Rosedale is a highly sought-after neighbourhood in Toronto, known for its stately mansions, tree-lined streets, and lush parks. Situated in midtown Toronto, Rosedale is home to some of the city's most affluent residents, as well as a mix of boutique shops, high-end restaurants, and cultural attractions. The neighbourhood is also home to some of Toronto's most prestigious private schools, making it a popular choice for families with children. Rosedale is bordered by the scenic Rosedale Ravine, which offers residents and visitors alike a tranquil escape from the city's urban energy. Visitors to Rosedale can explore the neighbourhood's many parks, including Rosedale Park and Chorley Park, or take a stroll along the picturesque Beltline Trail. With its refined elegance and exclusive atmosphere, Rosedale is a coveted address in Toronto, offering residents a luxurious lifestyle in the heart of the city.
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Rosedale Listings
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104 Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C13824430
104 Park Road Toronto M4W 2N7 
$7,500,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13824430
- Bedrooms:
- 5
- Bathrooms:
- 5
Originally a stately classic residence, this exceptional Rosedale home was thoughtfully reimagined in 2021 under the direction of acclaimed interior designers Michelle R. Smith andHayley Bridget Cavagnolo. The result is a rare and seamless blend of timeless character and contemporary luxury-refined, welcoming, and rich in detail. Set behind lush landscaping, the home offers striking street presence with a quiet confidence that immediately captures attention. Inside, five bedrooms and five beautifully designed bathrooms are complemented by craftsmanship rarely found. Hand-painted flooring throughout the main level adds subtle artistry, while three wood-burning fireplaces-one anchoring the kitchen-bring warmth and charm to everyday living.The chef's kitchen is both functional and elegant, featuring a Wolf range, Sub-Zero Pro Series refrigeration, an oversized eat-in area, and a walk-out to an expansive deck that seamlessly extends the living space outdoors. A butler's pantry adds thoughtful storage and effortless entertaining appeal. Designed for hosting and relaxing alike, the home features a built-in Sonos sound system throughout the interior and backyard. Outdoors, a private resort-style setting awaits with a saltwater pool equipped with smart heating and lighting-perfect for year-round enjoyment.The third-floor retreat offers exceptional flexibility, complete with a family lounge, workspace, guest bedroom, full bath, and private rooftop deck. On the lower level, a sauna provides a spa-like escape, completing this truly one-of-a-kind Rosedale residence. More detailsListed by SAGE REAL ESTATE LIMITED- The Living TO Team
- Living TO
- (647)424-0453
- info@livingto.ca
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Main 31 Whitehall Road in Toronto: Rosedale-Moore Park House for lease (Toronto C09) : MLS®# C13825400
Main 31 Whitehall Road Toronto M4W 2C5
$3,995Residential Freehold- Status:
- For Lease
- MLS® Num:
- C13825400
- Bedrooms:
- 3
- Bathrooms:
- 1
Welcome to your dream home in the highly sought-after neighborhood of Rosedale! This stunning 3-bedroom unit is bathed in natural light and designed for both comfort and convenience. The spacious primary bedroom boasts a delightful walkout to an expansive deck, perfect for enjoying morning coffee or evening gatherings in total privacy. With a dedicated parking space included, you'll appreciate the ease of city living. A separate laundry adds to the practicality. Located just moments away from everything the city has to offer, this home provides the perfect blend of tranquility and quick commute options including 5 min drive to the DVP and a quick stroll to Rosedale Station and Summerhill Market. Don't miss the chance to make this exceptional property your own! More detailsListed by RE/MAX REALTRON BARRY COHEN HOMES INC.- The Living TO Team
- Living TO
- (647)424-0453
- info@livingto.ca
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105 Roxborough Street E in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C13820618
105 Roxborough Street E Toronto M4W 1V9
$5,495,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13820618
- Bedrooms:
- 6
- Bathrooms:
- 5
Welcome to 105 Roxborough Street East - a Grand Dame of South Rosedale and a rare opportunity to own one of the neighbourhood's magnificent early 1900s residences. Set on an exceptional 50' x 145' south-facing lot with sweeping city skyline views, this handsome red-brick home has the scale, presence & proportions of another era - and is absolutely flooded with sunlight throughout the day. From the moment you enter, the grandeur is undeniable. Soaring 10' ceilings on the main floor, 9' on the second & over 8' on the third. Incredible principal rooms. Beautiful original character. A gracious centre hall plan and the width that only a 50' lot can provide. Outside, a private drive leads to an unusually large 2-car garage at the rear - another Rosedale rarity. Move in & enjoy this wonderful home as it is, or reimagine it into an extraordinary residence for the next generation. The bones, scale, lot & location are all here.And the history! 105 Roxborough was once home to Lt.-Col. Arthur Godfrey Peuchen, prominent Toronto businessman, yachtsman & Titanic survivor, who crossed the Atlantic some 40 times and escaped the Titanic by climbing down a rope into Lifeboat No. 6. He spent his final days at this very address. All of this in one of South Rosedale's most coveted pockets - walk to Yonge Street, Rosedale subway, Branksome Hall, Rosedale Jr PS, shops, restaurants & neighbourhood favourites. A magnificent house with a fascinating past, incredible presence & an even more exciting future. This is the kind of Rosedale opportunity that simply cannot be recreated. More detailsListed by ROYAL LEPAGE REAL ESTATE SERVICES OXLEY REAL ESTAT- The Living TO Team
- Living TO
- (647)424-0453
- info@livingto.ca
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106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C13818260
106 Highland Avenue Toronto M4W 2A6 OPEN HOUSE: Sep 26, 202602:00 PM - 04:00 PM EDTOpen House on Saturday, September 26, 2026 2:00PM - 4:00PMOPEN HOUSE: Sep 27, 202602:00 PM - 04:00 PM EDTOpen House on Sunday, September 27, 2026 2:00PM - 4:00PM
$3,750,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13818260
- Bedrooms:
- 5
- Bathrooms:
- 5
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. More detailsListed by SOTHEBY'S INTERNATIONAL REALTY CANADA- The Living TO Team
- Living TO
- (647)424-0453
- info@livingto.ca
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5 Jean Street in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C13820574
5 Jean Street Toronto M4W 3A6 OPEN HOUSE: Sep 26, 202602:00 PM - 04:00 PM EDTOpen House on Saturday, September 26, 2026 2:00PM - 4:00PMOPEN HOUSE: Sep 27, 202602:00 PM - 04:00 PM EDTOpen House on Sunday, September 27, 2026 2:00PM - 4:00PM
$2,395,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13820574
- Bedrooms:
- 4
- Bathrooms:
- 4
Fall in love with life in North Rosedale-where history, prestige, convenience and nature come together in one of Toronto's most treasured neighbourhoods. Tucked away on a low-traffic dead-end street, this spacious 2-storey detached home offers wonderful character, generous proportions and exceptional flexibility for the way your family wants to live today and in the years ahead. A stone path, lovely landscaping and welcoming veranda set the tone. Step inside to warm wood trim and accents, beautiful leaded and stained glass windows, two wood-burning fireplaces, gracious foyer and handsome staircase-the timeless details that make a house feel like home. With 5 bedrooms, 4 baths, eat-in kitchen and finished basement, there is room to gather, relax, work and play. Move in and appreciate the existing updates for today's lifestyle, or continue to renovate and make it your own. Incorporate the 2nd-floor laundry into an ensuite; imagine the large 2nd-floor room with fireplace as a family room for movie nights; or create a fabulous 3rd-floor primary retreat. Downstairs, enjoy the rec room and full washroom as it is or explore the potential for a separate suite utilizing the side-door entrance. Walk out from the dining room to a large, private backyard made for entertaining and family fun. A detached garage offers rare private parking plus valuable storage. And then there is the lifestyle. Walk around the corner to Summerhill Market, bakery, flower shop, drugstore, dry cleaner and more. Walk on the switchback bridge, stroll to Chorley Park, the Beltline, Rosedale Park with playground, playing fields and winter ice rink or jump into Toronto's remarkable ravine system for hours of walking, running and cycling. Don't miss Evergreen Brick Works with a weekly farmers' market. Coveted neighbourhood public, separate and private schools, TTC at the corner to Rosedale Subway Station and quick driving access downtown complete an exceptional opportunity to put down roots in Rosedale. More detailsListed by ROYAL LEPAGE SIGNATURE REALTY- The Living TO Team
- Living TO
- (647)424-0453
- info@livingto.ca
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Third 18 Castle Frank Crescent in Toronto: Rosedale-Moore Park House for lease (Toronto C09) : MLS®# C13813344
Third 18 Castle Frank Crescent Toronto M4W 3A3
$2,995Residential Freehold- Status:
- For Lease
- MLS® Num:
- C13813344
- Bedrooms:
- 1
- Bathrooms:
- 1
Welcome to 18 Castle Frank, a renovated executive rental ideally located in Rosedale, one of Toronto's most coveted neighbourhoods. This beautiful suite located on a quiet dead end cul-de-sac features a recently renovated kitchen and bathroom that bring modern convenience to the suite. While the open layout allows natural light to flow throughout. Enjoy the private terrace overlooking the private back gardens. The primary bedroom is a generous size with a separate living and dining space with views of the treed front yard. With ensuite laundry, driveway parking, and a large terrace, this suite offers both elegance and functionality. Steps away from the Castle Frank subway station, close proximity to the Danforth and DVP. Located within walking distance to Yonge Street, residents can enjoy easy access to the vibrant shops and restaurants of Rosedale and Summerhill, as well as the upscale amenities of Yorkville and Yonge and Bloor. Gas, water, garbage removal, garden and snow clearing are all included in the rent. Tenants are responsible only for cable/internet and electricity. More detailsListed by ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM- The Living TO Team
- Living TO
- (647)424-0453
- info@livingto.ca
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155 South Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C13816450
155 South Drive Toronto M4W 1S3 OPEN HOUSE: Sep 26, 202602:00 PM - 04:00 PM EDTOpen House on Saturday, September 26, 2026 2:00PM - 4:00PM
$7,895,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13816450
- Bedrooms:
- 5
- Bathrooms:
- 7
155 South Drive - This is the stunning South Rosedale Home you've been looking for! Commandingly positioned on one of the neighbourhood's most coveted streets, directly overlooking the gated beauty of Craigleigh Gardens, sits an exceptional 4+1 bedroom residence on a spectacular 59' x 149' south & west-facing lot. Almost 7,900 sq. ft. of beautifully finished living space, an Elevator to all 4 levels & that almost impossible-to-find 3-car underground garage! Direct & integrated access from your garage to the house - never think about brushing snow off your car again! Everything is perfectly proportioned: The scale. The light. The incredible Soaring 10' ceilings. A generous & wide hallway w/ rich millwork, beautiful hardwood floors & 3 fireplaces set the stage for grand entertaining without ever feeling overly formal. Fabulous living & dining rooms, a gorgeous panelled library/home office, inviting family room & chef's kitchen w/ lg breakfast area & French doors that spill out to the garden. Upstairs, the primary suite is exactly what you want - sitting room with fireplace, 2 walk-in closets, dressing room & spa-like ensuite. Two additional bedrooms each have ensuites, while the sun-filled 3rd floor is something special: a 4th bedroom, sitting room & incredible wraparound sky terrace with breathtaking treetop & Toronto skyline views that are breath taking. And the garden! Completely private, south & west-facing and beautifully landscaped with huge stone terraces, mature cedar hedging & remote-controlled awnings. Summer dinners, cocktails, kids, dogs - there is room for all of it. The walk-out lower level has a rec/media room, gym or 5th bedroom/nanny suite, steam room & mudroom. Steps to Branksome Hall, Rosedale Jr. P.S, T.T.C., ravine trails & parks and minutes to Yorkville & downtown. Elegant yet incredibly livable. This is a rare gem that you won't want to miss. More detailsListed by ROYAL LEPAGE REAL ESTATE SERVICES OXLEY REAL ESTAT- The Living TO Team
- Living TO
- (647)424-0453
- info@livingto.ca
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92 South Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C13813766
92 South Drive Toronto M4W 1R6
$8,990,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13813766
- Bedrooms:
- 5
- Bathrooms:
- 7
A rare opportunity to own a beautifully renovated character home in the heart of Rosedale. This elegant residence offers flawless design, luxurious amenities and every comfort imaginable. Set behind lush landscaping, the home offers striking street presence with a quiet confidence that immediately captures attention. This meticulously maintained home features four plus one bedrooms and seven beautifully designed bathrooms that are complemented by a craftsmanship rarely found. The chef's kitchen is both functional and elegant, featuring a Miele cooktop, Sub-Zero refrigeration, an eat-in area, and a walk-out to an expansive patio. A servery adds thoughtful storage and effortless entertaining appeal. A cozy yet connected family room flows seamlessly into the kitchen. spectacular living room has floor to ceiling glass doors that invite an abundance of light while creating seamless connection between indoor and outdoor living space. This wonderful formal entertainment space flows seamlessly between the living and dining room. The grand dining room offers an impressive setting for formal gatherings and special occasions. The expansive primary bedroom is a true retreat, offering generous space and thoughtful design. A private sitting area provides the perfect spot to unwind with a book or morning coffee while the adjoining dressing room adds a touch of luxury with ample storage space and boutique style organization. The second floor has two additional bedrooms and two bathrooms. The third floor suite has an expansive bedroom, desk, three piece bathroom, walk in closet and plenty of extra room for a seating area. The lower level is complete with heated floor, a media room with wet bar, spa bathroom and sauna. An elevator servicing all floors of the home. Detached two car garage, two additional parking spots, heated walkways and a beautifully landscaped yard. Truly a one of kind Rosedale home. More detailsListed by HARVEY KALLES REAL ESTATE LTD.- The Living TO Team
- Living TO
- (647)424-0453
- info@livingto.ca
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4 Jean Street in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C13815542
4 Jean Street Toronto M4W 3A7
$1,399,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13815542
- Bedrooms:
- 4
- Bathrooms:
- 2
On a tucked-away Rosedale street shared by just a dozen homes, this Arts and Crafts-inspired brick residence offers character, substantial interior space, a deep lot, and several compelling possibilities for its next chapter. With no through traffic, the setting feels notably private. Buyers may choose to renovate the existing home, rework and expand its footprint, or explore the creation of a new custom home, subject to the necessary approvals. Nearly 1,800 square feet above grade, together with approximately 850 square feet in the partially unfinished basement, provides substantial interior space for your plans. The house features four bedrooms, generous principal rooms, 9-ft ceilings on the main floor, a fireplace, a renovated kitchen, and original details that provide a foundation for thoughtful restoration or redesign. A walkout from the kitchen opens to a rear deck and a deep yard, creating generous outdoor space for everyday enjoyment and whatever you envision next. A mutual drive forms part of the existing access and may offer additional possibilities, subject to appropriate due diligence. Permit parking is readily available on the street. Enjoy abundant green space, with Chorley Park, ravine trails, and Evergreen Brick Works nearby. Walk to Summerhill Market and local shops, drive downtown in 8 minutes, or catch the TTC at the corner. Families are also well served by leading public and private schools, including Whitney Junior PS, Branksome Hall and UCC. The value of this property lies in its fundamentals: a well-proportioned brick house, a deep lot, a peaceful residential setting, and the flexibility to pursue your long-term vision - whether that means restoring, reimagining, or rebuilding. For an end user, renovator, builder, or investor, it represents a compelling long-term opportunity in one of Toronto's most established and prestigious neighbourhoods. Property sold "As is/Where is". More detailsListed by RIGHT AT HOME REALTY- The Living TO Team
- Living TO
- (647)424-0453
- info@livingto.ca
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337 Glen Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C13814888
337 Glen Road Toronto M4W 2X4
$1,399,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13814888
- Bedrooms:
- 3
- Bathrooms:
- 2
Best Priced Home In Rosedale! Fully Upgraded Luxury Home in the Highly Sought-After Rosedale-Moore Park Community. Originally a 3-Bedroom Semi-Detached, This Home Has Been Converted to 2 Spacious Bedrooms. This Exceptional Residence Features a Brand-New Custom Kitchen With Butcher Block Countertops, Designer Backsplash, Ceramic Tile Flooring, Premium Stainless Steel Appliances, and a Walkout to a Private Deck Perfect for Relaxing or Entertaining. The Renovated Bathrooms Offer Stylish Subway Tile Surrounds and Elegant Ceramic Flooring, While Hardwood Floors, Pot Lights, and Fresh Neutral Paint Create a Bright, Modern Atmosphere Throughout the Home. The Open-Concept Living and Dining Area Is Thoughtfully Designed for Comfortable Everyday Living and Effortless Entertaining. The Entire Third Floor Is Dedicated to a Private Primary Retreat Featuring a Spa-Inspired Ensuite and an Expansive Mirrored Closet. The Fully Finished Basement Offers a Spacious Recreation Room, Additional Space Ideal for a Bedroom, Home Office, or Gym, and a Separate Entrance for Added Flexibility. A Brand-New High-Efficiency Furnace and a Brand-New A/C Unit Has Just Been Installed. Step Outside to a Tranquil, Fully Fenced Backyard Oasis Surrounded by Mature Trees, Offering Exceptional Privacy and a Peaceful, Zen-Like Setting Perfect for Outdoor Living and Entertaining. Ideally Located Just Steps From Chorley Park, Scenic Ravine Trails, Evergreen Brick Works, Top-Rated Schools, Upscale Grocers, Boutique Shops, Cafés, and Convenient TTC Access, This Home Offers the Perfect Blend of Luxury, Nature, and Urban Convenience in One of Toronto's Most Prestigious Neighbourhoods. ***Please Note: The Listing Photos Have Been Enhanced With AI To Show Potential Décor And Layout Ideas. The Property's Structure Is Accurately Shown, But The Interiors Are Virtually Staged. This Is To Help Envision Possibilities, Not To Reflect Actual Furnishings*** More detailsListed by INTERNATIONAL REALTY FIRM, INC.- The Living TO Team
- Living TO
- (647)424-0453
- info@livingto.ca
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Condo Apartment in Toronto
Residential Condo & Other- The Living TO Team
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Data was last updated September 24, 2026 at 07:15 PM (UTC)