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.
Search All Available Properties
Rosedale Listings
-
23 South Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12102765
23 South Drive Toronto M4W 1R2 
$7,654,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12102765
- Bedrooms:
- 5
- Bathrooms:
- 5
Set on an extraordinary 50 ft x 292 ft ravine lot with spectacular park-like vistas, this architecturally distinct 5-bedroom home in South Rosedale blends classic heritage charm and modern design. It offers exceptional privacy and tranquility in the heart of the city. Behind its stately Rosedale façade lies an extraordinary interior where light, scale, and playful sophistication converge. The main floor features a gracious living room with fireplace and an oversized dining room. The dramatic two-storey atrium forms the heart of the home, seamlessly connecting indoor and outdoor living. Complementing the atrium, a nearby room with a second wood-burning fireplace adds warmth and versatility perfect as a media room, office, or creative space. The lower level opens onto a stone patio that flows seamlessly into the landscaped gardens. Beyond lies a generous stretch of tableland offering endless possibilities a soccer field, hockey rink and other recreational uses, or simply left in its natural state for a serene, nature conservation-style retreat. The upper floors offer five spacious bedrooms and include a primary suite with a sitting area, bay windows, wood-burning fireplace, and ensuite bath. Topped off with a private driveway, this home delivers rare convenience and charm. Located just minutes from Yonge, Rosedale, Summerhill, and some of Torontos top schools, this property is a truly rare opportunity to own a piece of architectural artistry in one of the citys most coveted neighbourhoods. More detailsListed by RE/MAX WEST REALTY INC.- The Living TO Team
- Living TO
- (647)424-0453
- info@livingto.ca
-
23 South Drive in Toronto: Rosedale-Moore Park House for lease (Toronto C09) : MLS®# C12102786
23 South Drive Toronto M4W 1R2
$19,000Residential Freehold- Status:
- For Lease
- MLS® Num:
- C12102786
- Bedrooms:
- 5
- Bathrooms:
- 5
Set on an extraordinary 50 ft x 292 ft ravine lot with spectacular park-like vistas, this architecturally distinct 5-bedroom home in South Rosedale blends classic heritage charm and modern design. It offers exceptional privacy and tranquility in the heart of the city. Behind its stately Rosedale façade lies an extraordinary interior where light, scale, and playful sophistication converge. The main floor features a gracious living room with fireplace and an oversized dining room. The dramatic two-storey atrium forms the heart of the home, seamlessly connecting indoor and outdoor living. Complementing the atrium, a nearby room with a second wood-burning fireplace adds warmth and versatility perfect as a media room, office, or creative space. The lower level opens onto a stone patio that flows seamlessly into the landscaped gardens. Beyond lies a generous stretch of tableland offering endless possibilities a soccer field, hockey rink and other recreational uses, or simply left in its natural state for a serene, nature conservation-style retreat. The upper floors offer five spacious bedrooms and include a primary suite with a sitting area, bay windows, wood-burning fireplace, and ensuite bath. Topped off with a private driveway, this home delivers rare convenience and charm. Located just minutes from Yonge, Rosedale, Summerhill, and some of Torontos top schools, this property is a truly rare opportunity to own a piece of architectural artistry in one of the citys most coveted neighbourhoods. More detailsListed by RE/MAX WEST REALTY INC.- The Living TO Team
- Living TO
- (647)424-0453
- info@livingto.ca
-
68 Nesbitt Drive in Toronto: Leaside House for sale (Toronto C11) : MLS®# C12101904
68 Nesbitt Drive Toronto M4W 2G3
$1,299,999Residential Freehold- Status:
- Active
- MLS® Num:
- C12101904
- Bedrooms:
- 3
- Bathrooms:
- 3
Perfect opportunity to own a detached home in one of the most desirable neighborhoods of the city for an accessible price! This charming brick bungalow is an absolute gem. You will love its peaceful atmosphere nestled among mature trees and surrounded by walking trails and parks, ideal for nature lovers. Enjoy all the amenities city living can offer with outstanding schools, shops and downtown Toronto just minutes away. This home has been lovingly maintained and is move in ready as a starter home. It features a new energy efficient heat-pump and furnace. The finished basement has a separate entrance and can easily be converted into a separate suite for additional income to make home ownership more affordable. This can also be the perfect location where you can build your dream home. More detailsListed by RED HOUSE REALTY- The Living TO Team
- Living TO
- (647)424-0453
- info@livingto.ca
-
43 Douglas Crescent in Toronto: Leaside House for sale (Toronto C11) : MLS®# C12099631
43 Douglas Crescent Toronto M4W 2E6
$9,000,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12099631
- Bedrooms:
- 4
- Bathrooms:
- 5
Nestled into the trees, this spectacular Rosedale home has been totally reimagined and redesigned, creating a home quite unique for Toronto. The ravine lot is an expansive 50x127.66 lot with additional green space at the rear, backing onto the abandoned rail line that leads to the Evergreen Brickworks. Incredible four seasons living, watching the wildlife outside your windows; truly an oasis in the city. As seen right now in Elle Decor UK, will be featured in Architectural Digest, and the Local Project in upcoming issues. Every ounce of the home showcases the best in materials and craftsmanship; a total renovation of this L shaped mid century modern home was undertaken, including new triple glazed windows, doors, and skylights, new roof, new heating and cooling systems with in-floor heating throughout the house in addition to forced air heating and cooling. An expansive glycol heating system for winter for the driveway, front pathway, side pathway, and entire inner courtyard surrounding the beautiful year-round Gunite pool and whirlpool. Limestone (sourced from Kentucky) pool deck, specimen trees create incredible privacy, an outdoor kitchen has been built on the expansive Ipe deck at the rear of the property from which to watch the seasons change. The best materials have been curated for the kitchen and washrooms; onyx, rare marbles, and designer finishes. The kitchen offers top of the line appliances, designed with a chef in mind. The whole house has been insulated and waterproofed with a new weeping tile system, sump pump, and backflow preventer. New Moncer oak hardwood floors have been installed throughout, and new light fixtures have been carefully chosen. The all new Creston system, audiovisual and components, offers the latest in smart home technology. This is an exquisite and rare offering, a calm retreat in our vibrant and busy city. Walk to Summerhill Market and shops, walk to area schools (Bennington Heights, Bessborough Drive Leaside HS, Branksome Hall). More detailsListed by ROYAL LEPAGE/J & D DIVISION- The Living TO Team
- Living TO
- (647)424-0453
- info@livingto.ca
-
53 Maple Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12095664
53 Maple Avenue Toronto M4W 2T9
$3,350,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12095664
- Bedrooms:
- 5
- Bathrooms:
- 4
Welcome to 53 Maple Avenue: a home rich in history, nestled on a picturesque, tree-lined street in South Rosedale. This home blends historic charm with thoughtful updates and offers expansive principal rooms, providing a sense of grandeur and sophistication throughout. With four generously sized bedrooms and four bathrooms, this property is ideal for family living. Spanning over 3,000 square feet above grade, plus an additional 1,000 square feet in the lower level, there is no shortage of space to accommodate your lifestyle. The home has been thoughtfully updated to meet the highest standards, including a brand-new roof, a beautifully re-modelled kitchen, and upgraded bathrooms. Additionally, all windows and doors have been replaced with premium Ridley products, ensuring both energy efficiency and style. Situated in one of Toronto's most coveted neighborhoods, this residence boasts an enviable location with convenient parking. It is just steps away from prestigious private schools such as Branksome Hall, Mooredale, and Montcrest, as well as top-rated public schools like Rosedale Public School. The home is also within walking distance to lush green spaces like Craigleigh Gardens and the scenic Rosedale Ravine System, offering peaceful retreats in the heart of the city. Plus, easy access to the TTC subway ensures that you are well-connected to all the amenities Toronto has to offer. Ready for immediate occupancy, this stunning property offers a seamless move-in experience and is situated in a family-friendly community that will provide years of comfort and enjoyment. Don't miss the opportunity to make this exceptional home your own. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- The Living TO Team
- Living TO
- (647)424-0453
- info@livingto.ca
-
4 Meredith Crescent in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12094920
4 Meredith Crescent Toronto M4W 3B6
$5,495,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12094920
- Bedrooms:
- 5
- Bathrooms:
- 5
Set in the heart of coveted Rosedale, this elegantly renovated home offers timeless sophistication on an exceptional 50-foot frontage. Perched at the top of a rare south-facing lot with sweeping, unobstructed skyline views, the property effortlessly blends privacy and prestige in one of Toronto's most storied neighbourhoods. A long private driveway with ample parking and a detached 1.5-car garage provides great convenience, an uncommon luxury in the area. The home's refined interior marries classic architectural detail with thoughtfully curated modern updates, creating a warm yet elevated living experience across every room. Your gracious third-floor primary suite features a separate sitting room or library. Walk out from your lower level into the flat backyard oasis, and sit in front of the fire pit on a cozy evening. This home is perfectly positioned just a short stroll from Bloor Street's boutiques, fine dining and within short walking distance of Branksome Hall. This home is ideal for families seeking both top-tier education and vibrant city living. Commuters will appreciate seamless access via Mt. Pleasant Road and nearby transit routes, making daily travel effortlessly efficient. With its generous proportions, elegant curb appeal, and exquisite renovations, this Rosedale gem is a rare offering for those who value location, luxury, and lifestyle in equal measure. More detailsListed by ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM- The Living TO Team
- Living TO
- (647)424-0453
- info@livingto.ca
-
68 Rowanwood Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12094739
68 Rowanwood Avenue Toronto M4W 1Y9
$7,999,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12094739
- Bedrooms:
- 8
- Bathrooms:
- 4
Exquisitely renovated South Rosedale Residence located on a coveted street, just a short stroll from Yonge St. This distinguished, designer's own home exudes timeless elegance & thoughtful design on every level & was reimagined by Baldwin & Franklin Architects with a substantial addition & renovation. A wide 45 ft lot with private drive, detached 2 car garage & stunning landscaping by Janet Rosenberg plus over 5000 sq ft of living space make this home perfectly turnkey for family living. A beautiful home made for entertaining with large principal rooms & gracious proportions. The sun-filled, south-facing living & dining rooms are anchored by a carved limestone gas fireplace, a bay window & a walk out to the manicured front garden a truly serene setting.The kitchen is appointed with high-end appliances, marble countertops & a large centre island. Enjoy the open-concept breakfast area & family room - an ideal setting for hosting.The 2nd level features a luxurious primary retreat with a walk-in closet, a 5-pc spa like ensuite bath & a private terrace. A secondary family room with a gas fireplace along with a beautifully appointed office with custom built-ins, complete this sophisticated level.The 3rd floor features generously proportioned bedrooms, a 3-pc bathroom & a flexible bonus space usable as a 5th bedroom, homework zone, or office.The fully finished lower level has a spacious rec room, a wine cellar equipped with 4 full-sized wine fridges, a laundry room & 2 additional rooms could be used as bedrooms or as an exercise room. Step outside into your private, beautifully landscaped backyard by Janet Rosenberg an entertainers dream with a flagstone patio with seating area, a manicured yard, accent lighting & mature trees lining the perimeter for privacy.Ideally located walking distance to local shops & restaurants, Branksome & Rosedale Ps, TTC, beautiful Ravine trails & Parks. A true Rosedale classic- rare in scale, rich in character & designed for modern living. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- The Living TO Team
- Living TO
- (647)424-0453
- info@livingto.ca
-
8 Binscarth Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12095853
8 Binscarth Road Toronto M4W 1Y1 OPEN HOUSE: Apr 26, 202502:00 PM - 04:00 PM EDTOpen House on Saturday, April 26, 2025 2:00PM - 4:00PMOPEN HOUSE: Apr 27, 202502:00 PM - 04:00 PM EDTOpen House on Sunday, April 27, 2025 2:00PM - 4:00PM
$8,800,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12095853
- Bedrooms:
- 8
- Bathrooms:
- 6
Classic North Rosedale family home embodies graciousness and grandeur, situated on one of the neighborhoods most sought-after streets. With over 6300 square feet of living space, including a lower level, it features 7 bedrooms, and 6 bathrooms, making it perfect for family living and entertaining. Elegant architectural design blends with meticulous restoration and modern finishes, creating exceptional living space. The formal living and dining rooms, with their high ceilings, wood-burning fireplaces, plaster crown moldings, leaded pane glass windows and French doors, create a stunning backdrop for memorable entertaining. The impressive gourmet kitchen, equipped with top-of-the-line appliances, custom cabinetry, and a charming breakfast area perfectly balances form and function. For more casual gatherings, the family room seamlessly connects to a covered porch, offering a cozy yet stylish setting for everyday enjoyment. The primary suite offers a relaxing retreat, featuring spacious walk-in dressing room and a luxurious marble ensuite bath. Completing the private accommodations are two additional bedrooms, an office, and the convenience of second-level laundry, along with three bedrooms on the third level. The lower level adds even more value with a playroom, nanny's room, exercise room, and ample storage cellar. Exquisitely landscaped gardens, mature trees, and sparkling pool accented by wrought iron arbors create a magical paradise. The homes prime location near schools, (OLPH & Whitney School District), Rosedale Park, local shopping, and public transit complete the amenities of this unique opportunity. More detailsListed by HARVEY KALLES REAL ESTATE LTD.- The Living TO Team
- Living TO
- (647)424-0453
- info@livingto.ca
-
305 Glen Road in Toronto: Rosedale-Moore Park House for lease (Toronto C09) : MLS®# C12097083
305 Glen Road Toronto M4W 2X4
$12,750Residential Freehold- Status:
- For Lease
- MLS® Num:
- C12097083
- Bedrooms:
- 5
- Bathrooms:
- 5
Located in one of Toronto's most coveted neighbourhoods, 305 Glen Rd. in North Rosedale is a testament to modern sophistication. Designed and re-imagined by renowned architect, Richard Wengle and fully re-built, top to bottom in 2020, this home has it all. A must see for anyone looking for all the Bells and Whistles. Situated just steps to Chorley Park, bustling Summerhill Market, scenic ravines, Evergreen Brickworks and yet on a quiet dead end residential street with a private, fully fenced backyard. Scavolini kitchen and baths, SubZero fridge, Wolf range, built in speakers, security system, wall-to wall wine cellar, heated floors and automated blinds are just a few of the many features in this executive rental. An exquisitely finished, full height basement with wall to wall windows and walk-out to a fully landscaped backyard with firepit is an entertainer's paradise. More detailsListed by LIONHEART REALTY- The Living TO Team
- Living TO
- (647)424-0453
- info@livingto.ca
-
68 Astley Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12095465
68 Astley Avenue Toronto M4W 3B4
$3,395,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12095465
- Bedrooms:
- 6
- Bathrooms:
- 5
Welcome to North Rosedale -A Rare Opportunity in a Coveted, Historic Community. Nestled in the heart of prestigious North Rosedale, this elegant 3-storey residence offers timeless charm and exceptional space for refined family living. Featuring 5 bedrooms, 5 bathrooms, and a private nanny suite in the lower level, this home seamlessly blends classic character with modern comforts.The main floor boasts a formal dining room with custom built-ins, a spacious family room combined with an open-concept kitchen, and a sunlit breakfast room perfect for casual meals. The living room exudes warmth, complete with a fireplace, bay window, and serene views of the front yard.Upstairs, the primary retreat features a luxurious 5-piece ensuite and an expansive walk-in closet, while the upper levels offer two private terraces, ideal for outdoor entertaining or quiet relaxation. Lush yard with a peaceful pond and beautifully landscaped garden.Natural light fills every corner of this home, enhancing its bright, welcoming ambiance. Located just steps from Chorley Park, Summerhill Market, and all of Rosedale's top-tier amenities, this is a rare opportunity to own in one of Torontos most distinguished neighborhoods. More detailsListed by SOTHEBY`S INTERNATIONAL REALTY CANADA- The Living TO Team
- Living TO
- (647)424-0453
- info@livingto.ca
-
1727-33 Bayview Avenue in Toronto: Leaside Commercial for sale (Toronto C11) : MLS®# C12097099
1727-33 Bayview Avenue Toronto M4G 3C1
$5,600,000 /For SaleCommercial- Status:
- Active
- MLS® Num:
- C12097099
- Total Area:
- 5,557 sq. ft.
Opportunity to own. Prime Leaside property with 52.47 ft frontage. Located near future LRT station. Total Site Area 5,557 sq ft (as per MPAC). (3) Street front commercial stores (fully leased), with basement(s), and (6) apartments on 2nd level ((2) 1 Bedrooms + (4) Bachelor apartments). Buyer to assume existing Tenancies. Properties must be sold together. VTB First Mortgage - TBN More detailsListed by SLAVENS & ASSOCIATES REAL ESTATE INC.- The Living TO Team
- Living TO
- (647)424-0453
- info@livingto.ca
-
56 Roxborough Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12092726
56 Roxborough Drive Toronto M4W 1X1
$4,900,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12092726
- Bedrooms:
- 4
- Bathrooms:
- 3
Stairway to heaven, 56 Roxborough Dr. sits on a simply sublime 110 x 129 ravine lot nestled on top of the Roxborough hillside, offering an unparalleled experience in privacy & natural splendour, a tree top sanctuary, the likes of which cannot be duplicated in Rosedale. The home is completely surrounded by a magnificent stone Terrace, designed by Mark Hartley, & crafted completely in Wiarton stone by true stone masons. This expansive Terrace will entice you to indulge in a coffee while reading a good book, a glass of wine, or al fresco dining under the trees with friends & loved ones. The existing home has been taken back to studs & is ready for its new owner to create their vision for this treetop escape, a true blank canvas for someone with vision who doesn't want to inherit, or pay for someone else's choices. **EXTRAS** This property is for someone who is seeking an urban retreat, yet desires privacy, an intellectual, a writer, an artist or a great thinker who appreciates peaceful surroundings & being wrapped in Mother Nature's arms. More detailsListed by SOTHEBY`S INTERNATIONAL REALTY CANADA- The Living TO Team
- Living TO
- (647)424-0453
- info@livingto.ca
Data was last updated April 25, 2025 at 03:15 AM (UTC)