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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  • 181A Poplar Plains Road in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C12845590

    181A Poplar Plains Road Casa Loma Toronto M4V 2N1
    Main Photo: 181A Poplar Plains Road in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C12845590

    181A Poplar Plains Road Toronto M4V 2N1 Casa Loma

    $2,500,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12845590
    Bedrooms:
    5
    Bathrooms:
    6
    A distinguished opportunity to acquire a 33.5 ft x 136.5 ft parcel in the heart of South Hill, moments from the private, gated enclave of Edmund Gate. With its deeper lot configuration, this approved severed property offers enhanced design flexibility and the ability to create a residence with exceptional flow, natural light, and meaningful outdoor integration. The proposed vision supports approximately 3,800 sq ft above grade plus 1,600 sq ft below grade, totaling 5,400 sq ft of elegant living space. The generous depth allows for expansive principal rooms, a thoughtfully proportioned rear garden, and a full-height lower level suited to recreation, wellness, or entertainment. This scale of new construction is increasingly rare within this tightly held and architecturally protected neighbourhood. Surrounded by mature canopy, estate residences, and enduring architectural character, this address offers privacy, prestige, and proximity, just moments to Summerhill, Yorkville, top-tier schools, transit, and the city's ravine network. A strategic acquisition for a builder seeking premium infill with strong end-user appeal. An inspiring foundation for an end user envisioning a refined and enduring custom home in one of Toronto's most distinguished residential pockets. Severance has been approved and all conditions have been waived. The Seller will complete the final severance steps at their own cost as a condition of closing. There will be no severance-related costs to the Buyer. Architectural drawings and consultant reports have been completed and fully paid for. The Buyer will be responsible for City application fees, permit fees, and construction-related costs. The Seller is willing to assist with the permit submission process at the Buyer's expense. More details
    Listed by ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM
    LISTING DETAILS

  • 181 Poplar Plains Road in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C12845484

    181 Poplar Plains Road Casa Loma Toronto M4V 2N1
    Main Photo: 181 Poplar Plains Road in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C12845484

    181 Poplar Plains Road Toronto M4V 2N1 Casa Loma

    $4,500,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12845484
    Bedrooms:
    4
    Bathrooms:
    4
    Presenting a truly rare offering in the heart of South Hill, one of Toronto's most established, architecturally significant, and tightly held enclaves. Moments from the private, gated avenue of Edmund Gate, 181 Poplar Plains Rd represents an extraordinary 67 x 144.64 ft landholding, a scale and presence seldom available in this supply-constrained luxury neighbourhood. Acquired in its entirety, the property offers the opportunity to create a landmark custom residence of approximately 7,600 sq ft above grade (subject to final approvals), allowing a purchaser to fully capitalize on the site's exceptional frontage, depth, and architectural potential. For those seeking flexibility, Committee of Adjustment approval has been secured for severance into two 33.5 ft parcels (181A and 181B Poplar Plains Rd). The proposed configuration supports approximately 3,800 sq ft above grade plus 1,600 sq ft below grade per residence (5,400 sq ft total), delivering meaningful scale for contemporary luxury homes in a neighbourhood where large-format new construction is exceptionally limited. Surrounded by mature canopy, estate residences, and enduring architectural character, this address offers privacy, prestige, and proximity, just moments to Summerhill, Yorkville, top-tier schools, transit, and the city's ravine network. A compelling acquisition for a builder pursuing premium infill. An exceptional canvas for an end user envisioning a generational legacy home in one of Toronto's most distinguished residential pockets. More details
    Listed by ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM
    LISTING DETAILS

  • 307 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12843304

    307 377 Madison Avenue Casa Loma Toronto M4V 3E1
    Main Photo: 307 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12843304

    307 377 Madison Avenue Toronto M4V 3E1 Casa Loma

    $2,750
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C12843304
    Bedrooms:
    2
    Bathrooms:
    2
    Ideally situated on a quiet, tree-lined street just south of Casa Loma! 377 Madison Ave offers a rare blend of neighbourhood charm and urban convenience. This boutique building is nestled between Forest Hill and The Annex, a two-minute walk to Dupont Station, transit, cafés, and everyday essentials. Enjoy this beautifully appointed west-facing suite, featuring nearly 9' ceilings and laminate hardwood flooring throughout. There's an abundance of natural light flooding the suite and two west-facing balconies perfect for taking in the stunning Casa Loma scenery all year round. The kitchen is finished with quartz countertops, floor-to-ceiling cabinetry for ample storage, and premium Fulgar Milano and Blomberg appliances. A custom built-in banquette anchors the dining area. The primary bedroom includes direct access to one of the balconies, while the den provides an ideal work-from-home space. This suite features an exceptionally rare, extra-large walk-in laundry room with stackable Blomberg washer and dryer and ample storage surrounding. Building amenities include 24-hour concierge, a gym, party room, pet spa, and visitor parking! More details
    Listed by KELLER WILLIAMS EMPOWERED REALTY
    LISTING DETAILS

  • 181B Poplar Plains Road in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C12845548

    181B Poplar Plains Road Casa Loma Toronto M4V 2N1
    Main Photo: 181B Poplar Plains Road in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C12845548

    181B Poplar Plains Road Toronto M4V 2N1 Casa Loma

    $2,200,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12845548
    Bedrooms:
    5
    Bathrooms:
    6
    An exceptional opportunity to secure a premier 33.5 ft x 122.6 ft parcel in the heart of South Hill, moments from the private, gated enclave of Edmund Gate. With severance approved and to be finalized as a condition of closing this lot offers the scale and proportions to deliver a striking contemporary residence defined by clean lines, expansive detailing, and meaningful curb presence. The proposed design supports approximately 3,800 sq ft above grade plus 1,600 sq ft below grade, for a total of 5,400 sq ft of refined living space. The lot width allows for a commanding exterior facade and generous interior layout, including spacious principal rooms, full-height lower-level living areas, and integrated garage access. This is a rare opportunity to build new at a meaningful scale in a neighbourhood where large-format construction is exceptionally limited. Surrounded by mature canopy, estate residences, and enduring architectural character, this address offers privacy, prestige, and proximity, just moments to Summerhill, Yorkville, top-tier schools, transit, and the city's ravine network. A compelling acquisition for a builder pursuing premium infill. An exceptional canvas for an end user envisioning a generational legacy home in one of Toronto's most distinguished residential pockets. Severance has been approved and all conditions have been waived. The Seller is completing the final severance steps at their own cost. There will be no severance-related costs to the Buyer. Architectural drawings and consultant reports have been completed and fully paid for. The Buyer will be responsible for City application fees, permit fees, and construction-related costs. The Seller is willing to assist with the permit submission process at the Buyer's expense. More details
    Listed by ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM
    LISTING DETAILS

  • 239 380 Macpherson Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12840516

    239 380 Macpherson Avenue Casa Loma Toronto M4V 3E3
    Main Photo: 239 380 Macpherson Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12840516

    239 380 Macpherson Avenue Toronto M4V 3E3 Casa Loma

    $4,000
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C12840516
    Bedrooms:
    2
    Bathrooms:
    1
    MOVE IN READY! Welcome to The Iconic Madison Lofts! Where contemporary sophistication meets timeless charm in the prestigious Casa Loma enclave. This impeccably fully furnished, open-concept residence showcases soaring 14 foot ceilings, wall-to-wall windows, and an effortless flow that exudes modern elegance. Featuring One Bedroom plus a Den, this suite offers refined comfort and style in every detail. Step onto your private, south-facing balcony and enjoy tranquil city views. The perfect retreat for ANYONE. Residents of The Madison Lofts enjoy a curated selection of amenities, including an expansive rooftop terrace with breathtaking vistas and BBQ lounges ideal for entertaining. Additional amenities include a fitness centre, rejuvenating steam room, inviting party space, 24-hour concierge service, and ample visitor parking. Ideally situated steps from the subway, boutique shops, and fine dining and mere minutes from downtown Toronto. The Madison Lofts offers an elevated urban lifestyle in one of the city's most coveted neighbourhoods. Come see it yourself! More details
    Listed by MIRA INTERNATIONAL REALTY BROKERAGE INC.
    LISTING DETAILS
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    please create a free account

  • 239 380 Macpherson Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12840616

    239 380 Macpherson Avenue Casa Loma Toronto M4V 3E3
    Main Photo: 239 380 Macpherson Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12840616

    239 380 Macpherson Avenue Toronto M4V 3E3 Casa Loma

    $3,200
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C12840616
    Bedrooms:
    2
    Bathrooms:
    1
    MOVE IN READY! Welcome to The Iconic Madison Lofts! Where contemporary sophistication meets timeless charm in the prestigious Casa Loma enclave. Enjoy the open-concept residence showcases soaring 14 foot ceilings, wall-to-wall windows, and an effortless flow that exudes modern elegance. Featuring One Bedroom plus a Den, this suite offers refined comfort and style in every detail. Step onto your private, south-facing balcony and enjoy tranquil city views. The perfect retreat for ANYONE. Residents of The Madison Lofts enjoy a curated selection of amenities, including an expansive rooftop terrace with breathtaking vistas and BBQ lounges ideal for entertaining. Additional amenities include a fitness centre, rejuvenating steam room, inviting party space, 24-hour concierge service, and ample visitor parking. Ideally situated steps from the subway, boutique shops, and fine dining and mere minutes from downtown Toronto. The Madison Lofts offers an elevated urban lifestyle in one of the city's most coveted neighbourhoods. Come see it yourself! More details
    Listed by MIRA INTERNATIONAL REALTY BROKERAGE INC.
    LISTING DETAILS
    To access this listing,
    please create a free account

  • 206 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12838550

    206 377 Madison Avenue Casa Loma Toronto M4V 2W7
    Main Photo: 206 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12838550

    206 377 Madison Avenue Toronto M4V 2W7 Casa Loma

    $3,200
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C12838550
    Bedrooms:
    2
    Bathrooms:
    2
    Welcome to South Hill on Madison. A Sought-after Boutique Condo At The Foot Of Casa Loma.9' Ceiling. Entertainer's kitchen features luxury built-in, panelled appliances and stone countertops. Host in style with a spacious den/dining area that easily accommodates a full dining setup. Thoughtfully designed two-bedroom unit with bright southwest exposure. High-end, modern finishes and fixtures throughout and an ensuite laundry nook. Two Bright bedrooms with a walkout to a balcony. Quiet courtyard exposure. The unit comes with a fully enclosed locker room and a covered parking spot. Enjoy the convenience of condo living: 24-hour concierge, gym, yoga room and more. 3 Mins Steps To Dupont Subway Station, 2 Mins Steps To George Brown Casa Loma Campus, 2 Stops By Subway To U Of T St George Campus. The best of city living! More details
    Listed by RE/MAX EXCEL REALTY LTD.
    LISTING DETAILS

  • 407 2 Clarendon Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12830668

    407 2 Clarendon Avenue Casa Loma Toronto M4V 1H9
    Main Photo: 407 2 Clarendon Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12830668

    407 2 Clarendon Avenue Toronto M4V 1H9 Casa Loma

    $6,095
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C12830668
    Bedrooms:
    2
    Bathrooms:
    2
    *** One month FREE RENT *** Rent controlled building *** Welcome to 2 Clarendon Ave, nestled in the heart of prestigious Forest Hill, where luxury living is redefined in a heritage building from the 1920s, meticulously restored with an unwavering attention to detail. The interior and exterior renovation marries timeless architecture with contemporary finishes, featuring oak hardwood floors, elegant granite countertops, high end appliances, and practical custom built-ins for maximum convenience. For elevated comfort, bathrooms are equipped with heated floors, heated towel racks, and fog-free mirrors. The grand patrimonial lobby, adorned with restored fragments of Casa Loma, leads to an array of newly updated common areas including a state-of-the-art gym equipped with a steam bath, a generously sized lounge, and a welcoming exterior terrace perfect sanctuaries for relaxation and socializing. The property is enveloped in lush landscaped surroundings that enhance its tranquil ambiance. Additional amenities tailored for modern living include a secure bike storage and an underground garage equipped with EV charging stations. Every urban amenity is just a short walk away, including transit, groceries, restaurants, shopping, parks and trails. Experience unparalleled sophisticated living where luxury and history blend seamlessly in one of Toronto's most esteemed locales. Promotion: one month free, applied to 8th month of first year of tenancy. More details
    Listed by RE/MAX REALTRON REALTY INC.
    LISTING DETAILS

  • 502 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C12828446

    502 377 Madison Avenue Casa Loma Toronto M4V 3E1
    Main Photo: 502 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C12828446

    502 377 Madison Avenue Toronto M4V 3E1 Casa Loma

    $630,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C12828446
    Bedrooms:
    2
    Bathrooms:
    1
    Welcome to South Hill on Madison. Sought-after boutique building, perfectly located in desirable Casa Loma. Thoughtfully designed one plus den unit with bright south exposure. Entertainer's kitchen features luxury built-in, paneled appliances and stone countertops. Host in style with a spacious den/dining area that easily accommodates a full dining setup. High-end, modern finishes and fixtures throughout and ensuite laundry nook. Generous living room with walkout to balcony. Quiet courtyard exposure. Unit comes with a fully enclosed locker room and covered parking spot. Enjoy the convenience of condo living: 24 hour concierge, gym, yoga room and more. Coveted Casa Loma location. Steps to subway, popular Dupont Strip cafes, shops and restaurants. The best of city living! More details
    Listed by SUTTON GROUP-ASSOCIATES REALTY INC.
    LISTING DETAILS

  • 316 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12825876

    316 377 Madison Avenue Casa Loma Toronto M4V 3E1
    Main Photo: 316 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12825876

    316 377 Madison Avenue Toronto M4V 3E1 Casa Loma

    $2,250
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C12825876
    Bedrooms:
    1
    Bathrooms:
    1
    Welcome to a one-of-a-kind boutique Art Deco residence nestled at the foot of Casa Loma. This thoughtfully designed, partially furnished 1-bedroom, 1-bathroom suite offers approx. 500 square feet of beautifully functional living space with refined, modern finishes throughout. Soaring 10-foot ceilings and expansive windows fill the suite with natural light, while the efficient layout maximizes every inch. Step out onto your large north-facing private balcony -a quiet retreat above the city.Thoughtful upgrades include custom California Closets built-in drawers within the bedroom closet, as well as a built-in desk and entertainment system - ideal for working from home. Enjoy access to premium amenities including a fully equipped fitness centre, yoga studio, pet spa, and 24-hour concierge and security. For added convenience, the unit comes furnished with a sofa and bed frame - making it effortlessly move-in ready. A great opportunity to live in one of Toronto's most architecturally charming and distinguished addresses. More details
    Listed by SAGE REAL ESTATE LIMITED
    LISTING DETAILS

  • 74B Rathnelly Avenue in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C12810478

    74B Rathnelly Avenue Casa Loma Toronto M4V 2M6
    Main Photo: 74B Rathnelly Avenue in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C12810478

    74B Rathnelly Avenue Toronto M4V 2M6 Casa Loma

    $3,999,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12810478
    Bedrooms:
    3
    Bathrooms:
    5
    Welcome to 74B Rathnelly Ave - a brand-new built 2025, never-lived-in, custom-built luxury home in the prestigious Republic of Rathnelly, one of Toronto's most in-demand neighbourhoods. Steps to Yorkville and close to some of Canada's top private and public schools, this is a truly rare offering with exceptional design, craftsmanship, and high-end finishes throughout.Featuring German-imported Schüco aluminum windows and doors with triple-glazed glass, wide-plank white oak flooring, and a sleek trimless modern design with drywall-groove detailing. Impeccable interior detailing includes custom wall paneling and millwork, a statement mono-beam staircase, glass railings throughout, and upgraded strip lighting/fixtures. Chef's kitchen with custom-painted cabinetry, premium Sub-Zero & Wolf appliances, and natural stone countertops including Super White. Natural stone carries throughout the home (vanities, basement bar, fireplace), highlighted by a dramatic triple-sided marquee fireplace. Spa-inspired bathrooms feature CariMali Italian fixtures and wall-hung Duravit toilets, plus Italian tile and slab finishes with a strong focus on the Italian-slab basement.Enjoy a two-level, double-height heated basement with a large rec room and bar area. The exterior impresses with high-quality linear brick wrapping the sides/rear/walkout, extensive interlock (including interlock driveway), and a standout snow-melt heated system in the driveway, front porch, heated garage area, rear walkout, and even select portions of the backyard for year-round comfort. Entertain on the composite deck and enjoy a large backyard rarely found in the area, complete with composite fencing for a clean, modern finish.Integrated heated garage (extremely rare in the neighbourhood), two furnaces + two A/C systems, high-efficiency spray-foam insulation, smart security/speaker system, central vacuum, and more - a true turnkey statement home in an A+ location. More details
    Listed by RIGHT AT HOME REALTY
    LISTING DETAILS

  • 425 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12804550

    425 377 Madison Avenue Casa Loma Toronto M4V 3E1
    Main Photo: 425 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12804550

    425 377 Madison Avenue Toronto M4V 3E1 Casa Loma

    $1,900
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C12804550
    Bathrooms:
    1
    Welcome to this spacious, carpet-free studio in a boutique low-rise building, ideally located in one of Toronto's most sought-after neighborhoods. Thoughtfully designed and larger than most studios, with high 9' ceilings, this quiet and well-maintained suite features sleek quartz countertops throughout and a generously sized private balcony-perfect for entertaining or relaxing outdoors. Enjoy the convenience of walking to Dupont Subway Station, George Brown College, Casa Loma, Forest Hill, the Annex, and the world-class shops and restaurants of Yorkville. The building offers exceptional amenities, including a fully equipped gym, party room, visitor parking, 24-hour concierge, pet spa. Tenant Pays Hydro and Tenants' Condo Insurance. More details
    Listed by RIGHT AT HOME REALTY
    LISTING DETAILS
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Data was last updated March 5, 2026 at 04:15 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.