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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  • 67 Warren Road in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C13786652

    67 Warren Road Casa Loma Toronto M4V 2R9
    Main Photo: 67 Warren Road in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C13786652

    67 Warren Road Toronto M4V 2R9 Casa Loma

    $3,695,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C13786652
    Bedrooms:
    4
    Bathrooms:
    5
    Welcome to 67 Warren Road, a rare South Hill find offering 3,000 sqft of living space in an incredible location. This spacious family home offers 4+2 bedrooms, 5 bathrooms and the opportunity to move in and enjoy today, update now, or make it your own over time.The main floor is designed for both everyday family living and entertaining, with open-concept living and dining spaces, a sun-filled sunken family room, gas fireplace and custom built-ins. Outside, the beautifully landscaped backyard is a true highlight, featuring an inground pool, deck with electric awning and plenty of room to relax and entertain.The second and third floors offer four generously sized bedrooms with excellent storage, including a spacious primary suite with ensuite. An additional family room provides flexible space for a home office, lounge or kids' area, while balconies on both upper levels add even more outdoor space.The finished lower level offers two additional bedrooms and an abundance of flexible living space with a separate entrance, ideal for a rec room, gym, nanny or in-law suite, or the potential for a separate home office.Located in the heart of South Hill, just steps to transit, excellent schools and neighbourhood amenities, with Forest Hill, Casa Loma and downtown Toronto all within easy reach. An incredible combination of space, location and potential, and a rare opportunity to make a wonderful South Hill home your own. More details
    Listed by HARVEY KALLES REAL ESTATE LTD.
    LISTING DETAILS

  • PH1 2 Lynwood Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C13784748

    PH1 2 Lynwood Avenue Casa Loma Toronto M4V 1K2
    Main Photo: PH1 2 Lynwood Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C13784748

    PH1 2 Lynwood Avenue Toronto M4V 1K2 Casa Loma

    $5,100,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C13784748
    Bedrooms:
    3
    Bathrooms:
    3
    There are very few penthouses in the city that offer this level of scale and architectural presence while still feeling like a private residence. This is one of them. Spanning nearly 5,000 square feet across two levels, this one of a kind residence crowns an intimate 16 suite boutique building in the heart of South Hill, conceived around this exceptional penthouse. With a layout more akin to a detached home, it offers a level of privacy rarely found in Toronto. A sculptural white staircase in Venetian plaster anchors the refined, modern interior, while matte herringbone floors add warmth throughout. The scale is striking, with a great room featuring 25 foot ceilings and an open flame fireplace, ideal for both entertaining and everyday living. Expansive windows fill the space with natural light, and the dining area and chef's kitchen connect seamlessly. A family room and main floor primary suite offer comfort and privacy. Upstairs, a library with fireplace and wet bar creates a destination space, alongside an additional bedroom suite and a separate office that could convert to a third bedroom. Renderings have also been prepared to illustrate the potential to convert a portion of the interior space into a private New York style terrace, offering a compelling vision of how outdoor living could be seamlessly integrated into the home, an increasingly rare luxury in this setting. With four car parking, concierge, and amenities including a pool and sauna, every detail is considered. Set near Yorkville, St. Clair West, and Forest Hill, the location offers exceptional convenience. But what truly sets this residence apart is its rarity, a unique opportunity to acquire nearly 5,000 square feet in a boutique setting, at a price per square foot that is difficult to replicate in today's market. Opportunities of this calibre are few and far between. More details
    Listed by ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM
    LISTING DETAILS

  • 278 Avenue Road in Toronto: Casa Loma Commercial for sale (Toronto C02) : MLS®# C13778938

    278 Avenue Road Casa Loma Toronto M4V 2G7
    Main Photo: 278 Avenue Road in Toronto: Casa Loma Commercial for sale (Toronto C02) : MLS®# C13778938

    278 Avenue Road Toronto M4V 2G7 Casa Loma

    $1,749,000 /For Sale
    Commercial
    Status:
    Active
    MLS® Num:
    C13778938
    Major Bus.:
    Other
    Total Area:
    2,736 sq. ft.
    Attention Developers, Investors & Entrepreneurs! Welcome to the prestigious Republic of Rathnelly neighbourhood, one of Toronto's most sought-after locations. A rare opportunity to own a prime mixed-use property offering endless possibilities for a customized live/work space, professional office, income-generating rental units, or future redevelopment. Zoning along this stretch of Avenue road permits a mix of residential and commercial uses, making this an exceptional investment in a highly desirable area. This full three-storey brick semi-detached building is ready for your vision. Whether you're looking to create a unique residence offering a business below, design modern office space, or renovate into residential rental units, the potential is outstanding. The property also features a newer detached four-car garage accessed via the rear laneway, which provides valuable private parking or additional flexibility. A short walk to Summerhill, Yorkville, and Yonge & Bloor, with convenient TTC access and only a 10-minute walk to Summerhill or Dupont subway stations. Minutes to Toronto's downtown core. Sold as is, where is, this property presents an incredible opportunity to renovate, reimagine, and make it your own. Listing is also on residential MLS More details
    Listed by SOTHEBY'S INTERNATIONAL REALTY CANADA
    LISTING DETAILS

  • 501 380 Macpherson Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C13778988

    501 380 Macpherson Avenue Casa Loma Toronto M4V 3E3
    Main Photo: 501 380 Macpherson Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C13778988

    501 380 Macpherson Avenue Toronto M4V 3E3 Casa Loma

    $799,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C13778988
    Bedrooms:
    2
    Bathrooms:
    1
    Some condos give you a balcony. This one gives you 155 square feet of private outdoor living, south-facing over the city with an unobstructed view of the CN Tower. Set within Madison Avenue Lofts in Casa Loma, this residence combines distinctive loft character with something increasingly hard to find in Toronto: meaningful outdoor space. Inside, 10-foot ceilings and oversized windows bring in an abundance of natural light, while exposed concrete, ductwork and industrial details give the space its unmistakable loft character. A well-planned layout features a generous kitchen and comfortable living space, opening onto a terrace that feels like a true extension of the home-with room to dine, entertain, garden or simply take in the skyline. Tucked along Macpherson Avenue, a calm residential street that feels removed from the downtown rush, yet keeps some of Toronto's best neighbourhoods within easy reach. Walk to Casa Loma, The Annex, Yorkville, shops, restaurants, parks and the subway. one parking space and locker included. Loft character, natural light, exceptional outdoor space and one of Toronto's most recognizable views-condo living with room to breathe. Thoughtful updates throughout include fresh paint, updated light fixtures and closet built-ins, adding both style and function to the space. More details
    Listed by REMAX YOUR COMMUNITY REALTY
    LISTING DETAILS

  • 521 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13769216

    521 377 Madison Avenue Casa Loma Toronto M4V 2W7
    Main Photo: 521 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13769216

    521 377 Madison Avenue Toronto M4V 2W7 Casa Loma

    $2,200
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C13769216
    Bedrooms:
    1
    Bathrooms:
    1
    Welcome To South Hill On Madison! Located in one of the most iconic areas in Toronto - at the foot of Casa Loma. This spacious loft-style layout offers a spacious living space with an open concept bedroom perfect for both entertaining and relaxing. The modern kitchen is equipped with all built-in sleek appliances and also fitted with an updated bathroom with a sleek glass shower. Location is second to none as you are in a prestigious neighbourhood with endless amenities within a walking distance. This is a place you would love to call home! More details
    Listed by PSR
    LISTING DETAILS

  • Condo Apartment in Toronto

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    Main Photo: Condo Apartment in Toronto

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    Residential Condo & Other
    LISTING DETAILS
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  • 1801 155 St Clair Avenue W in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13766828

    1801 155 St Clair Avenue W Casa Loma Toronto M4V 0A1
    Main Photo: 1801 155 St Clair Avenue W in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13766828

    1801 155 St Clair Avenue W Toronto M4V 0A1 Casa Loma

    $15,500
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C13766828
    Bedrooms:
    3
    Bathrooms:
    3
    Prestigious boutique living at The Avenue, one of Toronto's most sought-after luxury residences, ideally located at Avenue Rd. & St. Clair Ave. W. in the heart of Forest Hill. This elegant 3-bedroom suite offers private elevator access, a separate service entrance with dedicated elevator, and exceptional finishes throughout, including soaring ceilings, hardwood floors, crown mouldings, coffered ceilings, pot lights, custom built-ins, gas fireplace, and motorized window coverings. The gourmet kitchen features premium built-in appliances, gas cooktop, built-in espresso machine, wet bar, large centre island with breakfast bar, and spacious breakfast area. The formal dining room opens to a large south-facing terrace with panoramic city skyline and CN Tower views. The living room includes custom built-in bookcases, while the luxurious primary suite offers a sitting area with terrace access, oversized walk-in closet, and spa-inspired 6-piece ensuite with Jacuzzi tub. Iwo additional bedrooms provide excellent space for family or guests. Includes 2 parking spaces and 1 locker. Building offers resident EV charging. Offered fully furnished for turnkey living or available unfurnished. Residents enjoy exceptional white-glove concierge service, valet parking, indoor pool, fitness centre, party/meeting rooms, guest suites, and ample visitor parking. Steps to parks, walking and cycling trails, top-rated schools, transit, and minutes to Yorkville, Yonge St., fine dining, cafes, luxury shopping, and entertainment. A rare opportunity to lease an exceptional residence in one of Toronto's finest boutique condominium buildings. More details
    Listed by SUTTON GROUP-ADMIRAL REALTY INC.
    LISTING DETAILS

  • 738 Huron Street in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C13758844

    738 Huron Street Casa Loma Toronto M4V 2W3
    Main Photo: 738 Huron Street in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C13758844

    738 Huron Street Toronto M4V 2W3 Casa Loma

    $1,695,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C13758844
    Bedrooms:
    4
    Bathrooms:
    3
    Tucked into one of Toronto's most distinctive neighbourhoods at the foot of Casa Loma, 738 Huron feels instantly welcoming. Behind its classic brick façade, this wide semi offers generous principal rooms, beautiful original details and a layout that unfolds far beyond what you might expect from the street with approximately 1,800 sq. ft. above grade. Restored leaded glass, hardwood floors, crown mouldings and a decorative fireplace give the living and dining rooms warmth and personality, while the rear of the house opens into the space that truly sets this home apart. The sun-filled family room addition is the heart of the house, featuring exposed brick, a gas fireplace, a powder room and striking wrought-iron French doors opening directly onto the garden. It is relaxed, inviting and connected to the outdoors. The adjoining eat-in kitchen offers excellent storage, stone counters, stainless steel appliances Upstairs are two generous bedrooms and a spacious family bathroom with both a soaker tub and glass shower. Above, the finished third-floor loft provides an entirely different kind of space: bright, private and flexible, with a skylight, large window, storage and charming views toward Casa Loma. Use it as a bedroom, office, studio, or playroom. The lower level adds even more versatility, with a separate side entrance, three-piece bath, storage and additional living space well suited to a live-in nanny, guests, teens, work-from-home needs or extended family. Then there is the garden. Mature, beautifully established and exceptionally private, with flagstone and layered greenery, it feels like a tranquil retreat from the city around it. Legal front pad parking completes the package. All of this in an exceptionally central location, steps to Dupont Subway Station, walking distance to the shops, restaurants, and amenities in Yorkville, the Annex and Yonge & St Clair. Top rated public and private schools including Brown & Deer Park, Mabin, Waldorf, York, ICS and more. More details
    Listed by ROYAL LEPAGE REAL ESTATE SERVICES LTD.
    LISTING DETAILS

  • House in Toronto

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    Main Photo: House in Toronto

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    Residential Freehold
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  • 106 380 Macpherson Avenue in Toronto: Casa Loma Condo Townhouse for sale (Toronto C02) : MLS®# C13753068

    106 380 Macpherson Avenue Casa Loma Toronto M4V 3E3
    Main Photo: 106 380 Macpherson Avenue in Toronto: Casa Loma Condo Townhouse for sale (Toronto C02) : MLS®# C13753068

    106 380 Macpherson Avenue Toronto M4V 3E3 Casa Loma

    $1,495,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C13753068
    Bedrooms:
    3
    Bathrooms:
    3
    This is one of the few 3-Bedroom Corner Townhomes at the coveted Madison Ave Lofts with 22-ft Ceilings and a serene Terrace Facing the Quiet, Tree-Lined Courtyard. A Private Entrance, steps from your Door, lets you skip the Lobby all together should you wish. This Bold Art deco inspired Loft is designed for Modern Families, Young Professionals, or Downsizers seeking something Beyond the Ordinary. Step inside and prepare to be stopped in your tracks. A striking Living Room with Dramatic Floor-To-Ceiling Windows Floods this Corner residence with Natural Light. Framed by picturesque views of the Tree-lined Courtyard, the Extraordinary Volume and Openness create a Space that's Sophisticated, Dramatic and Memorable. Wide-Plank Hardwood Floors and a Seamless Glass Staircase set a tone that's Cool, Chic, and Elegant - total Tribeca loft energy in Midtown Toronto.The Chef's Kitchen features Nero Marquina Porcelain Countertops, a Stainless Steel Fridge, Panelled Bosch DW, Custom Breakfast Bar, and a W/I Pantry. The Dining Room, with its High Ceilings, features a Bespoke Backlit Bar, perfect for hosting in Style. Retreat to the Primary Bedroom, complete with a Custom Wall-to-Wall Built-In Unit for added Storage, a Spa-Inspired 5-piece Ensuite, a Walk-In Closet - every closet features custom organizers. The Second Bedroom is a flexible space ready to grow with your needs - Home Office Nursery, or Lounge - currently outfitted as a Gym. Steps to Dupont Station and home to arguably the city's best lox & bagels, coffee shops, and boutique shopping. Stroll to the Annex, Yorkville, Casa Loma, Parks and Ravines. Underground pkg, a storage locker and ***unlimited Bell Fibe Internet & Cable TV, Heat, Water*** includedin Monthly Maintenance Fees. Bldg Amenities: friendly Concierge, Visitor's Parking, an idyllic Rooftop Terrace with BBQs, Gym, Steam Sauna, Theatre, and Party Room. Corner Lofts like this don't come around twice. Your Unit 106 awaits. More details
    Listed by HARVEY KALLES REAL ESTATE LTD.
    LISTING DETAILS

  • 408 380 Macpherson Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C13753284

    408 380 Macpherson Avenue Casa Loma Toronto M4V 3E3
    Main Photo: 408 380 Macpherson Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C13753284

    408 380 Macpherson Avenue Toronto M4V 3E3 Casa Loma

    $1,129,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C13753284
    Bedrooms:
    2
    Bathrooms:
    2
    With so many condos on the market, it takes something special to stand out - and this one does. Welcome to Madison Lofts, where this seriously cool 2-bedroom, 2-bathroom suite offers a smart split-bedroom plan, a bright open-concept layout and the kind of space that actually works for real life. The vibe is modern, urban and anything but cookie-cutter, with plenty of room to live, work and entertain. And then there's the terrace - a fabulous outdoor extension of the living space with an open city outlook and Casa Loma rising above the neighbourhood in the distance. Morning coffee, drinks with friends, dinner outside - this is outdoor space you'll actually use. In a sea of average condos, this one has personality, presence and a view you won't find everywhere. More details
    Listed by FOREST HILL REAL ESTATE INC.
    LISTING DETAILS

  • 408 380 Macpherson Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13752722

    408 380 Macpherson Avenue Casa Loma Toronto M4V 3E3
    Main Photo: 408 380 Macpherson Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13752722

    408 380 Macpherson Avenue Toronto M4V 3E3 Casa Loma

    $4,000
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C13752722
    Bedrooms:
    2
    Bathrooms:
    2
    With so many condos on the market, it takes something special to stand out - and this one does. Welcome to Madison Lofts, where this seriously cool 2-bedroom, 2-bathroom suite offers a smart split-bedroom plan, a bright open-concept layout and the kind of space that actually works for real life. The vibe is modern, urban and anything but cookie-cutter, with plenty of room to live, work and entertain. And then there's the terrace - a fabulous outdoor extension of the living space with an open city outlook and Casa Loma rising above the neighbourhood in the distance. Morning coffee, drinks with friends, dinner outside - this is outdoor space you'll actually use. In a sea of average condos, this one has personality, presence and a view you won't find everywhere More details
    Listed by FOREST HILL REAL ESTATE INC.
    LISTING DETAILS
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Data was last updated September 16, 2026 at 07:15 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.