South Hill on Madison | 377 Madison Avenue, Toronto

In the shadow of Toronto's magnificent Casa Loma stands a residential masterpiece that beautifully balances contemporary design with neighborhood heritage. Completed in 2017, South Hill on Madison rises 7 stories at 377 Madison Avenue, housing 159 thoughtfully designed residences that blend sophisticated aesthetics with premium comforts. The building's distinctive curved architecture and limestone-inspired façade create a respectful dialogue with the historic surroundings while establishing its own refined identity in this prestigious neighborhood.

What distinguishes South Hill on Madison is its commitment to boutique luxury living at a human scale. The architectural design features fluid curves that give the building a sense of movement and grace, standing as a contemporary counterpoint to Casa Loma across the way. The mid-rise scale maintains the intimate character of the neighborhood while providing residents with a full complement of amenities typically found only in larger developments. Each detail has been considered to create living spaces that are both aesthetically pleasing and functionally superior.

Signature Features

Distinctive Architecture: The building's curved design and limestone-inspired façade create a sophisticated presence that respects the historic character of the Casa Loma neighborhood
Boutique Scale: With only 7 stories containing 159 residences, the building offers an intimate living experience rarely found in Toronto condominiums
Prime Location: Situated steps from the historic Casa Loma grounds and gardens, with easy access to Dupont subway station and the vibrant amenities of midtown Toronto
Outdoor Living: Every residence features at least one private balcony, with select units offering expansive terraces or rooftop spaces with breathtaking city views
European-Inspired Finishes: Interiors showcase streamlined European cabinetry, quartz countertops, and porcelain tile accents for a refined aesthetic
Nine-Foot Ceilings: Generous ceiling heights create an enhanced sense of space and light throughout the residences

The living spaces at South Hill on Madison range from approximately 384 to 1,862 square feet, with configurations from efficient one-bedroom layouts to generous two-bedroom plus den residences. Each home features thoughtful design elements including engineered laminate flooring, floor-to-ceiling windows that maximize natural light, and spa-inspired bathrooms with distinctive rain-style shower heads. Kitchens combine form and function with sleek European cabinetry, quartz countertops, and energy-efficient appliances that elevate the daily cooking experience.

Amenities

24-hour concierge
Fully-equipped fitness center
Dedicated yoga studio
Party room for entertaining
Cinema/media room
Common rooftop deck with panoramic views
Visitor lounge
Visitor parking

The location offers an exceptional balance of urban convenience and neighborhood charm. Residents enjoy proximity to the historic Casa Loma castle and gardens—perfect for weekend explorations or attending seasonal events. The vibrant stretch of Dupont Street provides everyday conveniences including grocery shopping at Loblaws, pharmacy needs at Shoppers Drug Mart, and wine selection at LCBO. Dupont subway station is within easy walking distance, connecting residents to Toronto's extensive transit network.

South Hill on Madison represents a refined approach to city living—where boutique scale, thoughtful design, and a prestigious address create a residential experience of uncommon quality. For those who appreciate sophisticated aesthetics, premium finishes, and a location that balances historic character with urban convenience, this address offers a distinctive living experience in one of Toronto's most coveted neighborhoods.