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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  • 308 394 Avenue Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13232250

    308 394 Avenue Road Casa Loma Toronto M4V 2H4
    Main Photo: 308 394 Avenue Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02)  : MLS®# C13232250
    $2,495
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C13232250
    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.
  • 1204 155 St Clair Avenue W in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C13228346

    1204 155 St Clair Avenue W Casa Loma Toronto M4V 0A1
    Main Photo: 1204 155 St Clair Avenue W in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C13228346
    $3,595,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C13228346
    Bedrooms:
    3
    Bathrooms:
    3
    Welcome to the Avenue where Luxury meets distinction. When you step into this residence, originally designed by Brian Gluckstein, who also designed the building's elegant common areas, you are welcomed by a stylish foyer featuring a private elevator entry, coffered ceiling, & marble flooring, creating a grand first impression. Throughout the suite, every room is enhanced by elegant 9-ft coffered ceilings, adding architectural sophistication. The spacious living rm offers a gas fireplace, rich hrdwd flrs, built-in cabinetry and a seamless w/o to the balcony with north & west views ideal for entertaining & everyday comfort. The adjoining dining room overlooks the living rm & provides its own walk out allowing for an abundance of natural light. The gourmet kitchen w/custom cabinetry & b/i shelving showcases a sleek centre island w/marble countertops, hrdwd flrs & a versatile breakfast/family rm area that enhances functionality. Guests can use the elegant brand new 2-piece powder rm, beautifully renovated by Shaunn Lipsey Interior Design. For quiet moments, the den offers hrdwd flrs, a built-in bookcase, & elegant French doors making it a perfect retreat or home office. The split bedrm plan offers a primary suite w/a brand new spa like 5- piece ensuite bathroom also designed by Shaunn Lipsey Interior Design. 2 spacious walk-in closets & a walk-out balcony with north views. The second bedrm has its own 3-piece ensuite and a double closet. The well-appointed laundry room is equipped with a stacked washer/dryer, laundry sink, built-in shelving and ceramic flooring. Residents of the Avenue enjoy elite amenities including white glove full service concierge, valet parking, lounge, club rm w/full catering kitchen, spa and indoor swimming pool, gym, yoga/pilates room, and guest suites. Conveniently located just minutes from the boutiques of Yorkville, the charm of Forest Hill and in walking distance to Vibrant Yonge/St Clair & TTC. More details
    Listed by FOREST HILL REAL ESTATE INC.
  • 320 396 Avenue Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13219940

    320 396 Avenue Road Casa Loma Toronto M4V 2H5
    Main Photo: 320 396 Avenue Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02)  : MLS®# C13219940
    $2,095
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C13219940
    Bedrooms:
    1
    Bathrooms:
    1
    *** TWO FREE MONTHS on a 2 year lease or ONE MONTH FREE on a 1 year lease *** PLUS $1,000 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.
  • 2 11A Clarendon Avenue in Toronto: Casa Loma Condo Townhouse for sale (Toronto C02) : MLS®# C13223172

    2 11A Clarendon Avenue Casa Loma Toronto M4V 1H8
    Main Photo: 2 11A Clarendon Avenue in Toronto: Casa Loma Condo Townhouse for sale (Toronto C02)  : MLS®# C13223172
    $1,399,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C13223172
    Bedrooms:
    3
    Bathrooms:
    3
    Architectural, refined living on the south side of Clarendon in this prime Casa Loma community with a New York brownstone feel. Set among homes of wealth and character, this boutique condo of only 8 townhomes (with low maintenance fees!) offers generously-sized principal rooms and bedrooms on the entire upper main floor, gorgeous hardwood, high ceilings, and the bonus of over 800sf of finished lower level space. The living room is huge, tranquil and complete with plaster moldings, wood-burning fireplace and custom millwork and is open to the dining/family room for maximum versatility. Updated eat-in kitchen with brand new appliances. The primary bedroom is spacious, gracious and features a Juliette balcony, ensuite and wall-to-wall closet. The 2nd bedroom has ample storage with a full 2nd washroom beside it. This suite has no wasted space! The lower level makes for a great apartment or guest suite with separate side entry and a full kitchen, renovated 4 piece washroom, laundry, storage and a walkout to a patio. It is high quality, bright, work-at-home, work-out, hobby/studio space; or, relax and watch a movie in your media room for a quiet night at home. Garage parking for one car. Storage throughout the suite. Close to Yorkville, Spadina Village, Longo's, Summerhill Market, and the shops, restaurants and TTC at St. Clair and Yonge. Enjoy quiet residential living with the benefits of a condo lifestyle in this elegant and distinguished residence. Don't miss this unique opportunity! More details
    Listed by FOREST HILL REAL ESTATE INC.
  • 206 2 Clarendon Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13219936

    206 2 Clarendon Avenue Casa Loma Toronto M4V 1H9
    Main Photo: 206 2 Clarendon Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02)  : MLS®# C13219936
    $6,395
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C13219936
    Bedrooms:
    2
    Bathrooms:
    2
    *** TWO FREE MONTHS on a 2 year lease or ONE MONTH FREE on a 1 year lease *** PLUS $2,500 credit in 3rd month *** 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. 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.
  • 105 2 Clarendon Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13219944

    105 2 Clarendon Avenue Casa Loma Toronto M4V 1H9
    Main Photo: 105 2 Clarendon Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02)  : MLS®# C13219944
    $2,395
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C13219944
    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 *** 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.
  • 506 155 St Clair Avenue W in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C13219706

    506 155 St Clair Avenue W Casa Loma Toronto M4V 0A1
    Main Photo: 506 155 St Clair Avenue W in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C13219706
    $3,250,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C13219706
    Bedrooms:
    3
    Bathrooms:
    3
    This is the condo that checks virtually every box. Almost 2,400 sq ft of luxury living space plus a huge 580 sq ft terrace. South and west views catch an abundance of natural sunshine. The terrace is equipped with both a gas line for a BBQ plus a hose bib for your gardening. Inside, two spacious bedrooms both with walk outs to the 350 sq ft Balcony. The primary bedroom contains two walk in closets, built ins, motorized window blinds and a 5 piece bathroom. The spacious second bedroom maintains a 4 piece ensuite bathroom and a walk out to the balcony. A good size den/office is perfect for those wishing to work from home. The designer kitchen boasts a sub zero fridge, wolf ovens and cook top and a miele dishwasher. A convenient sliding door allows for breakfast on the balcony or terrace. The palatial living/dining areas are accented by a 9 foot ceiling, pot lights, gas fireplace and a walkout to the terrace. The terrace of suite 506 is what truly makes this property special. South and west facing and open to the heavens! The combined living and dining areas will ensure plenty of space for major family events. Suite 506 contains both plenty of storage within the unit plus a large external storage locker. The building maintains many features that one would come to expect. Valet parking, and indoor swimming pool and hot tub, an outstanding gym, yoga room and of course a party room with a large functional kitchen for all of your events. More details
    Listed by WEISS REALTY LTD.
  • 109 275 MacPherson Avenue in Toronto: Casa Loma Commercial for sale (Toronto C02) : MLS®# C13213842

    109 275 MacPherson Avenue Casa Loma Toronto M4V 1A4
    Main Photo: 109 275 MacPherson Avenue in Toronto: Casa Loma Commercial for sale (Toronto C02)  : MLS®# C13213842
    $729,900 /For Sale
    Commercial
    Status:
    Active
    MLS® Num:
    C13213842
    Major Bus.:
    Service Related
    Total Area:
    612 sq. ft.
    Rare opportunity to own affordable office space in an exceptional Midtown location. Situated on the ground floor of the prestigious boutique Macpherson Design Centre, just west of Avenue Road in the affluent Republic of Rathnelly neighbourhood, this sophisticated commercial space is within walking distance to Designers Walk, Yorkville, and the Mink Mile. Designed for a professional practice or creative business, the space features a rare large south-facing private outdoor garden/yard complete with storage shed - an extraordinary feature seldom found in office properties. Beautifully renovated with over $100,000 in upgrades, the unit offers clear-span space with no columns, soaring 10-foot ceilings, internal security cameras, central speaker system, and prewired networking throughout. Beautifully appointed with a kitchenette and private washroom, this turnkey space is ready for immediate occupancy. Front-door parking is available by City permit (fee applicable), with Green "P" parking conveniently located next door and transit just steps away. An outstanding opportunity for business owners looking to own instead of lease, while enhancing both their long-term investment value and professional presence. Vendor will consider a VTB, Vendor take back mortgage. More details
    Listed by HARVEY KALLES REAL ESTATE LTD.
  • 414 396 Avenue Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13210476

    414 396 Avenue Road Casa Loma Toronto M4V 2H5
    Main Photo: 414 396 Avenue Road in Toronto: Casa Loma Condo Apartment for lease (Toronto C02)  : MLS®# C13210476
    $1,695
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C13210476
    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.
  • 381 Madison Avenue in Toronto: Casa Loma House for lease (Toronto C02) : MLS®# C13206116

    381 Madison Avenue Casa Loma Toronto M4V 2W7
    Main Photo: 381 Madison Avenue in Toronto: Casa Loma House for lease (Toronto C02)  : MLS®# C13206116
    $12,900
    Residential Freehold
    Status:
    For Lease
    MLS® Num:
    C13206116
    Bedrooms:
    4
    Bathrooms:
    5
    Exclusive, Stunning & Chic Residence Located In The Sought-After Casa Loma Neighborhood! This 4Bedroom, 5 Bathroom Semi- Detached Home Is Beautifully Designed With High-Quality Finishes And An Abundance Of Natural Light Throughout. Boasting A Modern Kitchen With Walk-Out To A Spectacular Oversized Private Patio - Perfect For Entertaining, Bright Living Area With Custom Built-Ins, Led Lighting, Sleek Gas Fireplace, Staircase With Wrought-Iron Railing Details, Elevator, High-Ceilings, Master Retreat With Large Walk-In Closet And Spa-Like Ensuite With Luxurious Double Entry Frameless Shower And Soaker Tub, Private Rooftop Terrace, 1 Car Garage Parking And Many More Upgrades! Steps To Top Amenities And Ttc, A Walker's Paradise With A Score Of 90. You Don't Want To Miss This One! More details
    Listed by PSR
  • 738 Huron Street in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C13195494

    738 Huron Street Casa Loma Toronto M4V 2W3
    Main Photo: 738 Huron Street in Toronto: Casa Loma House for sale (Toronto C02)  : MLS®# C13195494
    $1,885,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C13195494
    Bedrooms:
    4
    Bathrooms:
    3
    Beautifully maintained and thoughtfully renovated, this wide brick semi-detached home offers a blend of original character and modern function, with a sun-filled main floor family room addition, large finished third-floor loft, flexible lower-level living space, mature private gardens, and legal front pad parking. Rich in charm, the main floor features restored leaded glass windows, refinished hardwood, crown mouldings, and elegant formal principal rooms. The spacious living room with decorative fireplace flows into a formal dining room, creating a sophisticated setting for entertaining. At the rear, a stunning family room addition with exposed brick, gas fireplace, powder room, and striking black wrought-iron French doors opening to the private garden. The bright kitchen offers excellent storage, black stone countertops, white subway tile backsplash, stainless steel appliances, and an eat-in area with lovely sight-lines. Upstairs, the generous primary bedroom features wall-to-wall closets, built-in drawers. A spacious second bedroom overlooks the streetscape, while the family bath includes a glass shower, soaker tub, and vanity storage. A spiral staircase leads to the finished third-floor loft, a bright and versatile space with good ceiling height, skylight, large window, and knee-wall storage, and lovely Casa Loma views. The lower level includes a separate side entrance, a 3-piece bath, excellent storage, and flexible living space perfect for guests, teens, a home office, or nanny/in-law potential. Outside, the rear garden feels like a hidden escape in the heart of the city, with flagstone, mature plantings, and exceptional privacy. Live in the heart of the city at the foot of Casa Loma. Steps to Dupont Subway Station, well positioned between Downtown and Midtown- walking distance to the shops and restaurants and amenities in Yorkville, the Annex and Yonge & St Clair. 15min drive to the Allen Expwy. Top rated public and private schools including Brown & Deer Park. More details
    Listed by ROYAL LEPAGE REAL ESTATE SERVICES LTD.
  • 21 260 Russell Hill Road in Toronto: Casa Loma Condo Townhouse for sale (Toronto C02) : MLS®# C13203512

    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®# C13203512
    $3,750,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C13203512
    Bedrooms:
    4
    Bathrooms:
    6
    Townhouse 21 at 260 Russell Hill Road is Nestled Within A Park Garden Setting On Winston Churchill Park, In The Heart Of South Hill - One Of Toronto's Most Quietly Exclusive Enclaves. Extremely Rare West-Facing & Perfectly Positioned At The Center Of Its Development, This Is A Residence That Captures Unobstructed Sunsets Over The Park Every Evening. A Private Balcony Off The Second Floor Extends That Relationship Further: Open Sky, Open Canopy, Entirely Yours. This Is An Address That Cannot Be Replicated or Stumbled Upon. It Is Arrived At Deliberately, By Those Who Know Exactly What They Are Looking For. Originally Conceived As A Designer's Own Home, This Four-Bedroom, Six-Bathroom Residence - Three Ensuite - Spans 3,500 Sq Ft Across Four Levels With Soaring Ceilings Throughout. Two Oversized Skylights Flood The Home With Natural Light, Illuminating The Custom Stark Needlepoint Carpet On The Circular Staircase. Oak Hardwood Floors Run Across Three Levels. Paneling, Crown Molding, And Millwork Throughout. The Custom Marble Kitchen Features Professional-Grade Gas Burners & Stainless Steel High-End Integrated Appliances. Gas Fireplace In The Family Room. The Third Floor Primary Suite Offers A Jacuzzi Tub, High-End Built-In Closets, And A Private office. Private Elevator Services All Four Floors. Two Underground Parking Spaces With Direct Entry Complete The Picture. To The Rear, A Walled Garden Oasis With A Gas Line For The BBQ - Private, Still, And Entirely Unexpected. This Home Asks Nothing Of You Except That You Bring Your Life Fully Into It - The Heirloom Pieces, The Crystal, The Art Gathered Across Decades. No Compromise. No Sacrifice. Every Cherished Piece Finds Its Place. For Those Who Already Have The Cottage, The Second Home, The Other Life - and The Discernment To Recognize When Something Irreplaceable Is In Front Of Them. A Home Of Genuine Provenance, In A Location That Will Never Be Reproduced. Fully Secure. Effortlessly Maintained. Utterly Unrepeatable. More details
    Listed by HARVEY KALLES REAL ESTATE LTD.
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Data was last updated June 3, 2026 at 06:15 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.