135 Madison Avenue

Annex, Toronto, M5R 2S3
FOR SALE
$3,650,000
135 Madison Avenue, Toronto
135 Madison Avenue
135 Madison Avenue
135 Madison Avenue
135 Madison Avenue
135 Madison Avenue
135 Madison Avenue
135 Madison Avenue
135 Madison Avenue
135 Madison Avenue
135 Madison Avenue
135 Madison Avenue
135 Madison Avenue
135 Madison Avenue
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6
BEDROOMS
5
BATHROOMS
3
KITCHENS
12 + 1
ROOMS
C12952628
MLSID
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Property Description
This grand dame home sits on the iconic Madison Avenue in the prime Annex. Circa 1905, 135 Madison Avenue is just under 4,000 square feet above grade and filled with original character including 4 fireplaces, original trim, wainscoting, crown moulding, and stained glass windows. The well proportioned house features 9.5' ceilings on the main floor, a large formal living room, dining room, an oversized kitchen with a butlers pantry, and a beautiful main floor family room that leads out to the lush garden. On the second floor you will find a generous primary bedroom with a sitting area, fireplace and a three piece ensuite. There are an additional 3 large bedrooms on the second floor as well as 3 full washrooms, a dedicated laundry room, kitchen, and a large sunny deck. The third floor would make a fabulous primary suite and currently includes a spacious living room, kitchen, two additional bedrooms, one full washroom, and a large deck with skyline and treetop views. The basement is partially finished with 7 foot ceilings and features a separate side door entrance. This home flows nicely as single family, which it has been used as for many years, but has potential for other layouts and possibilities including converting the property back into multiple units. Two car private drive parking and garden suite potential. The Annex speaks for its self with easy TTC, fabulous shops, restaurants, parks and schools. Floor plans attached to listing. Offers anytime. Great opportunity for those looking for a co-ownership property!
Nearby Intersections
Property Features
Fenced Yard, Library, Park, Public Transit, Rec./Commun.Centre, School, Water Heater, Private, Living Room
Property Details
Address
135 Madison Avenue
Community
Postal Code
M5R 2S3
Property Type
Detached, Detached
Lot Size
33' x 126'
Taxes
$18,814 (2025
Basement
Partially Finished
Exterior
Deck, Patio, Porch
Heat Type
Water
Heat Source
Gas
Water
Municipal
Parking Spaces
2
Garage Type
None
Listing contracted with Bosley Real Estate Ltd.
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$2,795,000
FOR SALE
Gorgeous Lawrence Park classic five bedroom centre hall plan with gracious principal rooms - perfect for entertaining! Live in a beautiful five-bedroom home on a 50' frontage for under $2.8M! Spacious living room with fireplace, sunny west-facing windows and hardwood floors. Main floor office or den enveloped in windows overlooking the backyard. Dining room is open to an updated kitchen with an eating bar, great light and excellent storage. There is also a built-in desk with granite countertops! On the second floor, the primary bedroom has a sitting area to enjoy your morning coffee, a large sleeping area, two huge double closets with custom closet organizers and a beautiful five-piece ensuite bathroom with heated floors. Two more bedrooms and a full four-piece renovated bathroom complete the second level. The third floor has two more spacious bedrooms and a renovated three-piece bath.The lower level has recently all been redone, with a large recreation room, a playroom, an updated two-piece bathroom and a separate laundry and storage room. There is a fully fenced yard with a gate in the driveway to keep dogs and little ones safe! Private drive and an oversized single (1.5) detached garage with abundant storage. This beautiful and spacious home has undergone many renovations - three new bathrooms, new space pak central air system, new natural gas BBQ line, freshly painted, fully renovated basement and more! Easy walk to Bedford Pk Jr + Sr school and several top private schools too! Located steps to the subway, the shops and restaurants on Yonge Street, this home is a very special offering for a most discerning buyer!
38 Purdon Drive, Toronto
5+2
BEDS
5
BATHS
$2,758,888
FOR SALE
A rare fusion of modernist architecture and natural ravine beauty, this custom-built residence at 38 Purdon Dr sits on a 60x200 ft lot with discreet access to protected parkland and a natural creek trail. Designed in the mid 1960s by a local architect and fully transformed in 2002 and 2024 under professional design supervision, the home features approx. 5000 sqft across 3.5 levels, constructed with fire-resistant concrete block, full brick cladding, and structural steel beams.The sun-filled interior showcases 5+2 bedrooms, 5 bathrooms, 2 full kitchens, and 4 entrances, offering flexibility for multigenerational living, work-from-home needs, or extended family use. Custom millwork, solid oak staircases, and soaring ceilings blend with upgraded finishes like engineered hardwood, porcelain tile, and integrated lighting. The primary suite includes a skylight ensuite, walk-in closet, and access to a private upper deck with seasonal ravine views.The main level kitchen and sunroom overlook a fully landscaped backyard oasis, featuring a designer rainwater-fed waterfall with recirculating stream, programmable LED lighting, fire pit, mature trees, and multi-level decks perfect for entertaining. An oversized double garage fits 2 SUVs plus storage; the self-draining driveway accommodates 8 to 9 cars.Efficiency and smart upgrades abound: 3-zone RBI hydronic heating, dual A/C systems, 17kW backup generator with auto transfer switch, 200A panel, programmable irrigation, and Wi-Fi-enabled garage opener. Basement includes sauna, whirlpool tub, separate entry, and potential for private suite (*not retrofitted, buyer to verify*). Rear small gate connects to forested parkland and trail system maintained by TRCA.A unique opportunity to own a timeless structure, reimagined for modern livingwith the privacy, up scale, and craftsmanship rarely found in today's market.
170 Fenn Avenue, Toronto
5+1
BEDS
4
BATHS
$2,750,000
FOR SALE
Experience the pinnacle of North York living in the prestigious St. Andrew-Windfields community. This exceptional property on Fenn Avenue is nestled within a lush, mature landscape characterized by quiet streets and an impressive tree canopy, offering a serene escape that remains remarkably central. Families will appreciate being within the catchment of top-tier schools, including Owen Public School and York Mills Collegiate Institute, while also enjoying proximity to elite private academies like Bayview Glen or the Toronto French School. This meticulously maintained two-storey detached residence offers over 3,000 square feet of total living space on a premium 50 by 120-foot south-facing lot. Combining the character of a classic home with the finishes and quality of a newer build, the interior features rich hardwood flooring throughout and an abundance of natural light streaming through expansive windows. The thoughtful layout provides a seamless visual connection between the indoor living spaces and the lush outdoor scenery. At the heart of the home, the chef-inspired kitchen boasts granite countertops, high-end stainless-steel appliances, and extensive cabinetry, making it as functional as it is beautiful. The second floor is perfectly designed for large families, offering five spacious bedrooms and two well-appointed bathrooms, while the lower level offers a massive recreation room, an additional bedroom, and ample storage. The property's true highlight is the private, fully fenced garden, where a majestic maple tree provides shade over two separate terraces. This outdoor sanctuary offers a peaceful retreat for quiet afternoons or an idyllic setting for large gatherings with friends & family. Residents enjoy unparalleled convenience with the option of walking to the Bayview & York Mills plaza, and easy access to public transportation. This home perfectly balances sophisticated suburban tranquility with elite metropolitan connectivity.
243 Burbank Drive, Toronto
5+2
BEDS
6
BATHS
$3,498,888
FOR SALE
Stunning "Cottage-view " ravine property nestled on a quiet street with no through traffic in the city. This custom-built 5331 sqft (MPAC) above-grade home features a dramatic curved design that maximizes tranquil ravine views, with most rooms overlooking the greenery.Boasting a grand façade with a circular driveway on an 80 ft frontage, well-maintained, bright, and spacious two-level residence includes a fully finished two-level basement with a separate entrance-ideal for large families or generating rental income.Modern updated kitchen with Miele stainless steel appliances, a built-in double-door fridge, a character-filled recreation room with wet bar, oak paneling, hardwood flooring throughout, and multiple walkouts to sun decks and patio overlooking the ravine.The oversized primary bedroom features a luxurious 5-piece ensuite. Additional highlights include a second kitchen in the basement, mudroom, custom drapery, crown moulding, fireplace, wainscoting, pot lights, cedar closet, and chandelier. Located in top-ranked school districts, close to Earl Haig Secondary School and Bayview Middle School. A rare, one-of-a-kind ravine home offering privacy, space, and exceptional design.
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