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.

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314 377 Madison Avenue
Casa Loma Toronto M4V 3E1

$749,900
Residential Condo & Other beds: 2 baths: 2.0

Main Photo: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 1: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 2: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 3: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 4: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 5: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 6: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 7: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 8: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 9: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 10: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 11: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 12: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 13: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 14: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 15: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 16: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 17: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 18: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 19: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 20: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 21: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 22: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 23: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 24: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 25: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 26: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 27: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 28: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 29: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 30: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 31: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Photo 32: 314 377 Madison Avenue in Toronto: Casa Loma Condo Apartment for sale (Toronto C02)  : MLS®# C12345263
Status:
Active
Prop. Type:
Residential Condo & Other
MLS® Num:
C12345263
Bedrooms:
2
Bathrooms:
2
Unique opportunity to own a stunning boutique condo in one of Torontos most desirable neighborhoods, right by Casa Loma. This exceptional 2-bedroom, 2-bathroom home offers an exquisite blend of luxury, charm, and convenience. From the modern, open-concept layout to the high-end finishes, every detail has been carefully crafted. Large windows bring in abundant natural light, while the spacious bedrooms and elegant bathrooms provide comfort and style. Located near Torontos historic Casa Loma, this condo is close to vibrant dining, shopping, and cultural destinations, with easy access to transit options that connect you seamlessly to the city. If you're looking for an urban oasis that combines both prestige and practicality, this is it. Dont miss out on this rare find its the perfect place to call home. EXTRAS: Experience the luxury of South Hill on Madison Condos, offering a range of premium amenities such as a fitness center, rooftop lounge with stunning views, private parking, and secure access for ultimate convenience and comfort.
Property Type:
Residential Condo & Other
Property Sub Type:
Condo Apartment
Home Style:
Apartment
Total Approx Floor Area:
800-899
Exposure:
East
Bedrooms:
2
Bathrooms:
2.0
Kitchens:
1
Bedrooms Above Grade:
2
Kitchens Above Grade:
1
Rooms Above Grade:
5
Heating type:
Forced Air
Heating Fuel:
Gas
Storey:
14
Balcony:
Open
Basement:
None
Fireplace/Stove:
No
Garage:
Underground
Garage Spaces:
1.0
Parking Features:
None
Parking Type:
Exclusive
Parking Spaces:
0
Total Parking Spaces:
1.0
Parking Spot #1:
B #40
Locker:
None
Family Room:
No
Possession Details:
30/60/90
HST Applicable To Sale Price:
Included In
Maintenance Fee:
$783.97
Maintenance fees include:
Heat Included, Water Included, CAC Included, Common Elements Included, Building Insurance Included
Taxes:
$4,313.19 / 2024
Assessment:
$- / -
Toronto C02
Casa Loma
Toronto
Hospital, Library, Park, Place Of Worship, Public Transit, School
Other
Security Guard
Restricted
Existing fridge, electric stove, dishwasher, washer and dryer and all ELFs
Concrete
Concierge, Gym, Party Room/Meeting Room, Rooftop Deck/Garden, Visitor Parking
Floor
Type
Size
Other
Flat
Living Room
24'6⅞" × 13'6"
Laminate, Open Concept, W/O To Balcony
Flat
Dining Room
24'6⅞" × 13'6"
Laminate, Open Concept, Combined w/Kitchen
Flat
Kitchen
24'6⅞" × 13'6"
Laminate, Open Concept, Stainless Steel Appl
Flat
Primary Bedroom
10'6" × 10'1"
Laminate, 4 Pc Ensuite, Walk-In Closet(s)
Flat
Bedroom
10'6" × 8'2"
Laminate, 3 Pc Ensuite, B/I Closet
Flat
Laundry
Measurements not available
Flat
Foyer
Measurements not available
Special Designation:
Unknown
Air Conditioning:
Central Air
Central Vacuum:
No
Seller Property Info Statement:
No
Laundry Access:
Ensuite
Condo Corporation Number:
2681
Property Management Company:
ICC Property Management Ltd.
Date Listed:
Aug 14, 2025
Original Price:
Previous Price:
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Listed by HARVEY KALLES REAL ESTATE LTD.
Data was last updated August 15, 2025 at 01:15 PM (UTC)
Area Statistics
Listings on market:
37
Avg list price:
$1,038,800
Min list price:
$439,900
Max list price:
$5,450,000
Avg days on market:
51
Min days on market:
1
Max days on market:
723
These statistics are generated based on the current listing's property type and located in Casa Loma. Average values are derived using median calculations. This data is not produced by the MLS® system.
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.