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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  • B 314 Avenue Road in Toronto: Casa Loma House for lease (Toronto C02) : MLS®# C14089182

    B 314 Avenue Road Casa Loma Toronto M4V 2H3
    Main Photo: B 314 Avenue Road in Toronto: Casa Loma House for lease (Toronto C02) : MLS®# C14089182

    B 314 Avenue Road Toronto M4V 2H3 Casa Loma

    $3,400
    Residential Freehold
    Status:
    For Lease
    MLS® Num:
    C14089182
    Bedrooms:
    2
    Bathrooms:
    1
    Welcome to this spacious 2-bedroom apartment in the heart of South Hill, one of Toronto's most coveted neighbourhoods. Offering the perfect blend of space, character and convenience, this bright home features soaring ceilings, hardwood floors, a cozy gas fireplace and generous bedrooms, each with ample closet space and a dedicated office nook.Enjoy your own private entrance and a large private deck overlooking beautiful greenspace, perfect for morning coffee, summer BBQs or outdoor dining. A charming flower bed is also available for planting your own herbs or seasonal favourites. The oversized storage closet provides plenty of room for bikes, sports equipment and all the extras that come with city living.An unbeatable location just a 7-minute walk to Rosedale Subway Station, with easy access to Yonge Street, Summerhill, Rosedale and the vibrant shops, cafés and restaurants of Yonge & St. Clair. With transit at the door, quick access to the 401 and Gardiner Expressway, and one parking space included, this is city living with room to breathe. More details
    Listed by ROYAL LEPAGE ESTATE REALTY
    LISTING DETAILS

  • 106 380 Macpherson Avenue in Toronto: Casa Loma Condo Townhouse for sale (Toronto C02) : MLS®# C14085956

    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®# C14085956

    106 380 Macpherson Avenue Toronto M4V 3E3 Casa Loma

    $1,395,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C14085956
    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

  • 21 260 Russell Hill Road in Toronto: Casa Loma Condo Townhouse for sale (Toronto C02) : MLS®# C14034826

    21 260 Russell Hill Road Casa Loma Toronto M4V 2T3
    Main Photo: 21 260 Russell Hill Road in Toronto: Casa Loma Condo Townhouse for sale (Toronto C02) : MLS®# C14034826

    21 260 Russell Hill Road Toronto M4V 2T3 Casa Loma

    $2,999,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C14034826
    Bedrooms:
    5
    Bathrooms:
    6
    Tucked Into South Hill, Steps From Avenue Road And St. Clair, This Is The Rare Townhome That Lives Like A House With None Of The Upkeep. West-Facing And Set At The Centre Of The Enclave, It Enjoys Unobstructed Park Views And Sunsets Every Evening. 3569 Sq Ft Across Four Levels, All Served By A Private Four-Stop Elevator. The Main Floor Is Made For Entertaining: Coffered Ceilings In The Living And Dining Rooms, A Gas Fireplace, French Doors, Custom Beams And Millwork. The Kitchen Pairs Calacatta Marble With Sub-Zero, Miele And Thermador Appliances, A Shaws Of England Farm Sink And A Glass And Stainless Eat-In Bar, Opening To A Sunlit Breakfast Room. Newly Refinished Bleached Oak Floors, Crown Moulding And 7-Inch Baseboards Carry Throughout, While Two Oversized Skylights Pour Light Down Circular Staircases Dressed In Custom Stark Carpet. Four Bedrooms And Six Baths With Granite Counters. The Third-Floor Primary Retreat Offers Two Built-In Walk-In Closets And A Spa Ensuite With Jacuzzi Tub And Bidet. On The Second Level, A Guest Suite With Its Own Ensuite Walks Out To A Private Terrace Under Open Sky And Canopy. The Newly Refinished Lower Level Adds A Rec Room With Custom Built-Ins, Engineered Hardwood, Laundry And Powder Room. Two Underground Parking Spaces With Direct Entry, Plus Fob Access, Security Cameras And Controlled Entry. Out Back, A Walled Garden With Gas BBQ Hook-Up: Private, Still And Entirely Unexpected. For Those Leaving A Large House Who Refuse To Leave Their Life Behind, The Heirlooms, The Crystal And The Art Gathered Over Decades All Find Their Place Here. Lock The Door, Head To The Cottage, And Return To Everything Exactly As You Left It. A Rare Offering In One Of Toronto's Most Quietly Exclusive Enclaves. More details
    Listed by FOREST HILL REAL ESTATE INC.
    LISTING DETAILS

  • 67 Warren Road in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C14083946

    67 Warren Road Casa Loma Toronto M4V 2R9
    Main Photo: 67 Warren Road in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C14083946

    67 Warren Road Toronto M4V 2R9 Casa Loma

    $3,295,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C14083946
    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

  • 11 260 Russell Hill Road in Toronto: Casa Loma Condo Townhouse for sale (Toronto C02) : MLS®# C14031776

    11 260 Russell Hill Road Casa Loma Toronto M4V 2T2
    Main Photo: 11 260 Russell Hill Road in Toronto: Casa Loma Condo Townhouse for sale (Toronto C02) : MLS®# C14031776

    11 260 Russell Hill Road Toronto M4V 2T2 Casa Loma

    $2,799,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C14031776
    Bedrooms:
    4
    Bathrooms:
    5
    Sophisticated And Elegant Townhome In Prestigious South Hill! Offering Approximately 3,500 Sq. Ft. Of Total Living Space, Recently Renovated With Beautifully Updated Landscaping. Sun-Filled Open-Concept Living And Dining Areas Feature 10-Ft Ceilings And Crown Mouldings. Hardwood Flooring Throughout All Four Levels. Spacious Kitchen With Stainless Steel Appliances, Breakfast Area And Family Room With Walkout To Charming Private Patio. Entire Second Floor Dedicated To Luxurious Primary Suite With His-And-Hers Walk-In Closets . Third-Floor Open Library/Home Office. Private Elevator And Direct Lower-Level Access To Two Parking Spaces. Steps To The Village, Minutes To Downtown, BSS, UCC And Excellent Schools. Exceptional Opportunity In One Of Toronto's Most Desirable Neighbourhoods! More details
    Listed by SOTHEBY'S INTERNATIONAL REALTY CANADA
    LISTING DETAILS

  • 528 398 Avenue Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C14029262

    528 398 Avenue Road Casa Loma Toronto M4V 2H4
    Main Photo: 528 398 Avenue Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C14029262

    528 398 Avenue Road Toronto M4V 2H4 Casa Loma

    $2,095
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C14029262
    Bedrooms:
    1
    Bathrooms:
    1
    *** 2 FREE months on a 1 year lease or 3 FREE months on a 19 month lease *** Professionals, Students 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

  • 282 Avenue Road in Toronto: Casa Loma Commercial for sale (Toronto C02) : MLS®# C14028356

    282 Avenue Road Casa Loma Toronto M4V 2G7
    Main Photo: 282 Avenue Road in Toronto: Casa Loma Commercial for sale (Toronto C02) : MLS®# C14028356

    282 Avenue Road Toronto M4V 2G7 Casa Loma

    $1,899,000 /For Sale
    Commercial
    Status:
    Active
    MLS® Num:
    C14028356
    Total Area:
    2,464.93 sq. ft.
    Seller take-back financing is available on attractive terms. Vacant possession of commercially zoned main floor space is possible. A rare opportunity to acquire a full three-storey semi-detached brick building in a highly sought-after Avenue Road location, offering exceptional flexibility and long-term potential for investors, developers, and entrepreneurs. Currently configured as five residential apartments with strong long term tenants and four parking spaces at the rear, the property provides existing residential income while offering the opportunity to capitalize on the mix of permitted residential and commercial uses along this stretch of Avenue Road. Set in an incredibly convenient location, just minutes from Summerhill, Yorkville, Yonge & Bloor and Toronto's downtown core, with excellent TTC access and approximately a 10-minute walk to both Summerhill and Dupont subway stations. Surrounded by established neighborhoods, amenities, restaurants, shops and transit, the location offers strong appeal for both residential and commercial users. Being sold as-is, where-is, this is an outstanding opportunity to acquire a versatile Avenue Road property and unlock its full potential in one of Toronto's most desirable and well-connected areas. More details
    Listed by RE/MAX HALLMARK REALTY LTD.
    LISTING DETAILS

  • 106 2 Clarendon Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C14029264

    106 2 Clarendon Avenue Casa Loma Toronto M4V 1H9
    Main Photo: 106 2 Clarendon Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C14029264

    106 2 Clarendon Avenue Toronto M4V 1H9 Casa Loma

    $3,295
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C14029264
    Bedrooms:
    1
    Bathrooms:
    1
    *** 2 FREE months on a 12 month lease or 3 FREE months on a 19 month lease *** 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, 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

  • 120 2 Clarendon Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C14029430

    120 2 Clarendon Avenue Casa Loma Toronto M4V 1H9
    Main Photo: 120 2 Clarendon Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C14029430

    120 2 Clarendon Avenue Toronto M4V 1H9 Casa Loma

    $2,595
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C14029430
    Bedrooms:
    1
    Bathrooms:
    1
    *** 2 FREE months on a 12 month lease or 3 FREE months on a 19 month lease *** 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, 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

  • Commercial in Toronto

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    Main Photo: Commercial in Toronto

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    Commercial
    LISTING DETAILS
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  • 74B Rathnelly Avenue in Toronto: Casa Loma House for lease (Toronto C02) : MLS®# C13886492

    74B Rathnelly Avenue Casa Loma Toronto M4V 2M6
    Main Photo: 74B Rathnelly Avenue in Toronto: Casa Loma House for lease (Toronto C02) : MLS®# C13886492

    74B Rathnelly Avenue Toronto M4V 2M6 Casa Loma

    $17,000
    Residential Freehold
    Status:
    For Lease
    MLS® Num:
    C13886492
    Bedrooms:
    3
    Bathrooms:
    5
    Welcome to 74B Rathnelly Ave, a brand-new, custom-built luxury home (2025) in the prestigious Republic of Rathnelly, one of Toronto's most sought-after neighbourhoods. Located steps to Yorkville and close to some of Canada's top private and public schools, this is a rare lease opportunity in an exceptional location.This stunning home features German-imported Schuco aluminum windows and doors with triple-glazed glass, wide-plank white oak flooring, and a sleek trimless modern design with custom wall paneling, millwork, a striking mono-beam staircase, glass railings, and upgraded lighting throughout.The chef's kitchen is equipped with custom cabinetry, Sub-Zero & Wolf appliances, and natural stone countertops, including Super White stone. Natural stone continues throughout the home in the vanities, basement bar, and fireplace, while the spa-inspired bathrooms offer CariMali Italian fixtures, Duravit wall-hung toilets, and elegant Italian tile and slab finishes.The two-level, double-height heated basement includes a large rec room and bar area, perfect for entertaining. Outside, enjoy linear brick exterior detailing, extensive interlock, a composite deck, large backyard, and composite fencing. A standout feature is the snow-melt heated system in the driveway, front porch, heated garage area, rear walkout, and parts of the backyard.Additional features include an integrated heated garage, two furnaces, two A/C systems, spray-foam insulation, smart security/speaker system, central vacuum, and more.A truly turnkey luxury lease in an A+ location. More details
    Listed by RIGHT AT HOME REALTY
    LISTING DETAILS

  • 25 Clarendon Avenue in Toronto: Casa Loma House for lease (Toronto C02) : MLS®# C13879230

    25 Clarendon Avenue Casa Loma Toronto M4V 1H8
    Main Photo: 25 Clarendon Avenue in Toronto: Casa Loma House for lease (Toronto C02) : MLS®# C13879230

    25 Clarendon Avenue Toronto M4V 1H8 Casa Loma

    $6,950
    Residential Freehold
    Status:
    For Lease
    MLS® Num:
    C13879230
    Bedrooms:
    4
    Bathrooms:
    4
    A unique offering in coveted South Hill, 25 Clarendon Ave is a turnkey Detached Home ideal for busy Families, Office space and/or Entertaining. It offers a rare combination of features, including a coveted Private Double Driveway that easily fits 4 cars, as well as a separate single Garage. Comprised of Three Above Grade Levels, the practical layout of this home includes both formal & more relaxed living spaces. The Expansive Bright Kitchen with Centre Island has upgraded Appliances, a wall of Windows & plenty of room for the Family Breakfast Table. The Oversized Living Room features a striking Marble Fireplace, South facing windows & leads into a Beautiful Dining Room with Sliding Doors opening to a Sunny Modern Balcony. This provides accessible Outdoor Space from the Main Floor & fits a table & chairs as well as a BBQ. Three good sized Bedrooms & two Baths are found on the Upper Level. The Principal Bedroom has an Ensuite with Double Sinks & an Oversized Glass Shower. The additional Family Bathroom has another Glass Shower as well as an Oversized Whirlpool Tub. The Lower Level features a Mudroom with extensive Built-In Shelving & Double Doors leading out to a gorgeous new Backyard Courtyard. It is incredibly Private with a Professionally Landscaped City Garden. The Family or TV Room also on this Level was built with extra soundproofing & is near a Private Entrance - a Perfect Option for a Home Business or Office to Welcome Clients. This Flexible Lease is available for a minimum of 6 Months & can be Furnished with the existing French Antiques, Unfurnished or even Partially Furnished at Tenant's request. Centrally located & Walking Distance to Subways, excellent Private & Public Schools, Parks, Shops, Cafes/Restaurants, & Groceries. This home is only 1 block from the Ave Rd Bus, providing easy access to Yorkville & commuting to the Financial District & Hospitals. Don't miss this Warm, Cheerful & Sophisticated Home, amenable to a variety of Tenant Lifestyles. More details
    Listed by CHESTNUT PARK REAL ESTATE LIMITED
    LISTING DETAILS
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Data was last updated October 18, 2026 at 01:15 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.