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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  • 123 1 Benvenuto Place in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C12053118

    123 1 Benvenuto Place Casa Loma Toronto M4V 2L1
    Main Photo: 123 1 Benvenuto Place in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12053118
    $1,895,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C12053118
    Bedrooms:
    3
    Bathrooms:
    3
    Experience refined living at The Benvenuto. This light-filled 1,550 square foot 2 bedroom plus den, 2.5 bathroom suite showcases top-tier finishes highlighted with rich, warm walnut flooring that flows seamlessly throughout. The layout encompasses a spacious living, dining, and kitchen area, perfect for both entertaining and everyday living. The gourmet kitchen, designed by Bellini, features a substantial centre island and superb appliances. The suite is complemented by 2.5 luxuriously appointed bathrooms. "Patton Design" selected upscale, transitional interior finishes to create a sophisticated backdrop for your personal style. Suite 123, a main-level suite, is positioned advantageously on the slope of the hill, offering an elevated perspective, providing views of the historic gothic mansion at De La Salle College with mature trees in the distance. This full-service building offers valet parking, a full-time concierge plus a day porter, on-site management and superintendent personnel, a glass gym on the rooftop, two parking spaces and a locker. Located in the exclusive residential pocket near Avenue Road and St Clair, this mid-century modern masterpiece of a building is exceptionally well maintained and heritage designated. Your tastebuds will be tempted at Scaramouche, on the ground floor. One of Toronto's most illustrious restaurants. You'll adore living at The Benvenuto. More details
    Listed by SOTHEBY`S INTERNATIONAL REALTY CANADA
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  • 1109* 223 St. Clair Avenue W in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C12054221

    1109* 223 St. Clair Avenue W Casa Loma Toronto M4V 0A5
    Main Photo: 1109* 223 St. Clair Avenue W in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12054221
    $1,649,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C12054221
    Bedrooms:
    2
    Bathrooms:
    3
    Welcome to a truly rare offering in Forest Hills coveted Zigg Condos a luxury boutique building completed in 2018. This custom-designed, 1,557 sq ft south-facing suite is the result of two units seamlessly combined, offering a one-of-a-kind layout with jaw-dropping views. From sunrise to sunset, enjoy a constantly changing cityscape with unobstructed sightlines over the downtown skyline, Lake Ontario, and beyond. Bathed in natural light from floor-to-ceiling windows in every room, the condo features wide-plank hardwood flooring, pot lights, and integrated speakers. The chefs kitchen is a standout with two fridges, two stoves, quartz countertops, an integrated breakfast table, and high-end built-ins. The oversized primary suite is a sanctuary, complete with a custom sound-insulated wall, and a spa-like 4-piece ensuite with a rain shower, double vanity, and wide-format tile floors. An infrared sauna and a sizable walk-in laundry in the unit is a luxurious bonus. Top-tier amenities: 24-hr concierge, gym, party room with billiards and theatre, pet spa, guest suites, and an extraordinary rooftop terrace with panoramic city views, BBQs, and designer furnishings. Ideally located steps from the Nordheimer Ravine, St. Clair West, Forest Hill Village, and Yonge & St. Clair, with transit at your doorstep. More details
    Listed by SUTTON GROUP-ASSOCIATES REALTY INC.
  • 1105 223 St Clair Avenue W in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C12053884

    1105 223 St Clair Avenue W Casa Loma Toronto M4V 0A5
    Main Photo: 1105 223 St Clair Avenue W in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12053884
    $849,800
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C12053884
    Bedrooms:
    3
    Bathrooms:
    2
    Welcome to Zigg's Condo, a boutique condo in the exclusive Casa Loma, Forest Hills neighbourhood. This 2 Bedroom + Den & 2 Full Bathroom Unit offers one best layouts in the Building. Unit has Laminate Flooring throughout, 9 Ft Ceilings, Spacious open-concept Living Area, Floor to Ceiling Windows , and a Clear North facing exposure. Den in the Unit offers plenty of space for those who work at home. Kitchen area is appointed with Quartz Counters & complimenting Backsplash and fitted with high end appliances (Wolf Induction Cooktop & Fulgor Milano Oven). Primary Bedroom features an Ensuite Bathroom & Closet with Organizers. Building Amenities include a Beautiful Panoramic Rooftop Terrace with Lounges and Indoor Kitchen, Party/Entertainment Room, Fitness/Gym Room, and Pet Wash Area. Location offer's easy access to TTC Streetcar & Subway Station , Parks , Shopping , Restaurants , and more! 1 Parking and Locker included More details
    Listed by HOME STANDARDS BRICKSTONE REALTY
  • 257&261 Poplar Plains Road in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C12054399

    257&261 Poplar Plains Road Casa Loma Toronto M4V 2N9
    Main Photo: 257&261 Poplar Plains Road in Toronto: Casa Loma House for sale (Toronto C02)  : MLS®# C12054399
    $5,980,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12054399
    Bedrooms:
    11
    Bathrooms:
    7
    Discover an exceptional property in the heart of South Hill, within walking distance to Yonge & St. Clair, top-tier shopping, and highly regarded schools. This offering includes 257 & 261 Poplar Plains Rd., two side-by-side detached homes on a generous 11,880 sq. ft. lot (90' frontage on Poplar Plains Rd. and 132' on Lynwood Ave.).This unique property provides a range of options for buyers looking to enhance its existing charm. Whether you choose to renovate the two spacious homes (each approx. 3,000 sq. ft.), expand, reconfigure, or explore a simple severance into 2-3 lots, the possibilities are endless. Garden suites or new custom-built homes are also an option, allowing you to maximize the space without extensive approvals. Perfect for multi-generational living, investors, or those seeking to create their ideal home in a prime location, this is a rare opportunity in one of Toronto's most desirable neighborhoods. Don't miss out on the potential to create something special in this prestigious community. More details
    Listed by ROYAL LEPAGE REAL ESTATE SERVICES LTD.
  • 46 CLARENDON Avenue in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C12051337

    46 CLARENDON Avenue Casa Loma Toronto M4V 1J1
    Main Photo: 46 CLARENDON Avenue in Toronto: Casa Loma House for sale (Toronto C02)  : MLS®# C12051337
    $2,185,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12051337
    Bedrooms:
    4
    Bathrooms:
    4
    Situated in one of Torontos most sought-after neighbourhoods, this sun-drenched semi-detached gem offers a rare opportunity to own in the heart of South Hill, surrounded by exquisite multi-million-dollar estates. With timeless elegance and classic charm, this home has been meticulously cared for by a single owner for over 30 years, offering a warm and inviting atmosphere. Set on an expansive 150-foot-deep lot, the lush backyard oasis is a private retreat perfect for family gatherings and outdoor entertaining. The inviting covered front porch is the perfect spot to enjoy quiet mornings with coffee, basking in sunlight throughout the day. Inside, the elegant living spaces are anchored by cozy wood-burning fireplaces, encased in granite, creating the perfect ambiance for intimate evenings and lasting memories. The spacious and well-thought-out floor plan creates a perfect flow throughout the home, maximizing space and functionality. The fully finished lower level with a separate entrance provides endless possibilities whether as a private suite for extended family, a nanny, or a ready-to-rent space for additional income. Unparalleled in location, this home is just minutes from Yorkville, Summerhill, and Forest Hill Village, placing the city's finest dining, boutique shopping, and top-tier amenities at your doorstep. Stroll through nearby ravine trails, hop on the subway within moments, and enjoy proximity to some of Torontos best schools. A dream for families and professionals alike. Opportunities like this are few and far between. Experience the timeless elegance and prime location of this South Hill treasure. Book your private viewing today! More details
    Listed by HARVEY KALLES REAL ESTATE LTD.
  • 510 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12051687

    510 377 Madison Avenue Casa Loma Toronto M4V 3E1
    $3,250
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C12051687
    Bedrooms:
    2
    Bathrooms:
    2
    Welcome To South Hill On Madison - A Contemporary Art Deco Condominium Located At The Foot Of Cas Loma, Where Forest Hill Meets The Annex. Luxury Living at South Hill Condos At Casa Loma. Meticulously Maintained, Newly Boutique Condo W/Just 7 Storeys. Spacious Unit W/Well-Proportioned Sizeable Rooms. 9' Smooth Ceilings, Modern Kitchen, Integrated Appliances & Updated Baths. Primary Bed W/Full Ensuite. Huge Closets. 24/7 Concierge, Gym, Visitor Parking, Bike Racks. Walk To Dupont Ttc, Food, Green Space. An Impeccable Place To Call Home, Everything You Need Is Within Walking Distance Making This A True Urban Haven! More details
    Listed by RE/MAX CROSSROADS REALTY INC.
  • 10 260 Russell Hill Road in Toronto: Casa Loma Condo Townhouse for sale (Toronto C02) : MLS®# C12050903

    10 260 Russell Hill Road Casa Loma Toronto M4V 2T2
    Main Photo: 10 260 Russell Hill Road in Toronto: Casa Loma Condo Townhouse for sale (Toronto C02)  : MLS®# C12050903
    $3,295,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C12050903
    Bedrooms:
    4
    Bathrooms:
    5
    This elegant stone townhouse, ideally located in South Hill next to Sir Winston Churchill Park and reminiscent of classic London architecture, has been impressively renovated by designer Kate Zeidler. The open-concept main floor is anchored by a chefs high-end kitchen, making it perfect for entertaining. A lovely living room, dining area, and a spacious family room with built-ins, bar, and fireplace, opens to a charming private stone courtyard. The second floor features a luxurious principal bedroom with a dream ensuite, a walk-in closet and a private balcony. A lovely library/bedroom on this level boasts beautiful built-ins. The third floor offers two large sunlit bedrooms, each with an ensuite, while a skylight above bathes the entire home in natural light. The lower level includes a gym/family room, bringing the total space to approximately 3,400 square feet.This exquisite home features a private elevator accessing all four floors and includes two underground parking spots with direct entry. Steps from transit, within walking distance of Forest Hill Village and Yonge & St. Clair, and near top private schools, 260 Russell Hill Road TH10 is a rare find in exceptional condition. More details
    Listed by CHESTNUT PARK REAL ESTATE LIMITED
  • Th103 223 St Clair Avenue W in Toronto: Casa Loma Condo Townhouse for lease (Toronto C02) : MLS®# C12050593

    Th103 223 St Clair Avenue W Casa Loma Toronto M4V 1R3
    Main Photo: Th103 223 St Clair Avenue W in Toronto: Casa Loma Condo Townhouse for lease (Toronto C02)  : MLS®# C12050593
    $6,000
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C12050593
    Bedrooms:
    4
    Bathrooms:
    3
    Spectacular South Hill Townhome W/Direct Access From St.Clair (Or Access Via Lobby) Approx 1800 Sq Ft Of Sun Filled Space On 2 Floors. Main Floor Powder Room. Upgraded Chef's Kit & Engineered Hardwood Floors. Stone countertops and Stainless Steel Appliances. Open Concept Design. Sun filled Great Space W/ High Ceilings and Oversized Floor To Ceiling Windows. Primary Bedroom W/4 Pc Ensuite & W/I Closet. Ample Storage, Double Closets In 2nd and 3rd Bedroom. Balcony. 1 Underground Parking Spot & Large Locker. Fabulous Amenities, 24 Hr Concierge, Gym, Meeting Rm, And Fabulous Outdoor Roof Top Patio. Excellent Walk Score. Steps To Public Transit, Boutique Markets, Restaurants & Shops. More details
    Listed by RE/MAX REALTRON BARRY COHEN HOMES INC.
  • Lower 296 Avenue Road in Toronto: Casa Loma House for lease (Toronto C02) : MLS®# C12048851

    Lower 296 Avenue Road Casa Loma Toronto M4V 2H1
    Main Photo: Lower 296 Avenue Road in Toronto: Casa Loma House for lease (Toronto C02)  : MLS®# C12048851
    $1,850
    Residential Freehold
    Status:
    For Lease
    MLS® Num:
    C12048851
    Bedrooms:
    1
    Bathrooms:
    1
    Casa Loma Living for modest budget! This newly renovated one bedroom is all you need. Modern living for busy young professionals in an open concept living/dinning/kitchen condo style, all new appliances, closet and window in bedroom. Conveniently located with public transit, min to shops, groceries, 10 minute walk to Davenport Rd to it's vibrant restaurants and other amenities. This unit comes with ensuite laundry and utilities all included with your own private entrance and access to the yard. Parking available for $125extra/month. Make this unit your home! More details
    Listed by ROYAL LEPAGE SIGNATURE REALTY
  • 233 MacPherson Avenue in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C12047575

    233 MacPherson Avenue Casa Loma Toronto M4V 1A1
    Main Photo: 233 MacPherson Avenue in Toronto: Casa Loma House for sale (Toronto C02)  : MLS®# C12047575
    $3,490,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12047575
    Bedrooms:
    4
    Bathrooms:
    5
    Step into this luxurious, renovated residence in the Republic of Rathnelly, a coveted residential enclave on the border of Yorkville and Summerhill. This home is uncompromising, offering family-functional interiors, a low-maintenance outdoor space with a cold plunge and sauna, and the best the city has to offer right at your doorstep. Light floods the house from every angle, and contrasting colours and materials create a striking first impression. On the main floor, you will find a powder room, a generous dining room, and a gorgeous over-sized kitchen with professional appliances and extensive storage space that overlooks the living room with views of the fully landscaped backyard. The outdoor space is low maintenance and thoughtfully laid out with a deck made for sun tanning, turf space for kids and pets to play and a cold plunge and sauna for the ultimate in rest and recovery. On the second floor ideal for kids or guests, there are three bedrooms, including the perfect home office, two beautiful bathrooms and a convenient oversized laundry closet with a stacked washer/dryer and a sink. The third floor is the perfect owners retreat with an oversized bedroom, walk-in closet, and hotel-inspired bathroom. A fully finished lower level with a recreation room, full bathroom and space roughed-in for an expansive laundry room completed the home. Live peacefully in this family-friendly enclave with parks, transit, and all the shops and restaurants Summerhill and Yorkville have to offer right at your doorstep. More details
    Listed by HARVEY KALLES REAL ESTATE LTD.
  • 501 78 Warren Road in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C12046876

    501 78 Warren Road Casa Loma Toronto M4V 2R6
    Main Photo: 501 78 Warren Road in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12046876
    $589,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C12046876
    Bedrooms:
    1
    Bathrooms:
    1
    Bright, Spacious and Totally Updated 1-Bedroom Corner Suite in Boutique Building. New Kitchen w/Brand New Stainless Steel Appliances, Vico Stone Countertops, Backsplash & Updated Cupboards. Completely New Bathroom Upgrade. New Floors Throughout and Freshly Painted Unit. A.620sqft with 480sqft Open Balcony. Located in a Fantastic Central Location. Just Steps to Clair Street Car or Short Walk to Yonge or Spadina Subway. Easy Access to Downtown, U of T , ROM, Walking Trails, Parks, Local Shopping, Loblaws and Forest Hill Village Shops. Sir Winston Churchill Park, Tennis Courts & Jogging Trails Close By. An Immaculately Maintained, Perfectly Managed Building w/On Site Live-in Super for Prompt Attention & Extra Security. Parking for 1-Car Underground, Storage Locker as Well As Property Tax & Free Laundry Facilities Are All Included in Low Maintenance Fees. This Is Not a Co-Op, Board Approval Not Needed. Wonderful Move-In Condition. More details
    Listed by RE/MAX REALTRON REALTY INC.
  • 308 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C12040676

    308 377 Madison Avenue Casa Loma Toronto M4V 3E1
    Main Photo: 308 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02)  : MLS®# C12040676
    $3,500
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C12040676
    Bedrooms:
    2
    Bathrooms:
    2
    South Hill on Madison is an ode to the Art Deco era, conveniently situated along the New Dupont! This two bedroom, two bathroom, north west corner suite offers two balconies and sunny clear views over Casa Loma. The open concept living space has floor-to-ceiling windows beside a sleek kitchen with a centre island, perfect for entertaining. the spacious bedrooms come equipped with closet organizers and a walkout to each of their own balconies. One underground parking and large private locker included. Top notch amenities include a party room with a kitchen and private dining space, a media room and an exercise room with yoga studio. More details
    Listed by ENGEL & VOLKERS TORONTO CENTRAL
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Data was last updated April 3, 2025 at 03:15 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.