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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5+1
BEDS
4
BATHS
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$3,495,000
FOR SALE
Welcome To 18 Swansdown Drive, A Gracious Ravine Side Residence Set On A Quiet Cul De Sac That Is St. Andrew's Best Kept Secret. Owned By One Family Since Built, This Beautifully Maintained Home Offers Approx. 5,410 Sq.Ft. Of Finished Living Space Across Three Levels, With 5 Bedrooms, 4 Bathrooms, An Attached Two Car Garage Plus A Private Double Driveway. Large Principal Rooms Feature Traditional Millwork, Hardwood Flooring, Crystal Chandeliers, Designer Wallcoverings, Crown Moulding, Wainscotting Plus Its Timeless French And English Inspired Detailing Will Leave You In Awe. The main floor features a formal living room with neoclassical mantel and marble inlay gas fireplace, directly connected to an elegant dining room. A generous chef's kitchen with breakfast area walks out to an upper balcony overlooking a swoonworthy, picturesque ravine. The family room with floor to ceiling built ins and private main floor office bring sophistication and function to everyday living, while the powder room and mudroom with side entry add practical versatility. The second floor offers five bedrooms, including a spacious primary suite with walk in closet and en-suite bathroom, plus well proportioned bedrooms with excellent closet space and treed outlooks. The Finished Walk Out Lower Level Is Ideal For Entertaining, Multigenerational Living Or Extended Family Use, With A Large Recreation Room, Floor to Ceiling Muskoka Stone Wood Burning Fireplace and a Wet Bar. Top it all off with a Billiard Room, Office, Laundry, Bathroom Plus Direct Access To The Rear Yard. This Home Has It All, Set On A Spectacular Deep Ravine Lot With Mature Trees, Professional Landscaping, Irrigation System, Cedar Hedges plus an Upper Balcony And Lower Flagstone Patio Provides For Multi Level Outdoor Entertaining. Close To Top Schools Including Dunlace P.S., Windfields, York Mills Collegiate, Parks, Transit, Oriole GO, 401 And DVP. A Rare Opportunity To Own A Substantial Family Home In A Peaceful Ravine Enclave.
51 Indian Grove, Toronto
6+1
BEDS
4
BATHS
$3,295,000
FOR SALE
51 Indian Grove is a grand and storied High Park residence - a rare opportunity to acquire substantial frontage on one of the neighbourhood's most beautiful and prestigious streets. Set on an effective 65-foot-wide lot - with 55 feet of frontage plus an additional 10-foot shared driveway - the property offers more than 5,000 sq. ft. of existing living space within a solid, historic structure. Enjoy it as-is, restore its original character, reimagine the interiors, or create a remarkable new custom home in one of High Park/Roncesvalles' most coveted settings. A rare offering with scale, presence, history, and extraordinary potential.
35 Bywood Drive, Toronto
5
BEDS
4
BATHS
$3,249,900
FOR SALE
Renovated luxury home in the heart of Rosethorn Park, set on a quiet, tree-lined street just steps to top-rated schools, Thorncrest Plaza, TTC, and neighbourhood parks. This meticulously maintained and extensively improved two-storey home offers over 5,400 sq ft of total living space (including the basement), featuring 5 excellent-sized bedrooms, 4 bathrooms, and a thoughtfully refreshed custom eat-in kitchen with new flooring, new stone counter and backsplash, and newer stainless steel appliances. Bright and well-appointed principal rooms, including a large living room, a separate dining area with front-facing windows, a main floor family room with a bay window overlooking the rear patio and pool, and a private office that can be converted into a 6th bedroom. The extensively renovated basement features a spacious rec room with a wet bar, a dedicated exercise room, a large laundry room with ample storage, temperature-controlled storage, and a separate side entrance (potential for a lower-level apartment). Relax and enjoy the benefits of the rear yard oasis, complete with a large inground concrete heated pool with updated equipment, hot tub, stone patio, gazebo, and a large landscaped side yard.
11 Montressor Drive, Toronto
5
BEDS
4
BATHS
$3,050,000
FOR SALE
Rare opportunity to acquire a premium ravine-backed property in the heart of St. Andrew-Windfields. Situated on an approximately 12,800 sq. ft. lot, this property offers exceptional privacy, a deep rear yard, and a natural ravine setting rarely available in this pocket. The existing home can be renovated to create a comfortable move-in-ready residence, or the property can be redeveloped to suit the buyer's vision. Ideal for end-users, builders, or investors seeking a prime lot with long-term upside. Surrounded by custom homes and mature landscaping, with easy access to top-rated schools, Bayview amenities, York Mills, and major transit routes. Opportunities to secure large ravine lots in this neighbourhood are extremely limited. Property being sold as is, where is. No representations or warranties.
31 Bearwood Drive, Toronto
5
BEDS
6
BATHS
$2,998,000
FOR SALE
Welcome to stunning home in the prestigious Edenbridge-Humber Valley neighbourhood. Set on a rare, whisper-quiet lot, this thoughtfully renovated 5-bedroom, 6-bathroom home offers an extraordinary blend of privacy, natural beauty, and refined design, with serene, picturesque views throughout. The interior is highlighted by an oversized contemporary skylight that fills the home with abundant natural light. The chef-inspired kitchen features custom cabinetry, stone countertops, and appliances, seamlessly flowing into open-concept living, family, and dining spaces-perfectly designed for grand-scale entertaining. Experience modern sophistication with extensive pot lighting, expansive windows, and a bright walk-out lower level that opens to a beautifully landscaped outdoor oasis. Ideally located just steps from Lambton Golf & Country Club, James Gardens, and the Humber River trails, with convenient access to tennis clubs, shopping, and top-rated schools. Complete with a two-car garage and Tesla charging station, this home perfectly balances lifestyle, luxury, and location.
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