposed ductwork, oversized industrial-style windows, and an airy open-concept layout flooded with natural light. Enjoy peaceful treetop views from the oversized windows, creating a private and serene atmosphere rarely found in the views from the oversized windows, creating a private and serene atmosphere rarely found in the city. The spacious living and dining area offers plenty of room to entertain, while the versatile den is ideal for a home office, reading nook, or creative workspace. The generous bedroom offers excellent storage, and the updated flooring and bathroom give the suite a fresh, contemporary feel. Take in stunning views of Casa Loma from the rooftop terrace, the perfect spot to unwind or entertain. Located steps to Dupont Station, Casa Loma, Yorkville, The Annex, parks, cafés, restaurants, and Bloor Street shopping. Available immediately! More details
    Listed by ROYAL LEPAGE TERREQUITY SW REALTY
    LISTING DETAILS

  • 318 377 Madison Avenue in Toronto: Casa Loma Condo for lease (Toronto C02) : MLS®# C13427798

    318 377 Madison Avenue Casa Loma Toronto M4V 3E1
    Main Photo: 318 377 Madison Avenue in Toronto: Casa Loma Condo for lease (Toronto C02) : MLS®# C13427798

    318 377 Madison Avenue Toronto M4V 3E1 Casa Loma

    $2,650
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C13427798
    Bedrooms:
    1
    Bathrooms:
    1
    Welcome To South Hill On Madison - A Contemporary Art Deco Condominium Located At The Foot Of Casa Loma, Where Forest Hill Meets The Annex. An Exquisite Boutique Building In A Quiet Residential Setting. The Very Best 1 Bedroom + Den Layout Of Only 4 In The Entire Building. 170 Square Foot Terrace. This Unit Boasts Open Concept Living For Comfort And Entertaining. The Unit Comes Complete With Underground Parking. This Enviable Mid-Town Location Is Only Steps To The Vibrant Dupont Strip With Its Restaurant's, Shops And TTC Subway Station. This Building Provides, 24 Hour Concierge, Gym, Party Room, and Theatre Room. For the convenience of extra storage the unit comes with a storage locker. More details
    Listed by PSR
    LISTING DETAILS

  • 507 394 Avenue Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13424402

    507 394 Avenue Road Casa Loma Toronto M4V 2H4
    Main Photo: 507 394 Avenue Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13424402

    507 394 Avenue Road Toronto M4V 2H4 Casa Loma

    $2,095
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C13424402
    Bedrooms:
    1
    Bathrooms:
    1
    SAVE MONEY! | UpTo 2 MONTHS FREE* | ADDITIONAL $1000 credit in the 3rd month | Move-In This Week | Spacious 1-bedroom unit at Mayfair Mansions in the prestigious Forest Hill neighbourhood. This charming building combines character and modern updates, offering spacious suites with hardwood flooring, updated appliances including fridge, stove, microwave, and dishwasher, and a large living area filled with natural light. Each unit includes a private balcony. Building amenities include smart-card laundry facilities, on-site superintendent, secure camera-monitored entry, elevator service, and optional indoor parking ($250-$275/month). Steps from shopping, restaurants, transit, and minutes from The Annex, Yorkville, and downtown Toronto, this location provides a walk score over 90. Ideal for professionals or couples seeking a move-in-ready, low-maintenance suite in a stylish, central location. More details
    Listed by CITY REALTY POINT
    LISTING DETAILS

  • 236 Poplar Plains Road in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C13422222

    236 Poplar Plains Road Casa Loma Toronto M4V 2N7
    Main Photo: 236 Poplar Plains Road in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C13422222

    236 Poplar Plains Road Toronto M4V 2N7 Casa Loma

    $6,495,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C13422222
    Bedrooms:
    5
    Bathrooms:
    5
    Hidden entirely behind a mature wall of hedges on one of South Hill's most coveted streets, this private residence on Poplar Plains Road pairs the formal pedigree of Georgian Revival with the romance of a European garden estate, offering a rare combination of scale, seclusion, and Old World character on an oversized 79.65 x 110 ft lot. A gated stone walkway leads to a grand arrival, where a classical pedimented portico framed by columns opens to a gracious foyer and sweeping main hall staircase. Inside, 6,464 square feet of stately living space unfolds with soaring ceilings, solid hardwood floors, leaded glass windows, and original detailing throughout. A formal living room with wood-burning fireplace walks out to a serene covered veranda, while the panelled formal dining room, anchored by its own fireplace, holds a true sense of occasion. At the heart of the home, a chef-calibre kitchen with honed Calacatta counters and framed cabinetry opens to a warm family room. The second floor is anchored by an elegant primary suite with a beautifully appointed ensuite, alongside two additional well-proportioned bedrooms, while the third floor offers two further bedrooms and a private retreat with office, den, and family room warmed by a gas fireplace. The lower level is dedicated to lifestyle, with a home gym and wine cellar. Outside, a covered veranda with terracotta floors overlooks a professionally landscaped garden wrapped entirely in greenery, framed by mature hedges and Japanese maples - a private oasis with the romance of a European country estate and a storybook garden chalet. Moments from Winston Churchill Park, the shops and restaurants of Yonge & St. Clair, and Toronto's most respected public and private schools, this is a setting families hold for generations. Private viewings by appointment. Virtual tour link has additional photos. More details
    Listed by SOTHEBY'S INTERNATIONAL REALTY CANADA
    LISTING DETAILS

  • 1106 223 St Clair Avenue W in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C13415086

    1106 223 St Clair Avenue W Casa Loma Toronto M4V 0A5
    Main Photo: 1106 223 St Clair Avenue W in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C13415086

    1106 223 St Clair Avenue W Toronto M4V 0A5 Casa Loma

    $999,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C13415086
    Bedrooms:
    3
    Bathrooms:
    2
    Suite 1106 at Zigg Condos is a rare NE corner suite featuring a split 3-bedroom floor plan and 999 sq ft of smartly designed living in the heart of Midtown Toronto. Set on the 11th floor with light and views from two directions, this home feels bright, private, and beautifully proportioned from the moment you walk in. The split bedroom layout is the magic. The primary suite sits on one side of the home, while two additional bedrooms are thoughtfully positioned on the other - ideal for children, guests, a home office, or simply the extra space that modern life demands. Two full bathrooms, 9-foot ceilings, brand-new flooring, and fresh paint throughout add comfort, style, and everyday ease. The kitchen is chic and functional, opening into a generous living and dining area that feels calm, airy, and easy to furnish. Some photos have been virtually staged to help show the suite's potential and how beautifully the space can live. Step out to the balcony for fresh air and open Midtown views - a lovely reminder of why Midtown living is so appealing. Zigg Condos offers the boutique feel buyers love, with only 166 suites and a thoughtful collection of amenities, including 24-hour concierge, rooftop terrace with panoramic city views and BBQs, fitness centre, party room with billiards, private theatre, guest suites, pet spa, and bike storage. Located steps to St. Clair West TTC, with Avenue Road, Forest Hill Village, Casa Loma, shops, restaurants, parks, and everyday conveniences all close by, this is Midtown living with comfort, character, and connection. One owned parking space. One owned locker. One very good decision. Walk every room right now through the full Matterport 3D virtual tour in the listing, then book your private showing. Once you experience the layout, the light, and the sense of space, you'll understand why Suite 1106 stands apart. More details
    Listed by RE/MAX REALTRON REALTY INC.
    LISTING DETAILS

  • 402 394 Avenue Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13412480

    402 394 Avenue Road Casa Loma Toronto M4V 2H4
    Main Photo: 402 394 Avenue Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13412480

    402 394 Avenue Road Toronto M4V 2H4 Casa Loma

    $2,495
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C13412480
    Bedrooms:
    2
    Bathrooms:
    1
    *** TWO FREE MONTHS on a 2 year lease or ONE MONTH FREE on a 1 year lease *** PLUS $1,500 credit in 3rd month *** Quick move ins can be accommodated *** Students, Professionals, 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

  • 119 2 Clarendon Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13411824

    119 2 Clarendon Avenue Casa Loma Toronto M4V 1H9
    Main Photo: 119 2 Clarendon Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13411824

    119 2 Clarendon Avenue Toronto M4V 1H9 Casa Loma

    $2,695
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C13411824
    Bedrooms:
    1
    Bathrooms:
    1
    *** TWO FREE MONTHS on a 2 year lease or ONE MONTH FREE on a 1 year lease *** PLUS $1,500 credit in 3rd month *** Rent controlled building *** Welcome to 2 Clarendon Ave - a meticulously restored 1920s heritage residence in prestigious Forest Hill offering refined luxury living. Featuring oak hardwood floors, granite countertops, premium appliances, custom built-ins, and spa-inspired bathrooms with heated floors and towel racks. Residents enjoy an elegant historic lobby, modern gym with steam bath, landscaped grounds, underground parking with EV charging, and private outdoor spaces - a truly high-end living experience where heritage meets contemporary luxury. More details
    Listed by RE/MAX REALTRON REALTY INC.
    LISTING DETAILS

  • 215 396 Avenue Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13277768

    215 396 Avenue Road Casa Loma Toronto M4V 2H5
    Main Photo: 215 396 Avenue Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13277768

    215 396 Avenue Road Toronto M4V 2H5 Casa Loma

    $1,695
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C13277768
    Bathrooms:
    1
    *** TWO FREE MONTHS on a 2 year lease or ONE MONTH FREE on a 1 year lease *** PLUS $750 credit in 3rd month *** Students, Professionals, and Newcomers welcome *** Rent controlled building *** Quick move ins can be accommodated *** 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. More details
    Listed by RE/MAX REALTRON REALTY INC.
    LISTING DETAILS
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Data was last updated June 16, 2026 at 06:15 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 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.