2017

Year Built

159

Number of Units

7

Storeys

Neighbourhood

Casa Loma

Developer

Burnac Corporation

You'll Love

Tarragon Theatre. This intimate stage hosts original and inspiring Canadian plays, just a short stroll from home!

Highlights

High ceilings. Nice amenities. Private balcony views.

Tell me more about South Hill on Madison

South Hill on Madison is an attractive mid-rise residence in Casa Loma neighbourhood. Nestled in a lush area at 377 Madison Avenue, this building is steps from the historic grounds of Casa Loma itself. Tour the gardens and passageways, or attend the exciting year-round events at this beloved Toronto landmark. South Hill condos are also close to cozy pubs and cafes on Dupont, and live theatre in The Annex. The Casa Loma condos for sale at 377 Madison Avenue have 9 foot high ceilings, quartz countertops, energy efficient appliances, and engineered laminate flooring. They also have large windows and private balconies overlooking the incredible area surrounding the building. Amenities at South Hill on Madison include a concierge, a gym, yoga studio, media room, party room, and a rooftop deck. Walk to nearby parks and parkettes for pleasant afternoons outside. Or, meet a friend at a rooftop patio on Dupont to listen to live music. There are also schools, museums, and Dupont subway station nearby. If you're looking for a home in a desirable area with a rich history and vibrant present, South Hill on Madison condos could be a perfect fit!

Amenities

Events/Meeting Room

Gym

Rooftop Deck/Outdoor Patio

Media Room

Concierge

377 Madison Ave For Sale

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  • 510 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13659546

    510 377 Madison Avenue Casa Loma Toronto M4V 3E1
    Main Photo: 510 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13659546

    510 377 Madison Avenue Toronto M4V 3E1 Casa Loma

    $3,250
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C13659546
    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 REALTY ASSOCIATES INC.
    LISTING DETAILS
    JARROD ARMSTRONG

  • in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13821200

    Contact for address
    Main Photo: in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C13821200

    Contact for address details

    $3,900
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C13821200
    Bedrooms:
    1
    Bathrooms:
    2
    Beautifully Furnished Short term rental, 1BR 2 Baths. Ideal for executives. Exclusive boutique building nestled at the foot of Casa Loma. Tucked away among mature trees, this elegantly appointed suite offers a peaceful retreat from the city while being just steps to Dupont Subway Station and a short walk to Yorkville, Summerhill, and The Annex. Enjoy the perfect balance of tranquil surroundings and urban convenience.The space is beautifully furnished, 1-bedroom and full 2-baths, ideal for anyone seeking a turnkey, short-term residence. Featuring 9-foot smooth ceilings and a bright, open-concept layout, the suite is thoughtfully designed. A contemporary kitchen showcases quartz countertops, an undermount sink, abundant cabinetry, a versatile island with breakfast bar, and premium built-in stainless steel appliances. Impeccably managed building offering 24-hour concierge and security, a fully equipped fitness centre with yoga studio, party room, media room, visitor parking, and bicycle storage. Steps from Dupont Subway Station, Casa Loma, scenic parks, George Brown College, and the vibrant shops and restaurants along Dupont, with easy access to Yorkville and the city's finest amenities including, University of Toronto, Major Hospitals, Bay & Bloor, ROM & Kroener Hall. Available furnished for a 5-month lease, December 1st through April. More details
    Listed by SUTTON GROUP-ADMIRAL REALTY INC.
    LISTING DETAILS
    JARROD ARMSTRONG

  • 216 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C14110984

    216 377 Madison Avenue Casa Loma Toronto M4V 3E1
    Main Photo: 216 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C14110984

    216 377 Madison Avenue Toronto M4V 3E1 Casa Loma

    $2,095
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C14110984
    Bedrooms:
    1
    Bathrooms:
    1
    CASA LOMA LIVING. SMART DESIGN. BOUTIQUE STYLE. Welcome to South Hill on Madison, a contemporary Art Deco-inspired boutique residence tucked into one of Toronto's most distinctive neighbourhoods at the foot of Casa Loma, where South Hill, Forest Hill, Yorkville and The Annex come together. This stylish suite delivers one of the smartest layouts in its class, with a defined bedroom area that creates separation from the main living space while maximizing functionality. The sleek kitchen features Caesarstone counters and built-in appliances, while thoughtful upgrades and space-saving features include a built-in desk, drop-down dining table, custom roller blinds and ensuite laundry. Designed for modern living, the flexible layout offers the freedom to create a space that reflects your lifestyle, whether you're working from home, relaxing or entertaining. Step outside to your private north-facing balcony, or unwind in the beautifully finished bathroom with marble details and a glass-enclosed shower. **The lifestyle extends well beyond your front door.** Just steps from Suite 216, the media room offers a welcoming extension of your living space, ideal for relaxing, watching a movie or enjoying a change of scenery. The gym is equally convenient, with both amenities located on the same level and no elevator or stairs required to access either. The building also features a stylish party room with terrace, offering another inviting setting to gather and entertain, along with concierge service and visitor parking. Leave the car behind! Dupont Subway Station is nearby, along with George Brown Polytechnic's Casa Loma Campus, neighbourhood cafés, restaurants, parks and everyday conveniences. An exceptional opportunity to enjoy sophisticated, intelligently designed Toronto living in a distinctive boutique setting. More details
    Listed by EXP REALTY
    LISTING DETAILS
    JARROD ARMSTRONG

  • 502 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C14120428

    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®# C14120428

    502 377 Madison Avenue Toronto M4V 3E1 Casa Loma

    $598,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C14120428
    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
    JARROD ARMSTRONG

  • 412 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C14127468

    412 377 Madison Avenue Casa Loma Toronto M4V 3E1
    Main Photo: 412 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02) : MLS®# C14127468

    412 377 Madison Avenue Toronto M4V 3E1 Casa Loma

    $699,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C14127468
    Bedrooms:
    2
    Bathrooms:
    2
    Stylish South Hill Suite. Welcome to this thoughtfully designed 2-Bedroom, 2-Bathroom suite offering abundant in-suite storage and upgrades throughout. Designer kitchen features Carrara Marble countertops and backsplash, high-gloss cabinetry with soft-close drawers and a custom island with built-in dining table for four. Rich Sumo Antique Engineered Hardwood Flooring runs throughout the Living Room and Bedrooms. Primary Bedroom includes a wall-to-wall closet with built-ins and an upgraded 3-piece ensuite. The spacious and versatile 2nd bedroom offers flexibility to fit your lifestyle needs. The main 4-piece bathroom is conveniently located just across from the 2nd bedroom. Enjoy beautiful northern views of the treetops and the iconic Casa Loma turret from every window. The unit comes with a combined parking spot and private storage locker conveniently located just steps from the elevator lobby. The building offers 24 hour concierge service, gym, steam room, party room, media lounge and pet spa. Located in the desirable Brown Jr PS district. Mere steps to Dupont Station and an easy walk to local parks, green spaces and the vibrant shops and restaurants of the Annex and Yorkville. More details
    Listed by RE/MAX PRIME PROPERTIES - UNIQUE GROUP
    LISTING DETAILS
    JARROD ARMSTRONG

  • 714 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C14154928

    714 377 Madison Avenue Casa Loma Toronto M4V 2W7
    Main Photo: 714 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for lease (Toronto C02) : MLS®# C14154928

    714 377 Madison Avenue Toronto M4V 2W7 Casa Loma

    $3,500
    Residential Condo & Other
    Status:
    For Lease
    MLS® Num:
    C14154928
    Bedrooms:
    2
    Bathrooms:
    2
    *ALL INCLUSIVE* Proudly presenting this exquisite 2-bedroom, 2-bathroom penthouse at South Hill on Madison, offering just under 900 sq. ft. of thoughtfully designed living space. Featuring a spacious, open-concept living and dining area with unobstructed east-facing views, this residence seamlessly blends contemporary elegance with everyday comfort. The beautifully appointed, modern kitchen showcases top-of-the-line appliances and refined custom finishes, creating the perfect setting for entertaining. Step outside to your private terrace oasis with breathtaking views. Nestled in the coveted Casa Loma community, this address offers a rare blend of urban convenience and established, tree-lined charm, just minutes from parks, boutique shops, and transit. Enjoy the quiet, walkable surroundings while remaining effortlessly connected to the best of midtown Toronto. More details
    Listed by HOUSESIGMA INC.
    LISTING DETAILS
    JARROD ARMSTRONG
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Data was last updated November 8, 2026 at 02:15 PM (UTC)
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.

To find out more about South Hill on Madison Condos for sale or for rent at 377 Madison Ave, and other Toronto condos for sale in Casa Loma neighbourhood, contact us.

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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.