High Park-Swansea Homes with 100+ Approx Age

High Park-Swansea Homes with 100+ Approx Age

Welcome to High Park-Swansea, one of Toronto's most enchanting neighborhoods, where the charm of historic homes meets the vibrancy of urban life. Nestled along the picturesque shores of Lake Ontario, this area boasts a rich tapestry of culture, nature, and community spirit that captivates residents and visitors alike.

High Park-Swansea is renowned for its stunning natural beauty, highlighted by the expansive High Park—a sprawling green oasis featuring lush gardens, serene walking trails, and a beautiful lakefront. This beloved park is perfect for family picnics, leisurely strolls, and outdoor activities, making it a cherished retreat for locals.

The neighborhood is characterized by its unique blend of architectural styles, with many homes boasting an impressive age of over 100 years. These charming residences reflect the craftsmanship of a bygone era, showcasing intricate details and timeless designs that tell the story of the neighborhood's rich history. From stately Victorian houses to quaint bungalows, each home exudes character and warmth, providing a perfect backdrop for family life.

High Park-Swansea is also a community that thrives on connection. With a strong sense of belonging, residents enjoy a variety of local amenities, including cozy cafes, boutique shops, and vibrant restaurants. The area is well-served by public transportation, making it easy to access downtown Toronto while still enjoying the tranquility of suburban living.

Whether you're drawn to the historic homes, the lush landscapes, or the welcoming community vibe, High Park-Swansea offers an idyllic setting for those seeking a harmonious blend of nature and urban convenience. Come explore this beautiful neighborhood and discover the charm that awaits!

Newest High Park-Swansea Homes with 100+ Approx Age

$1,790,000
3 Beds ⋅ 2 Baths ⋅ W13571624 MLS
Two-floor executive penthouse in the Abbey, an iconic church conversion. Open concept luxury with 10m ceilings, wall to wall custom-built upgrades. Cherry floors & cabinetry, Artimede lights, exposed beams, original windows, limestone walls. The best suite in the building. Perfectly situated for High Park, Lake, Roncey Village, Bloor West, Libraries, Schools, Hospital, TTC, Restuarants. This area has it all.

384 Sunnyside Avenue Unit 308, Toronto
$2,980,000
10 Beds ⋅ 8 Baths ⋅ W13565680 MLS
Exceptional investment opportunity! Legal detached 4-plex plus a legal non-conforming basement apartment offering over 6,700 sq. ft. of living space in the heart of High Park. Fully tenanted with separate hydro meters and an outstanding tenant community. Each unit features its own private walkout deck overlooking mature greenery. Lifetime slate roof, two private driveways (Indian Rd. & Howard Park Ave.), legal parking for 3 with space for 10+ vehicles. Minutes to High Park, Sunnyside Beach, the Martin Goodman Trail, Bloor West Village, TTC, and major highways. Ideal for investors, owner-occupiers, or future single-family conversion. **FLOOR PLANS AVAILABLE**

244 Indian Road, Toronto
$899,999
3 Beds ⋅ 1 Baths ⋅ W13547838 MLS
Rare Opportunity in Toronto's Desirable High Park Swansea. Welcome to 269 Windermere Avenue, a detached home, offered for the first time in years, this property is a blank canvas awaiting your vision. Situated on a desirable lot in a mature, tree-lined neighbourhood, this is your chance to invest in one of Toronto's most sought-after communities. Just minutes from the Iconic High Park, residents have access to over 400 acres of green space featuring walking and cycling trails, sports facilities, playgrounds, a zoo, beautiful gardens, and year-round community events. Spend weekends exploring nature, enjoying a picnic, or taking in the famous cherry blossoms each spring. Take in Bloor West Village, The Junction, and Roncesvalles Village and enjoy easy access to boutique shopping, cafés, restaurants, parks, recreation centres, highly rated schools, and everyday conveniences. Excellent TTC service, nearby subway stations, GO Transit, and quick access to major highways make commuting throughout the city effortless. A truly exceptional opportunity for renovators, builders, investors, or families looking to create a custom home in an outstanding location. Don't miss your chance to unlock the potential of this classic Toronto property.

269 Windermere Avenue, Toronto
$2,199,000
6 Beds ⋅ 4 Baths ⋅ W13509134 MLS
Offered for the first time in two generations, a truly exceptional residence that presents a rare opportunity to acquire one of the neighbourhood's distinguished legacy properties. Occupying a prominent 27 x 126.81ft corner lot, this stately home seamlessly blends historic charm with remarkable versatility, offering endless possibilities for families, investors, builders, and those seeking a multigenerational residence in one of Toronto's most coveted communities.Encompassing 3,490 of total living space, the home welcomes you through a gracious vestibule that sets the tone for the impressive scale and timeless character. Generous principal rooms, abundant natural light, and enduring architectural details create an inviting atmosphere while providing the perfect canvas for restoration, modernization, or reimagining.Configured as a well-maintained income-producing property, the residence is occupied by exceptional tenants. The property offers outstanding flexibility with five separate hydro meters, a dedicated coin-operated laundry facility, and private balconies serving each of the above-grade suites-features that enhance both tenant appeal and long-term investment value. Modern mechanical upgrades include a tankless hot water system, providing efficient, on-demand hot water.Outside, the property's scale is equally impressive. A rare detached three-car garage complemented by parking for eight vehicles is virtually unheard of in this prestigious neighbourhood, creating unmatched convenience for homeowners, extended families, or investment use. The expansive corner lot further presents exciting opportunities for future enhancement or redevelopment and is garden suite eligible.Properties of this significance seldom become available. Rich in history, exceptional in scale, and brimming with future potential, 376 Sunnyside Avenue represents a once-in-a-generation opportunity to own a remarkable family legacy while creating the next chapter of its enduring story.

376 Sunnyside Avenue, Toronto
$4,988,000
5 Beds ⋅ 4 Baths ⋅ W13233364 MLS
A spectacular and seldom-offered ravine property, 187 Ellis Avenue presents a once-in-a-generation opportunity to own one of Toronto's most coveted and private parcels of land. Located on the shores of Grenadier Pond with sweeping views of High Park's ancient canopy, this extraordinary property offers the rare sensation of a wooded countryside retreat - mere minutes from the very heart of the city.The exceptional lot spans 70 feet in width and an impressive 512.5 feet in depth, encompassing 0.82 acres of lush ravine land. Whether envisioned as the site of a masterfully designed bespoke residence or a lovingly restored character home, the potential here is unparalleled.The existing home unfolds across three levels totalling 4,215 square feet, offering four generously proportioned bedrooms and three-and-a-half bathrooms. A two-car garage with attached workshop adds exceptional utility, complemented by two additional driveway spaces. The ravine setting ensures a degree of seclusion rarely achieved on a Toronto residential lot, with mature trees providing a natural privacy screen.Situated in the prestigious Swansea neighbourhood, this address places residents within walking distance of the Bloor West Village's celebrated shops and restaurants and top-rated schools including Swansea PS and Humberside Collegiate. Convenient access to the Gardiner and Bloor subway line ensures effortless connectivity to downtown, the airport and beyond. Renovate to your exacting standards or build the residence you have always envisioned. Properties of this magnitude, in this location, simply do not come to market. 187 Ellis Avenue is not merely a listing - it is a legacy.

187 Ellis Avenue, Toronto
$3,699,000
6 Beds ⋅ 4 Baths ⋅ W13222646 MLS
Just Right on Wright! Set on one of Roncesvalles' most loved streets, this 6 bedroom, 4 bathroom detached home blends architectural scale with historical warmth that is truly unmatched. Renovated with prestigious, award winning design team Two Fold Interiors in 2023, the interior pairs clean lines, natural textures, and carefully chosen finishes to create spaces that feel both refined and family friendly. The kitchen anchors the home with custom millwork, generous proportions, and an easy connection to the surrounding living spaces, making it equally suited to everyday family life and entertaining. If you're looking for a home that feels open but not cavernous - this is it! A whopping 3850sqft of living space spanning 4 levels, the layout offers incredible flexibility for growing families, guests, and work from home living. Find the primary suite on the 2nd floor with 2 office spaces/bedrooms. The 3rd floor features 3 more bedrooms providing both function and privacy while maintaining a cohesive feel throughout the home. The lower level features a rec room and separate kitchen/wet bar so everyone has a space to hang. Outside, the property offers a massive 22x20' deck and double garage. Turn west and you're one block from the largest park in Toronto and kilometers of hiking trails (the 'hood's best off-leash dog walk) or turn east and head to Roncesvalles for shopping and award winning restaurants! You've got all the best energy of the west end at your fingertips!! A stunning family home in one of Toronto's most loved neighbourhoods!

286 Wright Avenue, Toronto
$3,295,000
7 Beds ⋅ 4 Baths ⋅ W13081566 MLS
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.

51 Indian Grove, Toronto
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