Rosedale-Moore Park Homes with 100+ Approx Age

Rosedale-Moore Park Homes with 100+ Approx Age

Welcome to Rosedale-Moore Park, one of Toronto's most cherished neighborhoods, where historic charm meets modern living. Nestled in the heart of the city, this vibrant community boasts a rich tapestry of tree-lined streets, stunning architecture, and a welcoming atmosphere that captures the essence of urban life.

Rosedale-Moore Park is renowned for its exquisite homes, many of which date back over a century. These residences showcase a variety of architectural styles, from elegant Victorian mansions to charming Tudor and Arts and Crafts homes. The character and history of these properties offer a unique opportunity for those seeking a home with a story to tell. Living in a house with 100+ years of history means you’re not just purchasing a residence; you’re becoming a part of a legacy that has stood the test of time.

The neighborhood is not only about beautiful homes; it also offers an array of amenities that cater to residents' needs. Enjoy leisurely strolls in the lush parks, such as Rosedale Park and Moore Park Ravine, where nature intertwines with the urban landscape. Families appreciate the proximity to top-rated schools, while foodies will delight in the diverse culinary scene, featuring everything from cozy cafes to upscale dining.

Rosedale-Moore Park is a neighborhood that embraces community spirit, with local events and gatherings fostering connections among neighbors. Whether you’re drawn to the historic homes or the vibrant lifestyle, this enchanting area offers something for everyone. Come discover the charm of Rosedale-Moore Park, where history and community unite to create an unparalleled living experience in Toronto.

Newest Rosedale-Moore Park Homes with 100+ Approx Age

114 Glen Road, Toronto
$9,880,000
8 Beds ⋅ 8 Baths ⋅ C13864318 MLS
Nestled in Toronto's prestigious Rosedale neighbourhood, this landmark mansion occupies an expansive 100' x 122' estate-sized lot and offers over 7,500 square feet of impeccably designed living spaces. With 7 + 1 generously proportioned bedrooms, 8 bathrooms, and an exceptional third-floor loft, this grand residence seamlessly blends historic architecture with the scale, elegance, and functionality. Originally built circa 1900 for the distinguished Applegath family, the home has been meticulously restored and thoughtfully maintained to preserve it's architectural heritage including a self portrait stain glass window of Mrs. Applegath herself. Drawing inspiration from the classical traditions of Italian Renaissance architect Andrea Palladiio - most notably his iconic Villa Rotunda in Vicenza, Italy - the home reflects timeless design and exceptional craftmanship. A majestic octagonal central hall, framed by twelve lonic columns, creates an unforgettable first impression and sets the tone for the rest of the residence. Throughout the home, rich period details abound: original oak hardwood floors, finely hand-craved oak mouldings and wainscoting, intricate millwork, and 6 fireplaces with decorative tile and brick hearths. The soaring 10-foot ceilings are adorned with ornate plaster crown mouldings, ceiling medallions, and oak-beamed details that speak to the home's historical significance. Expansive bow windows and beautifully preserved stained glass flood the interior with natural light and highlight the warm, elegant atmosphere. Outside, the property is a private oasis, surrounded by mature trees, lush landscaping, and tranquil gardens that offer rare serenity in the heart of the city. A detached two-car garage and additional parking for three vehicles provide added convenience. This is a once-in-a-generation opportunity to own a truly iconic Rosedale residence - an architectural treasure steeped in history and timeles

114 Glen Road, Toronto
105 Clifton Road, Toronto
$1,799,000
4 Beds ⋅ 4 Baths ⋅ C13861980 MLS
A rare opportunity in prime Moore Park! Set on a quiet, tree-lined street, 105 Clifton Road offers the space, character and flexibility to bring your vision to life. Discover a home with plenty of warmth and character to build upon, including solid oak hardwood floors, crown mouldings, cedar-lined closets and a wood-burning fireplace with brick surround. A bright, generous family room with skylights opens directly to the rear deck and garden, while a detached garage adds everyday convenience. Upstairs, an extraordinarily rare five-room layout offers four formal bedrooms plus a dedicated tandem office/nursery - giving a growing family the flexibility for work, guests, hobbies or whatever comes next. A main-floor powder room and separate side entrance to the lower level add even more versatility, with a rec room, servery and bath already in place. Walk to dining and shops along Yonge and St. Clair, subway transit, and the serene trails of the Moore Park Ravine--with the best of Midtown close at hand. Bring your ideas, bring your vision, and make 105 Clifton Road the home you've always imagined.

105 Clifton Road, Toronto
106 Highland Avenue, Toronto
$3,750,000
5 Beds ⋅ 5 Baths ⋅ C13818260 MLS
There's a certain kind of house that feels made for family life, and 106 Highland Avenue is exactly that. Set well back from the street on an exceptional 39' x 150' lot in prime North Rosedale, this handsome red-brick semi offers privacy, space and permanence. Approximately 4,000 sf (total). Completely renovated in 2015 by architect Peter Higgins, it pairs remarkable craftsmanship with thoughtful, enduring design. Step into the foyer, where heated floors & a fluted wood feature wall offer the first glimpse of the detail found throughout. The main floor features a chef's kitchen with Wolf & Miele appliances and generous island seating, opening to a large dining area. Beyond, the family room overlooks the expansive rear garden, while the elegant living room features a gas fireplace & stone mantel. Upstairs, the private primary suite offers 2 walk-in closets, its own gas fireplace, & a beautifully appointed ensuite with deep soaker tub. A 2nd spacious bedroom includes a 4-piece ensuite & walk-in closet. The 3rd floor features 2 oversized, light-filled bedrooms with custom built-ins, a shared 3-piece bath and an additional laundry room. The L/L is exceptionally functional, with high ceilings & a walkout. A heated-floor mudroom provides plenty of storage, while the expansive rec room offers space to play & work, including a dedicated office area. An additional bedroom or gym, 3-piece bath & laundry room complete the level. Outside, the rear garden is beautifully centred around an elegant fountain, creating a tranquil setting for entertaining. A long private driveway & the home's generous setback create an added sense of privacy, while a covered side storage area keeps bikes, & all the equipment of family life neatly out of the way. Walk to Summerhill Market for Saturday-morning groceries, wander the nearby ravine trails, & enjoy close proximity to Branksome Hall & Whitney Junior P.S.- all while coming home to a quiet, established North Rosedale street.

106 Highland Avenue, Toronto
32 Edgewood Crescent, Toronto
$2,649,000
5 Beds ⋅ 3 Baths ⋅ C13809074 MLS
ELEGANT EDGEWOOD Beautifully renovated and completely turnkey, this elegant North Rosedale home is tucked away on one of the neighbourhood's most coveted cul-de-sacs - a quiet, private setting with a wonderful sense of community. The main floor is bright with an open-concept layout designed for both everyday living and effortless entertaining.Upstairs, the spacious primary suite is a serene retreat, complemented by a spa-inspired bathroom and freestanding tub. The generous second bedroom offers plenty of space and flexibility for a guest room, home office or growing family. The light-filled third floor adds another layer of living space, equally suited to a children's retreat, playroom, study or relaxed family room. It's the kind of flexible space that evolves with the needs of a family. Outside, the private, low-maintenance backyard feels like a natural extension of the home. There's ample space for outdoor dining, summer entertaining and laid back afternoons, with a gas line already in place for the BBQ. Set in one of Toronto's most established and sought-after neighbourhoods, the home is moments from amazing parks, exceptional schools and the everyday conveniences of the city, including highly regarded Whitney Public School. A refined, thoughtfully renovated home in an exceptionally special North Rosedale setting.

32 Edgewood Crescent, Toronto
37 St Andrews Gardens, Toronto
$5,600,000
6 Beds ⋅ 5 Baths ⋅ C13799918 MLS
Newly renovated from top to bottom, this stately five-bedroom residence is set on one of North Rosedale's most private and established streets, offering the very best of Rosedale living-refined, timeless & beautifully appointed throughout. The main level features luxurious herringbone floors. A timeless kitchen, anchored by a Wolf range & expansive centre island, flows seamlessly into the adjoining family room. Both spaces open to the rear yard & deck through wall-to-wall picture windows, while a gas fireplace warms the heart of the home. A formal dining room suits family gatherings, while a versatile living room-with its own gas fireplace-works equally well as an elegant sitting room, home office or piano room. A side entrance from the driveway adds everyday convenience. Upstairs, the generous primary suite features a sizeable walk-in closet & completely reimagined five-piece ensuite with sophisticated finishes. French doors open to a south-facing balcony overlooking the rear yard. Two well-proportioned secondary bedrooms, a four-piece family bathroom & brand-new hardwood floors complete the second level. The third floor offers two additional bedrooms: a spacious room with a walk-in closet & private south-facing balcony overlooking the treetops, plus a second ideally suited to children or guests. An additional four-piece bathroom completes this level. Heated floors extend throughout the lower level, featuring a sizeable recreation room with gas fireplace, dedicated gym enclosed by a full glass partition wall, sixth bedroom & three-piece bathroom with curbless shower. Outside, a resort-style backyard awaits, with a concrete pool & integrated hot tub, cabana with cedar sauna, pergola & multiple seating areas creating a private oasis for effortless al fresco entertaining. Steps from Chorley & Rosedale Park, the boutique shops of Summerhill Avenue, this newly transformed residence presents a rare opportunity to secure one of North Rosedale's most coveted addresses.

37 St Andrews Gardens, Toronto
78 Crescent Road Unit 2, Toronto
$5,295,000
3 Beds ⋅ 3 Baths ⋅ C13792396 MLS
A remarkable opportunity to live in this prime Rosedale location in a space that has been transformed into total perfection. This editorial worthy masterpiece is approx 3,500 sf of bright living space. The grand great room (originally a ballroom) will become the focus of your life with the impressive stone wood-burning fireplace and decorative plaster ceiling. Perfect for entertaining and flows out to the large picturesque terrace. The bright family-sized kitchen is stunning with top-of-the-line appliances and finishes. Relax in the family room with a gas fireplace and custom millwork. Spacious primary suite with walk-in closet and attached dressing room and office, and stunning 5-piece spa-like ensuite. There are multiple walk-outs to a sublime terrace overlooking the trees of Rosedale and the skyline beyond. The lower level has a great multiple purpose room (currently used as a gym) and bedroom with ensuite. The deep history of this Rosedale mansion, which once housed Sir Henry Pellatt (of Casa Loma), can be felt throughout with timeless details and points of interest. Intricate moulding details, arched doorways, stone wood-burning fireplace, and a spectacular grand staircase with a showpiece chandelier. Three car parking: [two surface parking spaces at front of house plus one garage parking]. The location cannot be beat. Walk to Yonge St amenities, Subway, and green spaces. This magnificent, unique, and stylish home is perfect for those looking for modern living in the coveted Rosedale neighbourhood.

78 Crescent Road Unit 2, Toronto
43 Whitehall Road, Toronto
$3,999,000
4 Beds ⋅ 4 Baths ⋅ C13787722 MLS
Tucked along one of Rosedale's most coveted streets, 43 Whitehall Road is a rare offering: an impeccably finished residence with the pedigree of the neighbourhood and the flexibility today's most discerning buyers are looking for. Beyond the classic façade, over 3,000 square feet of beautifully appointed living unfolds across two finished levels - four bedrooms, four bathrooms, and interiors finished to an exacting standard, where timeless architecture meets a considered, modern sensibility. What truly sets this home apart is what comes next. A fully permitted and roughed-in third floor and basement add an additional 1800 square feet - waiting for the next owner's own touches. It's a rare canvas: the freedom to enjoy the home as it is, a grand single-family residence, or to thoughtfully introduce income potential. The vision is approved; the possibilities are yours. All told, that's over 4,500 square feet of potential on one of Toronto's most distinguished streets - impeccably finished today, and ready to become entirely your own. And the location is second to none. Enjoy a quick stroll to the shops and cafés of Summerhill, and settle into one of the city's most sought-after school catchments - served by top-rated public and private schools including Whitney Junior Public School, Our Lady of Perpetual Help, and Branksome Hall. This is Rosedale living with room to dream - a distinguished address, exquisitely finished, and ready for its next chapter.

43 Whitehall Road, Toronto
43 Maple Avenue, Toronto
$5,495,000
6 Beds ⋅ 5 Baths ⋅ C13753998 MLS
Set discreetly behind a wall of mature hedges, this grand Rosedale residence occupies a remarkable bright corner lot, its width and setting allowing for a scale and presence rarely found. Manicured front gardens feel like the pages of a magazine and introduce a home where beautiful proportions, original character and thoughtful renovation come together effortlessly. The expansive main floor retains the elegance of formal living and dining rooms + a grand foyer, while a renovated kitchen opens to a generous family room with coffered ceilings and oversized character windows. A private office like a sun room and substantial mudroom with exceptional floor-to-ceiling storage and a separate side entrance offering a natural connection to the lower level nanny suite. The completely reconfigured and beautifully renovated second floor is devoted to two impressive bedroom suites. The primary is particularly exceptional, with a beautifully scaled ensuite and steam shower and dream walk-in closet. Two additional bedrooms occupy the third floor alongside a second laundry area, and a relaxed family room, an ideal space for children, guests or potential fifth bedroom. Outside, the property becomes its own private world. Lush gardens surround a saltwater pool with waterfall, outdoor kitchen, stone terrace and covered, heated pergola with outdoor fireplace and television, creating a backyard designed to be lived in from spring through fall. A private driveway accommodates 2+ cars, while the garage offers parking for up to 3 with the existing lift. Generous in proportion yet remarkably private, this is a Rosedale home of exceptional space and presence, both inside and out.

43 Maple Avenue, Toronto
80 Binscarth Road, Toronto
$5,795,000
5 Beds ⋅ 5 Baths ⋅ C13422080 MLS
Set along one of Rosedale's most established and private streets, 80 Binscarth Rd offers a rare combination of timeless architecture, contemporary refinement and exceptional family functionality. Set on a deep 31 x 150 ft lot within one of Rosedale's most coveted and tightly held pockets, this detached 4+1 bedroom,5 bathroom residence pairs timeless architecture with calm, contemporary interiors. Defined by quiet tree-lined streets, landmark homes, privacy and enduring long-term value, this exceptional enclave is among the finest in the neighbourhood. The home has been meticulously maintained and extensively renovated over the years with significant investment and a careful commitment to preserving its timeless Rosedale character. A refined Bulthaup kitchen with Gaggenau appliances anchors the main floor, complemented by pale oak floors, custom millwork, both gas and wood-burning fireplaces and oversized windows that flood the interiors with natural light. Formal principal rooms balance warmth and sophistication while offering seamless functionality for family living and entertaining. Upstairs, four spacious bedrooms include a serene primary retreat with a generous dressing room/walk-in closet, garden views and a beautifully updated ensuite. Secondary bathrooms have also been thoughtfully renovated with timeless finishes and exceptional attention to detail. The lower level offers excellent flexibility with a recreation/media space, gym area, additional bedroom or office, full bathroom, laundry and extensive storage. Outdoor spaces feel private and immersive, with mature landscaping, layered gardens and multiple seating areas creating a true urban retreat. A rare offering that combines architectural integrity, exceptional livability, and one of the most prestigious residential settings in Toronto.

80 Binscarth Road, Toronto
82 Chestnut Park Road, Toronto
$12,500,000
5 Beds ⋅ 6 Baths ⋅ C13227720 MLS
Extremely rare endless summer escape in a poolside paradise with 7-Star resort-style luxury! Experience the ultimate retreat in the most sought-after and prestigious Rosedale neighborhood, west of Mt. Pleasant. Embraced by mature trees and manicured lawns, this extraordinarily expansive 85-foot-wide tableland property sits atop the exclusive Chestnut Park ravine, overlooking serene parkland below and feels like a private country estate. A true garden oasis, the stunning oversized pool is virtually irreplaceable in this area, creating an idyllic opportunity for captivating family living and exceptional entertaining. Spanning nearly 8,000 square feet, this elegant Georgian residence is in a picture-perfect position on this magically lamp-lit street just 2 blocks from Yonge. The garden features sprawling multiple terraces for sitting, dining, and entertaining, complete with an outdoor kitchen. Inside, discover gracefully curated interiors & a truly sumptuous sky-lit primary suite with lush treetop views, a sitting area with fireplace, his & her separate dressing rooms and spa-inspired ensuite. This sleek trophy property blends transitional modernity, alluring charm & unparalleled privacy with modern convenience and spectacular luxury in a truly prized neighborhood. Additional highlights include an ELEVATOR, generator, garage with lift & ensuite bathrooms in all bedrooms for superb flexibility. Set beneath a treed canopy for total privacy, you are just steps from the subway, excellent private & public schools, premier shopping, area parks, tennis, skating & hiking & biking trails extending to the lake with Yorkville & the city center only a 10-minute drive away. For those who value permanence, treasured memories will resonate for all in this enduring and stable investment!

82 Chestnut Park Road, Toronto
41 Nanton Avenue, Toronto
$4,650,000
4 Beds ⋅ 3 Baths ⋅ C13135368 MLS
Visit REALTOR website for additional information. Exquisite Georgian Revival Residence on Coveted Nanton Avenue, Rosedale Seldom does an opportunity of this magnitude present itself.Situated on one of Rosedale's most prestigiousstreets,this grand three-storey Georgian Revival residence occupies a rare 50x150-foot lot,offering exceptional privacy and expansive outdoor living.Designed by renowned architectBeaumont Jarvis as his own personal residence, the home is rich in history,elegance,andarchitecturalsignificance. Its timeless beauty has also attracted Hollywood attention,havingbeen featured in acclaimed television productions including Suits and 12Monkeys.Thedistinctive Dutch Gambrel roof and stately façade create an unforgettable first impression.Inside,the home has been meticulously restored to preserve its original charm whileincorporating modern luxury.Extraordinary period details include soaring 4x16-foot beams,leaded and stained-glass windows,intricate mouldings,and grand principal rooms designed forelegant entertaining and comfortable family living.A chef-inspired kitchen features aFrench-imported Lacanche range and premium Gaggenau refrigeration.Two staircases connect the thoughtfully designed three levels, balancing sophistication withpracticality. The rear mudroom opens to breathtaking mature gardens and an oversized backyardoasis with private garage,perfect for entertaining, alfresco dining,or even a private skatingrink beneath the stars in winter.Offering four spacious bedrooms and three beautifully appointed bathrooms,the home provides abundant natural light and refined comfort throughout.One of Toronto's original poured concrete homes,it boasts remarkable durability and structuralintegrity rarely found today.Located steps from the subway, this exceptional residence combinesserene luxury with effortless downtown Toronto access.Surrounded by top-tier schools and acelebrated family-friendly community,this is a rare opportunity to own a landmark property

41 Nanton Avenue, Toronto
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