Find Homes for Sale in Rosedale, Toronto, Canada
Welcome to the premier resource for finding homes in Rosedale, one of Toronto’s most prestigious neighborhoods. Our exclusive listings feature a variety of luxurious properties, perfect for those seeking an upscale and elegant living experience. Discover the charm and sophistication of Rosedale and find your ideal home with our curated selection, detailed information, and expert guidance.
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63 Astley Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C14121724
63 Astley Avenue Toronto M4W 3B5 
$2,149,000Residential Freehold- Status:
- Active
- MLS® Num:
- C14121724
- Bedrooms:
- 4
- Bathrooms:
- 2
A Ravine Retreat on a Quiet Rosedale Street! This beautifully renovated modern 3+1 bedroom, 2 bathroom detached gem sits on a quiet North Rosedale street, backing onto a breathtaking ravine with no neighbours behind, just nature & total tranquility. Modern living shines the moment you arrive, with a private parking pad, freshly landscaped front, custom stone planter wall framing lush perennial gardens & a charming covered porch. Inside, the bright open concept main floor shines with modern finishes, pot lights & a brand new remote controlled gas fireplace set in custom cabinetry. A large new picture window with smart electric roller blinds frames the tree lined street. The chef's kitchen will win your heart, with a massive Sub Zero fridge, gas range, wine & beer fridge, butcher block counters, magnetic knife wall, reverse osmosis water filter & breakfast bar, plus a separate dining room for hosting. Double doors open to a huge composite deck overlooking the ravine, a private retreat that's stunning in every season. Upstairs, new runners lead to three bedrooms, including a spacious primary & a large second bedroom with custom built ins, plus a renovated spa inspired bathroom. The finished lower level delivers a fourth bedroom with a walk in closet & bathroom, a professional office with a drilled in safe, a play & TV area, laundry tucked behind custom cabinetry & a secret reading nook under the stairs the kids will love. Fully smart enabled, with a facial recognition front lock, Ring alarm & camera, smart thermostat, app controlled fireplace, blinds & lights, plus USB C ports & network hubs throughout. Built for the future, with second floor supports, upgraded HVAC & capped ducts in place for a potential third storey or rear addition (buyer to verify). Steps to Summerhill Market, Chorley Park, ravine trails & Evergreen Brick Works, near top public & private schools. Rick Astley promised he'd never give you up. Once you're home on Astley, you won't either. More detailsListed by SAGE REAL ESTATE LIMITED- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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39 Standish Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C14120018
39 Standish Avenue Toronto M4W 3B2
$1,980,000Residential Freehold- Status:
- Active
- MLS® Num:
- C14120018
- Bedrooms:
- 6
- Bathrooms:
- 4
Three Distinct Paths. One Exceptional Rosedale Address. In one of Toronto's most coveted neighbourhoods, this versatile property presents a rare opportunity at a price point seldom found in Rosedale. With three self-contained units and an attractive existing income stream, the property offers a choice of possibilities, each with its own appeal. For those envisioning a substantial single-family residence, the property offers the opportunity to reimagine the existing footprint and create a home tailored to your vision, in an established neighbourhood renowned for its tree-lined streets and excellent schools. Alternatively, enjoy a more manageable living space while retaining two tenanted units to generate income and help offset carrying costs. A compelling proposition for those seeking a foothold in Rosedale without the commitment of a larger home. For the investor, the existing configuration and rental income offer an opportunity to acquire a multi-unit property in a premier location, with flexibility for the future. Whether your plans are to transform, occupy and earn, or invest and hold, the possibilities are as appealing as the address itself. More detailsListed by ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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House in Toronto
Residential Freehold- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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106 Highland Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C14107036
106 Highland Avenue Toronto M4W 2A6
$3,629,000Residential Freehold- Status:
- Active
- MLS® Num:
- C14107036
- 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- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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50 Nanton Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C14095964
50 Nanton Avenue Toronto M4W 2Y9 OPEN HOUSE: Nov 01, 202602:00 PM - 04:00 PM EDTOpen House on Sunday, November 1, 2026 2:00PM - 4:00PM
$5,295,000Residential Freehold- Status:
- Active
- MLS® Num:
- C14095964
- Bedrooms:
- 6
- Bathrooms:
- 4
A magnificent Rosedale Grand Dame! Set majestically on an exceptional 50' x 150' lot in coveted South Rosedale, this distinguished red-brick residence offers extraordinary proportions, timeless elegance & undeniable presence. Rich in architectural character, w/soaring ceilings, natural light & beautifully scaled principal rooms, this is a home that captures the grandeur of a bygone era. Six generous bedrooms provide wonderful space for a growing family, while gracious entertaining rooms set the stage for memorable gatherings. A home of substance & character, where generations can gather & cherished memories unfold. The magnificent 150' deep property is equally compelling. A rare circular driveway creates a gracious arrival, while a garage w/ direct access to the rear garden adds everyday convenience. Beyond, a private backyard oasis awaits, w/an inground pool, expansive outdoor entertaining space & ample room for children to play. An extraordinary setting for summer afternoons by the pool, family celebrations & evenings under the stars. Nestled on one of South Rosedale's most desirable, family-friendly streets, where children grow up together, neighbours become lifelong friends & a beloved annual street party celebrates a wonderful sense of community. Just steps to Branksome Hall & a short stroll to Rosedale Junior Public School, Castle Frank subway, neighbourhood shops & restaurants. Lovingly preserved, w/remarkable original character & exceptional bones, 50 Nanton presents an increasingly rare opportunity: move in & enjoy its timeless charm, or undertake a thoughtful transformation to create a spectacular residence for generations to come. Grand in scale, gracious in spirit & extraordinary in potential. A landmark Rosedale residence marrying old-world elegance, family warmth & an enviable lifestyle. Properties of this stature, on lots of this significance, are seldom available. An exceptional opportunity to write the next chapter of a magnificent home. More detailsListed by ROYAL LEPAGE REAL ESTATE SERVICES OXLEY REAL ESTATE- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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29 Standish Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C14081856
29 Standish Avenue Toronto M4W 3B2
$2,879,000Residential Freehold- Status:
- Active
- MLS® Num:
- C14081856
- Bedrooms:
- 4
- Bathrooms:
- 4
A Private Retreat. An Extraordinary Setting. Tucked Away On One Of North Rosedale's Most Coveted Streets, Just Steps From Beautiful Chorley Park, This Exceptional 3+1 Bedroom, 3.5-Bathroom Detached Home Offers A Rare Combination Of Space, Privacy And Timeless Elegance. Surrounded By Mature Trees And The Natural Beauty Of The Rosedale Ravine, The Setting Feels Remarkably Peaceful, Yet Remains Connected To Everything The City Has To Offer. Inside, Generous Principal Rooms Provide Wonderful Spaces For Both Everyday Family Living And Entertaining, Including A Formal Living Room, Inviting Family Room And Three Wood-Burning Fireplaces That Add Warmth And Character Throughout. The Well-Appointed Kitchen Features Premium Appliances, Including A Viking Gas Range And Oven, While The Excavated Lower Level Offers Impressive Ceiling Height And Exceptional Versatility, With An Additional Bedroom, Kitchenette And Separate Side Entrance, Ideal For Guests Or Nanny Accommodations. Outdoors, Discover A Truly Spectacular Backyard Oasis. Beautifully Landscaped And Exceptionally Private, This Inviting Retreat Features Mature Trees, Lush Gardens, Thoughtfully Designed Dining And Seating Areas, Outdoor Lighting And A Fire Pit For Memorable Evenings Outdoors. Complete With Private Parking For One Car, And Just A Short Stroll To Chorley Park's Scenic Walking Trails, Summerhill Market, Excellent Schools And Neighbourhood Amenities, This Is A Rare Opportunity To Enjoy The Serenity Of North Rosedale Without Sacrificing The Convenience Of City Living. An Extraordinary Home In An Equally Extraordinary Setting. Let Your Next Chapter Begin. More detailsListed by RE/MAX HALLMARK REALTY LTD.- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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94 Roxborough Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C14027922
94 Roxborough Drive Toronto M4W 1X1
$4,650,000Residential Freehold- Status:
- Active
- MLS® Num:
- C14027922
- Bedrooms:
- 3
- Bathrooms:
- 3
A rare blend of sophistication, privacy & serenity at 94 Roxborough Drive, an extraordinary North Rosedale residence. Nestled beneath a lush canopy of mature trees with no immediate houses on either side, this architectural gem offers a peaceful retreat just minutes from downtown. Originally built in the 1950s by Howard Chapman, son of renowned Canadian architect Alfred Chapman, the home was extensively renovated in 2021, marrying its architectural heritage with contemporary design & exceptional craftsmanship. Spanning approximately 3,000 sq. ft., light-filled interiors feature refined entertaining spaces, 3 beautifully appointed full bathrooms & flexible bedroom configurations. At the heart of the home, a spectacular custom kitchen boasts a 13' island, 8' picture window overlooking the forest-like gardens, Canadian granite counters, bespoke cabinetry, Wolf gas cooktop, steam oven, warming drawer & Miele dishwasher. The adjoining great room evokes the warmth of a luxurious modern chalet, with soaring ceilings, loft, gas fireplace & white oak flooring. Architectural details include a marble foyer, bevelled-glass entry, designer lighting & sculptural staircase. The private upper-level primary suite offers a luxurious ensuite, separate shower room & elegant dressing room. A versatile office or additional bedroom enjoys tranquil treetop views. A secluded side terrace provides an intimate setting for outdoor dining & entertaining. Automatic blinds, 1.5-car garage & private double driveway add everyday convenience. Featured in an international architecture publication & luxury home series, this remarkable property offers the presence of a larger estate without its maintenance demands. Steps to Summerhill Market & ravine trails, with Yonge St., transit, shops & fine dining nearby. A rare opportunity to own an exceptional North Rosedale sanctuary where architecture, nature & urban living exist in perfect harmony. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
-
House in Toronto
Residential Freehold- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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please create a free account -
20 Cluny Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C13861210
20 Cluny Drive Toronto M4W 2P7
$11,995,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13861210
- Bedrooms:
- 5
- Bathrooms:
- 7
Discreetly positioned on one of Rosedale's most prestigious streets, this exceptional ravine residence offers rare architectural scale, privacy, andcontemporary refinement. Set on a remarkable 238-foot deep lot backing onto the Rosedale ravine, the property boasts a resort-like setting withan infinity-edge pool, expansive outdoor living areas, and a covered terrace designed for year-round entertaining. Situated minutes fromdowntown Toronto, Rosedale is a unique combination of charm and sophistication. It offers upscale dining, designer shopping, top-rated publicand private schools, beautiful parks and endless trails for walking, running or cycling. Quick access to the subway system, Yonge Street andMount Pleasant Road allow for easy access to explore all that Toronto has to offer. 20 Cluny has been thoughtfully renovated to reflect aseamless blend of timeless architecture and modern luxury. This home spans over 6,000 square feet above grade, with a fully finished lowerlevel, providing elegant space for both grand entertaining and comfortable family living. Inside, 11-foot ceilings on the main and third floorsenhance light and volume, while expansive principal rooms offer sophisticated living and dining spaces. The main level, exceeding 2,200 squarefeet, features a functional layout with formal living and dining rooms, a private office, and a kitchen and breakfast area that connect effortlesslyto the terrace and gardens. Upper levels include five generously sized bedrooms, each with its own ensuite. The primary suite offers a sereneretreat with a dressing room and spa-inspired bathroom. The third floor provides rare additional living space, ideal for guests or multi-generational living. The lower level includes a recreation room, home gym, and wet bar. Complete with a spacious double garage and heateddrive, this elegant home presents a rare opportunity in one of Toronto's most prestigious neighbourhoods. More detailsListed by ROYAL LEPAGE REAL ESTATE SERVICES PHINNEY REAL EST- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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114 Glen Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C13864318
114 Glen Road Toronto M4W 2V9
$9,880,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13864318
- Bedrooms:
- 8
- Bathrooms:
- 8
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 More detailsListed by HARVEY KALLES REAL ESTATE LTD.- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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4 Douglas Crescent in Toronto: Leaside House for sale (Toronto C11) : MLS®# C13854620
4 Douglas Crescent Toronto M4W 2E7
$4,999,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13854620
- Bedrooms:
- 5
- Bathrooms:
- 5
You don't want to miss this one! Welcome to 4 Douglas Crescent, a truly exceptional architectural home on the edge of North Rosedale, offering 4+1 bedrooms, 5 bathrooms, and a remarkable blend of luxury, innovation, and functionality. Featuring hickory wide-plank flooring, heated marble floors, 9 skylights, custom lighting, Control4 automation, smart glass windows, extensive security, and 50+ surround-sound speakers, every detail has been thoughtfully designed. The backyard is pre-wired and pre-plumbed for a BBQ, hot tub, fire and water features, while the impressive garage offers a 6,000-lb. car lift, heated floors, EV charger, car-wash setup, and heated driveway with parking for four. A rare turnkey opportunity in one of Toronto's most exclusive neighborhoods. More detailsListed by HARVEY KALLES REAL ESTATE LTD.- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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400 Summerhill Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C13849692
400 Summerhill Avenue Toronto M4W 2E4
$1,819,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13849692
- Bedrooms:
- 6
- Bathrooms:
- 5
Rarely offered Rosedale-Moore Park investment opportunity! This exceptional freehold commercial-residential property offers outstanding flexibility for end users, investors in one of Toronto's most desirable, walkable neighborhoods. The building comprises four updated units: one street-level commercial space (currently occupied by a busy veterinary clinic with excellent street exposure) and three residential suites above/below, offering varied layouts that support strong rental demand and stable tenancy. Separately metered for added efficiency and long-term flexibility. Ideal for an investor seeking reliable income, or a buyer looking to live in one unit while generating meaningful cash flow from the others. Parking for 3+ cars is a rare bonus in the area. Steps to Summerhill Market, parks, top schools, shops, TTC, and Bike Share-an iconic community that truly feels like an oasis in the city. Shows to perfection. More detailsListed by HOMELIFE/VISION REALTY INC.- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
Data was last updated October 28, 2026 at 04:15 AM (UTC)
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