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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4 Maple Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12384091
4 Maple Avenue Toronto M4W 2T6 
$6,295,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12384091
- Bedrooms:
- 16
- Bathrooms:
- 10
A rare opportunity in prestigious South Rosedale. This unique sixplex spans over 9,000 sq. ft. with one legal address (4 Maple Ave) and two municipal addresses (4 Maple Ave & 43 Elm Ave). Configured as two conjoined buildings, it offers exceptional flexibility for investors, multi-generational living, or conversion to a luxury single-family residence. With six spacious suites, soaring ceilings, private outdoor spaces, and elegant period details, the property blends character with strong income potential. 43 Elm is vacant, providing immediate opportunity for luxury redevelopment, boutique leasing, or owner occupation. Steps to Branksome Hall, ravines, parks, Yonge St. shopping & dining, plus easy access to Sherbourne, Castle Frank, and Rosedale subway stations. Yorkville is just a short walk via the Glen Road Bridge. Offering the perfect balance of prestige, space, location, and income, this is a one-of-a-kind asset in one of Torontos most sought-after neighbourhoods. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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42 True Davidson Drive in Toronto: Leaside House for sale (Toronto C11) : MLS®# C12381558
42 True Davidson Drive Toronto M4W 3X5
$3,150,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12381558
- Bedrooms:
- 6
- Bathrooms:
- 4
Welcome to 42 True Davidson, a captivating 6-bedroom residence nestled within the highly sought-after community of Governors Bridge. Upon entering, you'll be greeted by a seamless blend of classic elegance and modern sophistication. Soaring ceilings, sleek hardwood floors, and crown molding create an atmosphere of openness and airiness. The home boasts 6 generously sized bedrooms, providing ample space for everyone, along with four bathrooms to ensure effortless mornings. The master retreat is a haven of indulgence, complete with an opulent ensuite and two expansive walk-in closets perfect for any wardrobe. The heart of the home is the stunning great room with a wooden fireplace, an ideal space for creating lasting memories with loved ones. Through double doors, the dining room connects seamlessly to the kitchen through the servery, creating an ideal flow for entertaining. The chef-inspired eat-in kitchen is a true culinary dream and ties into the family room with an expansive deck that seamlessly extends your entertaining area. The lower level awaits your personal touch - envision a state-of-the-art home gym, a private theatre, or a vibrant playroom. Additional features include a spacious mudroom designed to keep clutter at bay, and a recreation room perfect for play or relaxation. At 42 True Davidson, experience the perfect fusion of luxury living, natural beauty, and a prime location. 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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49 Roxborough Street in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12381772
49 Roxborough Street Toronto M4W 1V5 OPEN HOUSE: Sep 07, 202502:00 PM - 04:00 PM EDTOpen House on Sunday, September 7, 2025 2:00PM - 4:00PMOPEN HOUSE: Sep 07, 202502:00 PM - 04:00 PM EDTOpen House on Sunday, September 7, 2025 2:00PM - 4:00PM
$3,925,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12381772
- Bedrooms:
- 3
- Bathrooms:
- 4
Welcome to this most iconic ivy clad stone home in prime heritage Southwest Rosedale.The original house was built circa 1905 and later had a first and second floor addition undertaken. The property enjoys a private driveway.This majestic home is set well back on its property of 45' x 100'. The property is on a south lot with a lovely outdoor terrace and steps down to a manicured English garden. The private terrace and garden enjoy a lovely water feature with a small pond. There is a charming garden shed that frames the back of the garden.On the main floor are found the kitchen and open eat in area with a box bay window and with excellent circular flow to the dining room with hardwood floors and fireplace. The living room is at the rear and overlooks the garden. There are French doors from the kitchen and the living room out to the flagstone terrace. The kitchen also enjoys pretty views of the front garden. On the main floor is a powder room. For the romantics there is a covered front porch with ionic columns and a built-in swing overlooking the front of the property. On the second floor is the large family room with south exposure and lush treed views. On the second floor is the primary bedroom with a sitting area and a 3-piece bathroom. There is a large walk-in closet opposite to the primary bedroom. In addition, there is another three-piece bathroom on the second floor with a free-standing bathtub. On the third floor are two bedrooms both overlooking the rear garden. There is excellent ceiling height in both bedrooms. From the east bedroom there is access to the rooftop that could be used as a terrace. The lower-level laundry room has a one-piece bathroom with a laundry sink, furnace and storage area. Nearby, are fabulous restaurants, amazing specialty shops, parks, and an easy stroll to the TTC. This special offering is often admired & offers a wonderful opportunity for those seeking one of the very few stone homes in Rosedale to customize to their own liking. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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40 Castle Frank Crescent in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12376693
40 Castle Frank Crescent Toronto M4W 3A3
$4,659,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12376693
- Bedrooms:
- 5
- Bathrooms:
- 5
OPORTUNITY IS KNOCKING! TOTAL SQUARE FOOTAGE JUST OVER 6600 Sq. Ft. Live On The QUIETER SIDE Of Castle Frank! An Incredible Opportunity Awaits In South Rosedale. One Of The Largest Lots Available In This Historic Neighbourhood For An Amazing Price. Time Will Not Wait For Such An Opportunity. Embrace The Chance To Own A Grand Piece Of History: Circa-1908 , Brimming With Charm And Character .Featuring Numerous Architectural Details And A Generous 110-Foot Frontage, This Stately Home Offers Exceptional Space And Elegance. With 4,848 Sq. Ft. Of Above-Grade Living Space Plus An Additional 1,800 Sq. Ft. In The Lower Level, There Is Plenty Room For Multigenerational Living Or Grand Entertaining .Step Inside To An Elegant Centre Hall , outstanding family room with Soaring barreled Ceilings And Massive Bay Windows That Flood The Home With Natural Light. This Home Also Features Three Fully Renovated Bathrooms, Including Two With Heated Floors, Ensuring Comfort And Style .While There Have Been Extensive Renovations, The Discerning Buyer May Wish To Bring Their Own Vision And Further Customize This Beautiful Home To Their Preferences. The Seller Also Has A Scavolini Kitchen Plan Available For The Buyer, Offering An Exciting Opportunity To Create A Dream Kitchen. Enjoy The Sensational Yard And Landscaped Grounds, Home To One Of The City's Oldest Japanese Maples. The Coach House/Garage Provides Perfect Storage Or The Potential To Convert To A Studio Space. Step Out Into Your Private Backyard Oasis, With Winding Pathways And Vibrant Perennials. This Home Offers Great Value Per Square Foot And Sits On A Solid 2-Foot-Thick Foundation Truly Built Like A Fortress. With Over 14,000 Sq. Ft. Of Lot Area, This Is An Exceptional Find. Don't Miss Your Chance To Own A Unique And Rare Piece Of South Rosedale History. A Must-See Check It Out And Seize This Opportunity! Homes Like This Do Not Come Up Often-Endless Options Here! More detailsListed by BOSLEY REAL ESTATE LTD.- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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68 Rowanwood Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12377059
68 Rowanwood Avenue Toronto M4W 1Y9
$7,499,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12377059
- 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- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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45 South Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12378216
45 South Drive Toronto M4W 1R3
$5,125,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12378216
- Bedrooms:
- 4
- Bathrooms:
- 4
An exquisite South Rosedale jewel where timeless architecture meets refined modern luxury. This exceptional Rosedale residence is truly a rare gem. Nestled in one of the neighbourhoods most coveted and picturesque enclaves, the home exudes understated elegance and superior craftsmanship. Every detail has been thoughtfully designed and is move-in ready. Superb principal rooms, including the formal living room with a stately fireplace and French doors that lead to the courtyard. The primary bedroom is a heavenly retreat with extensive closets and the sublime 5-piece ensuite. Bright and spacious additional bedrooms, and a luxurious wood panelled library. The finished lower level offers more beautiful and functional space. The homes layout is versatile and welcoming, offering generous space for entertaining or quiet retreat. The home boasts an abundance of natural light, enhanced by serene walled gardens creating an atmosphere of privacy and calm rarely found in the heart of the city. Additional features include a garage and private driveway, immaculate landscaping, and proximity to the best of the city: walk to Yonge/Bloor, the TTC subway, and top-tier schools including Branksome Hall around the corner. This property is undeniably special, much admired, and offers an elegant lifestyle. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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68 Astley Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12368140
68 Astley Avenue Toronto M4W 3B4
$2,795,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12368140
- 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- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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74 Dale Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12360231
74 Dale Avenue Toronto M4W 1K9
$3,995,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12360231
- Bedrooms:
- 6
- Bathrooms:
- 5
Absolutely Stunning Rare South Rosedale 5+1 Bed 4.5 Bath Fully Freehold Detached Home With Garage & With Permit for Secondary Unit Applied with City for Already Finished 1 Bedroom + 1 Bathroom Basement + Rec Room + Separate Laundry Suite With Separate Entrance, for Less than Half the Price of Condo Townhomes on the Street In Canada's Most Coveted Neighborhood With Proximity To Top-Ranked Schools; Elementary School*Rosedale Public*, High School *Northern Secondary*, Private Schools *Branksome Hall, Upper Canada College & The York School*, Recently Spent More Than $150K On Reno, Newer Hardwood Floor Throughout, 4 Newer Washrooms, Newer Roof, Brand New Dig Out Basement Concrete And Weeping, And Much More! 100 Meters To Castlefrank Subway Station! Excellent Location, Mins To DVP/Bloor/Gardiner, Yonge/Bloor, Danforth Food/Entertainment & Yorkville Shopping Districts. Close To UofT, Hospitals, Museums, Business & Entertainment Centres. More detailsListed by MINMAXX REALTY INC.- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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329 Glen Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12354265
329 Glen Road Toronto M4W 2X4 OPEN HOUSE: Sep 07, 202502:00 PM - 04:00 PM EDTOpen House on Sunday, September 7, 2025 2:00PM - 4:00PM
$1,979,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12354265
- Bedrooms:
- 1
- Bathrooms:
- 3
Welcome to the most unique opportunity in the best part of Toronto: Rosedale. Your chance to take advantage of a detached home on a 30X136 lot with a spectacular curated front and backyard including wood burning fireplace and 10 person hot tub and large composite deck. This home was custom designed by the seller for their lifestyle but can be re-imagined to suit your vision. Step inside and get a feel for the space and potential. Enjoy the Bali inspired décor! Home sold as is and with all furnishings. 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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88A Glen Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12330089
88A Glen Road Toronto M4W 2V6
$2,680,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12330089
- Bedrooms:
- 3
- Bathrooms:
- 4
Tucked into the leafy calm of South Rosedale, this stately brick home is a study in quiet luxury. Set on an exceptionally deep (187') tree-canopied lot, it offers approx. 2,800 sq. ft. of elegant, intuitive space over 3 levels- ready for a new owner's vision or to move in and enjoy! The side-centre hall plan opens with traditional confidence: a formal entry, finely scaled rooms, rich hardwood flrs, wrought iron rails & panel moulding add architectural depth. A gentle rhythm of East- & West-facing light flows through the home. The first of 2 powder rms is discreetly tucked off the main hall, while a convenient 2nd 'everyday' entrance from the garage leads to a mud/laundry rm & 2nd powder on the lower lvl. The formal dining rm connects to a classic kitchen w/ cream cabinetry, granite counters & Wolf range. A wide pass-through w/ breakfast bar bridges the two spaces, fostering easy flow between daily living & entertaining. French doors at either end extend the living area outdoors- East to a sun washed morning terrace, West to a secluded deck & garden framed by mature trees & perennial borders. Upstairs, 3 well-proportioned bdrms w/ bespoke built-ins enjoy tranquil green views. Two baths serve the upper lvl, including a 4-pc primary ensuite. The walk-out lower level features a large family rm w/ brick fireplace, 900-bottle wine cellar & walk-out garden access. A built-in garage w/ interior access, EV charger & private drive with parking for 3 cars completes the offering. All just mins to top-rated schools, beloved Summerhill Market, Rosedale subway, Craigleigh & Chorley Park, and the upscale boutiques, fine dining & cafes of Yonge St. & Yorkville. Minutes to DVP. Quick commute downtown via transit. Proof that tranquillity and connectivity can indeed go hand in hand. More detailsListed by SAGE REAL ESTATE LIMITED- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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10 Pine Hill Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12330644
10 Pine Hill Road Toronto M4W 1P6
$7,995,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12330644
- Bedrooms:
- 5
- Bathrooms:
- 5
Updated Rosedale Residence at Courts End. Fantastic Opportunity For Multi-Generational Use Or Partnership Living While Enjoying Two Primary Suites. Sited On A Sprawling Double Lot In Toronto's Most Prestigious Neighbourhood, A Rarity Both In Scale & Sophistication. Meticulously Preserved Victorian Architecture, Elevated W/ Modern Luxuries & Discerning Taste. Original Heirloom-Quality Millwork, Solid Wood Doors & Oak Floors Throughout. Enchanting Forested Backyard Among The Largest In The Neighbourhood. Impressive Entrance Hall W/ Marble Floors. Living Room W/ French Doors To Rear Gardens, Gas Fireplace W/ Stunning Sculptured Marble Surround. Formal Dining Room W/ 10-Ft. Ceilings & Original Crown Moulding. Charming Family Room W/ Custom-Built Brick Accent Wall, Classic Gas Fireplace & Wall-to-Wall Bookcase. Light-Filled Gourmet Kitchen W/ High-End Appliances, Central Island W/ Brazilian-Imported Stone Countertop, Custom Cabinetry, Breakfast Area & Walk-Out To Deck. Exquisite Office W/ 20+Ft. Vaulted Ceilings, Mezzanine Balcony & Gas Fireplace W/ Original Blue Marble Surround. Two Expansive Primary Suites On Second Floor. First Primary Suite Boasts Custom-Built Beauty Room, 5-Piece Ensuite W/ Solid Onyx Stone Finishes, Vast Private Boudoir & Dressing Room. Second Primary Suite W/ Bespoke Walk-In Closet & 5-Piece Ensuite W/ Marble Finishes. Third Floor Presents 2 Bedrooms, Sitting Room & 4-Piece Bathroom. Updated Basement Featuring Entertainment Room W/ Lounge & Custom-Built Wet Bar W/ Waterfall-Style Island, Nanny Suite, 3-Piece Bathroom W/ Heated Floors, Laundry & Mudroom W/ Garage Access. The Most Impressive Backyard On The Block W/ Tree-Lined Privacy, Garden Paths, Large Deck & Stone Waterfall. Sought-After Location On Quiet Cul-de-Sac, Steps To Branksome Hall, Rosedale Valley, Bloor-Yorkville, TTC & Downtown. A Truly Remarkable Residence In Every Aspect. More detailsListed by RE/MAX REALTRON BARRY COHEN HOMES INC.- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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37 St Andrews Gardens in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12324369
37 St Andrews Gardens Toronto M4W 2C9
$5,988,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12324369
- Bedrooms:
- 6
- Bathrooms:
- 5
Timeless Elegance Meets Family Luxury in North Rosedale - Welcome to an extraordinary residence in the heart of prestigious North Rosedale, where refined design, thoughtful functionality, and resort-style living come together in perfect harmony. From the moment you enter, this stunning family home captivates with its exquisite herringbone floors, elegant principal rooms, and seamless flow. A sophisticated main-floor office (currently a stylish music lounge), a generous dining room ideal for entertaining, and a breathtaking open-concept kitchen and family room offer the perfect blend of everyday comfort and elevated style. The magic continues outdoors. Step into a private backyard oasis designed for unforgettable moments. Enjoy the integrated hot tub, saltwater pool, pergola-covered lounge, outdoor TV, and an exceptional cabana complete with bar fridge, flat-screen TV, and sauna. This is outdoor living at its absolute finest. The lower level offers a full nanny or teen suite, a cozy lounge, creative play/art space, and a state-of-the-art home gym. The serene primary suite is a retreat of its own, featuring a luxurious en-suite, walk-in closet, and private walk-out balcony overlooking the gardens. With five spacious bedrooms, versatile living spaces, and an unbeatable location steps to Rosedale Park & the boutique offerings of Summerhill, this residence presents a rare opportunity to own one of the most coveted addresses in Toronto. A home where elegance meets ease & every detail is simply exceptional. More detailsListed by RE/MAX PREMIER THE OP TEAM- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
Data was last updated September 7, 2025 at 03:15 PM (UTC)
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