135 MADISON AVENUE - Photo 1 of 50, Toronto (Annex), Ontario
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$3,995,000

135 MADISON AVENUE — Toronto (Annex), Ontario

M5R2S3

6Beds
5Baths
2Parking

About This Property

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, wainscotting, 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 2 large bedrooms on the second floor as well as 2 full washrooms, a dedicated laundry room, and a large sunny deck. The third floor would make a fabulous primary suite and currently includes a large living room, kitchen, two additional bedrooms and a large deck with skyline and treetop views. The basement is partially finished with 7 foot ceilings and features a separate entrance. This home has been used as single family for many years but has potential for many 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. Great opportunity for those looking for a co-ownership property! (id:63357)

Property Details

Property Type
Detached
Bedrooms
6
Bathrooms
5
Stories
3.0
Status
Active

Location & Neighborhood

What's nearby 135 MADISON AVENUE

Lifestyle Summary

** Living at 135 Madison Avenue means embracing a dynamic and fulfilling lifestyle in one of Toronto’s most beloved neighborhoods. With its rich cultural offerings, convenient transit options, and a strong sense of community, the Annex provides the perfect blend of urban excitement and suburban comfort. Residents can enjoy local amenities, diverse dining experiences, and a plethora of recreational opportunities, making every day feel like a new adventure. Whether you’re a young professional, a growing family, or anyone in between, the Annex welcomes you to call it home.

🏘️Neighborhood Vibe

** The Annex is a vibrant and eclectic neighborhood known for its artistic flair and historic architecture. Tree-lined streets are filled with a mix of charming boutiques, bookstores, and cafes, creating a warm and welcoming atmosphere that invites residents to explore and connect. With a diverse community and a blend of cultures, the Annex embodies a lively urban lifestyle while retaining a sense of intimacy. **COMMUTER_SUMMARY:** Commuting from 135 Madison Avenue is a breeze, thanks to the proximity to multiple transit options. With several bus stops just a short walk away and the Spadina Road subway station nearby, residents can easily navigate downtown Toronto and beyond. This accessibility makes it convenient for professionals and families alike to reach their destinations with ease. **FAMILY_SUMMARY:** Families will appreciate the excellent educational options available in the area, with several well-regarded schools such as Huron Street Junior Public School and Taddle Creek Montessori just a stone's throw away. The neighborhood's family-friendly parks and playgrounds provide ample opportunities for outdoor play and community engagement. With a nurturing environment, the Annex is an ideal place for children to grow and thrive. **DINING_ENTERTAINMENT:** Food lovers will feel right at home in the Annex, with a delightful array of dining options just around the corner. From cozy cafes like Ezra's Pound and Wey Cup to mouthwatering restaurants such as Casa Mezcal and The Backyard Smokehouse, there’s something to satisfy every palate. Whether you're seeking a casual brunch or a vibrant dinner, this neighborhood promises a culinary adventure. **OUTDOOR_RECREATION:** Nature enthusiasts will find plenty to enjoy in the Annex, with several parks and green spaces nearby. Jean Sibelius Square and Taddle Creek Park offer serene spots for picnics, leisurely strolls, or family gatherings. The area's parks are perfect for active lifestyles, providing playgrounds and open spaces for children and adults alike to unwind and appreciate the outdoors. **OVERALL_LIFESTYLE:** Living at 135 Madison Avenue means embracing a dynamic and fulfilling lifestyle in one of Toronto’s most beloved neighborhoods. With its rich cultural offerings, convenient transit options, and a strong sense of community, the Annex provides the perfect blend of urban excitement and suburban comfort. Residents can enjoy local amenities, diverse dining experiences, and a plethora of recreational opportunities, making every day feel like a new adventure. Whether you’re a young professional, a growing family, or anyone in between, the Annex welcomes you to call it home.

🚗Commuting

** Commuting from 135 Madison Avenue is a breeze, thanks to the proximity to multiple transit options. With several bus stops just a short walk away and the Spadina Road subway station nearby, residents can easily navigate downtown Toronto and beyond. This accessibility makes it convenient for professionals and families alike to reach their destinations with ease. **FAMILY_SUMMARY:** Families will appreciate the excellent educational options available in the area, with several well-regarded schools such as Huron Street Junior Public School and Taddle Creek Montessori just a stone's throw away. The neighborhood's family-friendly parks and playgrounds provide ample opportunities for outdoor play and community engagement. With a nurturing environment, the Annex is an ideal place for children to grow and thrive. **DINING_ENTERTAINMENT:** Food lovers will feel right at home in the Annex, with a delightful array of dining options just around the corner. From cozy cafes like Ezra's Pound and Wey Cup to mouthwatering restaurants such as Casa Mezcal and The Backyard Smokehouse, there’s something to satisfy every palate. Whether you're seeking a casual brunch or a vibrant dinner, this neighborhood promises a culinary adventure. **OUTDOOR_RECREATION:** Nature enthusiasts will find plenty to enjoy in the Annex, with several parks and green spaces nearby. Jean Sibelius Square and Taddle Creek Park offer serene spots for picnics, leisurely strolls, or family gatherings. The area's parks are perfect for active lifestyles, providing playgrounds and open spaces for children and adults alike to unwind and appreciate the outdoors. **OVERALL_LIFESTYLE:** Living at 135 Madison Avenue means embracing a dynamic and fulfilling lifestyle in one of Toronto’s most beloved neighborhoods. With its rich cultural offerings, convenient transit options, and a strong sense of community, the Annex provides the perfect blend of urban excitement and suburban comfort. Residents can enjoy local amenities, diverse dining experiences, and a plethora of recreational opportunities, making every day feel like a new adventure. Whether you’re a young professional, a growing family, or anyone in between, the Annex welcomes you to call it home.

👨‍👩‍👧‍👦Family Living

** Families will appreciate the excellent educational options available in the area, with several well-regarded schools such as Huron Street Junior Public School and Taddle Creek Montessori just a stone's throw away. The neighborhood's family-friendly parks and playgrounds provide ample opportunities for outdoor play and community engagement. With a nurturing environment, the Annex is an ideal place for children to grow and thrive. **DINING_ENTERTAINMENT:** Food lovers will feel right at home in the Annex, with a delightful array of dining options just around the corner. From cozy cafes like Ezra's Pound and Wey Cup to mouthwatering restaurants such as Casa Mezcal and The Backyard Smokehouse, there’s something to satisfy every palate. Whether you're seeking a casual brunch or a vibrant dinner, this neighborhood promises a culinary adventure. **OUTDOOR_RECREATION:** Nature enthusiasts will find plenty to enjoy in the Annex, with several parks and green spaces nearby. Jean Sibelius Square and Taddle Creek Park offer serene spots for picnics, leisurely strolls, or family gatherings. The area's parks are perfect for active lifestyles, providing playgrounds and open spaces for children and adults alike to unwind and appreciate the outdoors. **OVERALL_LIFESTYLE:** Living at 135 Madison Avenue means embracing a dynamic and fulfilling lifestyle in one of Toronto’s most beloved neighborhoods. With its rich cultural offerings, convenient transit options, and a strong sense of community, the Annex provides the perfect blend of urban excitement and suburban comfort. Residents can enjoy local amenities, diverse dining experiences, and a plethora of recreational opportunities, making every day feel like a new adventure. Whether you’re a young professional, a growing family, or anyone in between, the Annex welcomes you to call it home.

🍽️Dining & Entertainment

** Food lovers will feel right at home in the Annex, with a delightful array of dining options just around the corner. From cozy cafes like Ezra's Pound and Wey Cup to mouthwatering restaurants such as Casa Mezcal and The Backyard Smokehouse, there’s something to satisfy every palate. Whether you're seeking a casual brunch or a vibrant dinner, this neighborhood promises a culinary adventure. **OUTDOOR_RECREATION:** Nature enthusiasts will find plenty to enjoy in the Annex, with several parks and green spaces nearby. Jean Sibelius Square and Taddle Creek Park offer serene spots for picnics, leisurely strolls, or family gatherings. The area's parks are perfect for active lifestyles, providing playgrounds and open spaces for children and adults alike to unwind and appreciate the outdoors. **OVERALL_LIFESTYLE:** Living at 135 Madison Avenue means embracing a dynamic and fulfilling lifestyle in one of Toronto’s most beloved neighborhoods. With its rich cultural offerings, convenient transit options, and a strong sense of community, the Annex provides the perfect blend of urban excitement and suburban comfort. Residents can enjoy local amenities, diverse dining experiences, and a plethora of recreational opportunities, making every day feel like a new adventure. Whether you’re a young professional, a growing family, or anyone in between, the Annex welcomes you to call it home.

🌳Outdoor Recreation

** Nature enthusiasts will find plenty to enjoy in the Annex, with several parks and green spaces nearby. Jean Sibelius Square and Taddle Creek Park offer serene spots for picnics, leisurely strolls, or family gatherings. The area's parks are perfect for active lifestyles, providing playgrounds and open spaces for children and adults alike to unwind and appreciate the outdoors. **OVERALL_LIFESTYLE:** Living at 135 Madison Avenue means embracing a dynamic and fulfilling lifestyle in one of Toronto’s most beloved neighborhoods. With its rich cultural offerings, convenient transit options, and a strong sense of community, the Annex provides the perfect blend of urban excitement and suburban comfort. Residents can enjoy local amenities, diverse dining experiences, and a plethora of recreational opportunities, making every day feel like a new adventure. Whether you’re a young professional, a growing family, or anyone in between, the Annex welcomes you to call it home.

Parks & Recreation

Transit Access

Local Amenities

Coffee & Cafes

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Last updated: Jan 28, 2026

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$3,995,000