Homes for Sale in Rosedale Toronto Canada
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40 Castle Frank Crescent in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12111168
40 Castle Frank Crescent Toronto M4W 3A3 
$4,695,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12111168
- Bedrooms:
- 5
- Bathrooms:
- 5
OPORTUNITY IS KNOCKING ! 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: this circa-1908 home is 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 with soaring curved 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. Dont 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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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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74 Dale Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12330835
74 Dale Avenue Toronto M4W 1K9
$2,790,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12330835
- 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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20 Elm Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12300699
20 Elm Avenue Toronto M4W 1N3
$13,950,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12300699
- Bedrooms:
- 6
- Bathrooms:
- 9
A magnificent and grand Rosedale estate that seamlessly blends modern, state-of-the-art living with historic charm. Set on an extraordinary 80 x 229-foot lot - spanning over 1/3 of an acre - this meticulously restored home offers over 11,500 sq ft of living space across four levels. This elegant residence showcases original architectural flourishes, including hand-carved moldings, eight fireplaces, and a dramatic entrance foyer. Soaring ceilings and intricate details throughout preserve the homes 1890 heritage while incorporating every modern luxury. The home features a huge gourmet kitchen, three outstanding family living areas, spa-inspired bathrooms, and an expansive four-room primary suite. A four-floor elevator ensures effortless access to every level. The backyard is a private urban oasis framed by manicured gardens and offering a magnificent pool and spa, along with multiple terraced patios for entertaining. A gated driveway leads to a detached three-car garage, with parking for up to nine vehicles. Located within walking distance to the TTC subway, top private and public schools, and with quick access to major routes and downtown, this is an unmatched opportunity. A rare chance to own a landmark Rosedale property perfect for grand entertaining and refined daily living. Truly for the most discerning buyer. 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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57 Castle Frank Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12207133
57 Castle Frank Road Toronto M4W 2Z5
$3,499,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12207133
- Bedrooms:
- 5
- Bathrooms:
- 4
SLAY THE DRAGON AND LIVE AT CASTLE FRANK! Hold onto your hearts Rosedale: Gorgeous 1914 Craftsman with sweeping views over the gates of Drumsnab Park. With presence and poise, this home introduces itself before you even step inside through its deep front veranda that feels straight out of a fairytale among the lush and mature trees of South Rosedale. All four finished levels are elegant, expansive, and kissed with soft, natural light through many period specific leaded windows. Main floor with large principal rooms, wood burning fireplace, fabulous wainscotting and many cozy vignettes for reading and lounging. Bedroom suites upstairs are absolute sanctuaries with ample room for oversized beds, lounging, late-night chats and never wanting to leave. Finished basement with fabulous sunk-in media room and extra suite for guests, live-in help or independent teenager. Super rare and ultra private garage/parking.Minutes walk to the subway station, Craigleigh Gardens, the DVP and the Danforth. Perfect location for Rosedale Public and Branksome Hall schools.Commanding from the curb, graceful at every turn. The type of family home that makes you want to host every holiday and be part of a garden club. #letsbefrank #youneedacastle #sameherereally More detailsListed by SAGE REAL ESTATE LIMITED- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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11 Hawthorn Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12287948
11 Hawthorn Avenue Toronto M4W 2Z1
$4,498,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12287948
- Bedrooms:
- 4
- Bathrooms:
- 5
Nestled in prime South Rosedale & featured in 'Style at Home' Magazine this stunning 4BR plus office,5-bathroom family home sits on a rare 35 by 150-foot pool size lot & offers over 3800 sqft of elegant living space incl LL. With gorgeous curb appeal on one of Rosedale's most a sought-after family-friendly streets, this residence blends timeless charm with modern luxury. The welcoming front foyer features a beautifully appointed 2-piece bathroom, with rich oak hardwood floors extending throughout the home. The open-concept living & dining area boasts bay windows, a wood-burning fireplace, exquisite leaded glass windows, and custom built-in bookcases. A spectacular walnut chef's kitchen serves as the heart of the home, featuring a long breakfast island, marble countertops, a Butler's pantry and an open flow to a cozy sitting area and breakfast nook overlooking the private deep backyard oasis, perfect for entertaining. A convenient & functional mudroom with built-in closets provides direct access to the outdoors. The 2nd floor offers a luxurious and spacious primary bedroom with large sitting area, brand new ensuite bathroom, bay windows, & ample storage. A bright 2nd bedroom features an artisan tin ceiling, while a light-filled office includes wraparound windows & a built-in walnut entertainment unit overlooking the backyard. A charming sitting area on 2nd floor landing perfect for a reading nook, & a brand new two-piece bathroom complete this level. The 3rd floor has 2 beautiful bedrooms, both with broadloom, large windows, closets, & LED lighting. A luxurious 4-piece bathroom features marble finishes & heated floors. The finished basement offers heated floors, built-in speakers, a spacious laundry room, abundant storage, & a large rec room-perfect for family activities or entertaining. Located in one of Toronto's most prestigious neighborhoods, this home is close to the TTC, DVP, downtown, and top-rated schools, including Branksome Hall and Rosedale Public School. 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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45 South Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12125446
45 South Drive Toronto M4W 1R3
$5,475,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12125446
- 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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33 Rosedale Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12108186
33 Rosedale Road Toronto M4W 2P5
$6,690,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12108186
- Bedrooms:
- 5
- Bathrooms:
- 5
One of kind contemporary detached house in 50.5 x 352.69 feet premium lot offers amidst Ravine with mature tree vistas in prime south Rosedale. This house has a very cool interior layout and is infused with an abundance of natural lights. Very spacious 5 bedrooms, 6 washrooms; 2 car garages, 2 driveway parking spots and additional 2 carport parking spots. This beautiful quiet residence in the Heart of downtown Toronto only 7 min walk to Rosedale Subway station, easy walk to Yonge Bloor Shops, 25 Min walk to U of Toronto, transit to Metropolitan University (TMU), 7 min to Hwy 404 etc. Upon entering, there is an inviting sunken living room overlooking spaces in dining room, These rooms have the advantage of endless view of the lush green and beautiful Ravine! Kitchen has both Gas & Electric Stove; Centre island has fruit sink. There are numerous walk-out to decks. The self-contained master room has sitting room; dressing rooms. The lower level enjoy an indoor pool, washrooms, great room. More detailsListed by HOMELIFE BROADWAY REALTY INC.- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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52 Rosedale Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12160493
52 Rosedale Road Toronto M4W 2P6
$9,980,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12160493
- Bedrooms:
- 6
- Bathrooms:
- 7
This majestic Neo-Georgian home sits proudly on the best block in all of the coveted south west Rosedale. This serene & peaceful pocket is ironically steps to all the fabulous shops & restaurants on Yonge St. Your children can conveniently walk to Branksome & York school. The York Club & Toronto Lawn are also just minutes away. The joy & convenience that come with living in this coveted enclave cannot be overstated. Beyond the striking & stately facade, 52 Rosedale Rd. transports you to the earliest days in Rosedale, where the grand mansions with their elegantly proportioned rooms & tall ceilings were home to Toronto's founders. It was in these rooms where Toronto's elite raised their families, broke bread & forged the future of this city. From the beautiful chef's kitchen w/cozy eat in area, to the grand dining area, one can host extravagant dinner parties, the oversized living area is the perfect backdrop for unwinding day to day, & hosting fabulous cocktail parties. All of these impeccable spaces overlook the superb gardens that sit peacefully behind the tall garden wall, ensuring tranquility & privacy. The large sunken den area with tall & deep coffered ceilings is an absolute delight. The 2nd floor houses 2 accessory bedrooms, each w/ensuite baths & the primary bedroom sanctuary. This expansive space boasts his & hers closets & bathrooms & a private office that provides a quiet workspace. The 3rd floor houses 2 additional bedrooms & an oversized room perfect for a home gym or recreational space for children. Walk out to your private sun deck, tan & enjoy breathtaking views of the Toronto skyline. The lower level boasts great ceiling height throughout, the large rec area is the perfect space for kids of all ages. 52 Rosedale Rd. offers best in class parking, with a full 2 car garage with direct access to the home, 2 additional spaces in front of the garage & a stately circular drive that can easily carry 3 more cars. 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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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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91 Glen Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12286583
91 Glen Road Toronto M4W 2V5
$3,350,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12286583
- Bedrooms:
- 3
- Bathrooms:
- 4
Exuding timeless elegance, this South Rosedale townhome was designed by renowned custom homebuilder Joe Brennan. Nestled on a winding, tree-lined section of Glen Road with a long setback from the road to ensure privacy. With over 3,300 sq ft across three levels, this home offers a seamless layout with the opportunity to customize as needed. The main floor of this home is truly a 'wow' - oversize in scale with high ceilings and well-suited for entertaining. Featuring magnificent natural light cascading from multiple skylights, rich dark hardwood flooring and a wood-burning fireplace flanked by large picture windows overlooking the garden. The formal dining room comfortably seats eight to ten people and features beautiful panelling and a convenient servery leading to the thoughtfully-designed kitchen. On the second floor, the massive primary bedroom offers a bright and airy ensuite with skylight, and the spacious second bedroom has its own ensuite and a walk-in closet. Ample space on the second floor offers the possibility to reconfigure for three bedrooms. The above-grade ground level offers a family room / office with a gas fireplace, large picture windows and a walk-out to the garden. Truly an enviable location, access to Craigleigh Gardens park and Milkmans Lane trail is just around the corner for a peaceful retreat under the tree canopy. Toronto's finest private and public schools including Branksome Hall and Rosedale Jr Public School are nearby. Situated just steps to the bus stop and walking distance to both Rosedale and Castle Frank subway stations ensures that you are well connected to the city. Rare three-car parking with an integrated garage providing direct access to the home and a long private interlocking brick drive. This is a wonderful opportunity for discerning buyers seeking the lifestyle and tranquility of this coveted neighbourhood. 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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97 Glen Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12305140
97 Glen Road Toronto M4W 2V5
$8,900,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12305140
- Bedrooms:
- 7
- Bathrooms:
- 9
A Rare chance in one of the most celebrated neighbourhoods, South Rosedale. Perfectly set back from the main street for privacy, this spectacular oversized lot offers expansive outdoor space upon it's impressive entrance. This is a once-in-a-generation opportunity. Grand, one-of-a-kind estate home in the heart of Toronto's most distinguished neighbourhood. A true Rosedale landmark with historical significance, this magnificent residence exudes timeless sophistication and sits on a prized street with other elegant homes and estates. With a presence like no other, it offers an unmatched blend of heritage, scale, and distinction. Boasting over 8,000 square feet of planned living space, this exceptional property offers unrivaled architectural elegance. Currently under renovation and being sold *as-is*, the home includes approved permits and meticulously designed architectural plans. The plan is a beautiful, timeless vision blending classic traditional design with refined modern touches. A plan that took years to perfect, it offers the ideal balance of elegance, functionality, and lasting appeal. It's grand dedicated spaces and stately proportions will surely satisfy the most discerning taste. This is a home meant for a growing, multi-generational family designed to be cherished and lived in for generations to come. Live surrounded by the best of Toronto just minutes to top private schools, ravines, Yorkville, and the downtown core while enjoying the peaceful charm and exclusivity of one of the city's most celebrated enclaves. Do not miss this legacy in the making. **photos are renderings** 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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135 Crescent Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12224644
135 Crescent Road Toronto M4W 1T8
$9,995,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12224644
- Bedrooms:
- 7
- Bathrooms:
- 6
"Horsman Hall" Is A South Rosedale Landmark, And Truly A Rare Offering. The Architecturally Significant Main House Fronts Onto A Semi-Private Road And Has Been Meticulously Restored & Fully Renovated To Expand The Living Area To 5,515Sf. The Main Floor, Graced W/Herringbone Patterned European White Oak Hardwood Flooring & Tiles In An Elegant Palette, Features An Open Living & Dining Room W/Bar Area & Wine Fridge, And A Private Library. The Large Kitchen Features A Centre Island, Separate Floating Eat-In Counter, And Is Open To The Family Room W/Sweeping South & West Views Of The Garden & Coach House From The Floor To Ceiling Windows. The Original Leaded Glass Has Been Preserved & Supplemented W/New Large Format Windows. Dramatic, Sun Drenched, Main Staircase. Roof Top Deck W/Views Of Downtown. The Impressive, Light Filled, Lower Level Has Been Selectively Lowered, Finished With Polished Concrete Floors & Includes A Rec. Rm. W/Surround Sound, Wet Bar, Illuminated Glass Wine Display, Home Gym & Bdrm. W/Ens. The Long Gated Driveway Leads You To A Rare Separate 1,900Sf 2-Storey Coach House W/Elevator & 2 Bdrms, Courtyard, Outdoor Cooking Area, & A Muskoka-Inspired 2 Car Garage With EV Rough-In! Steps To Yorkville, Parks, Ravines & Schools. 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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18 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12179224
18 Chestnut Park Road Toronto M4W 1W6
$15,198,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12179224
- Bedrooms:
- 6
- Bathrooms:
- 7
Located in the prestigious Rosedale neighbourhood, this architectural masterpiece sits on one of the finest streets where there are no visible power lines and no through traffic, as it is comprised of 3 crescent shaped roads. Enjoy a custom architectural steel floating staircase which brings light through the third-floor skylight to lower level wine cellar with a glass ceiling. The finishes are extraordinary, and the layouts on every level are perfect for a family life as well as entertaining. Every bedroom has an en-suite bathroom. The lower level mirrors the luxury above with a fitted bar, 2 storey wine cellar, a billiard room, an exercise room, and a sunken golf simulator. The structure is also in place for the installation of an elevator. What is truly unmatched is the 3-car circular drive as well as a separate coach house with living space above and a double or triple car garage below. Steps to the Rosedale subway and Yonge St. shops. This home is an opportunity to live in true, unsurpassed turnkey luxury. 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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11 Beaumont Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C9366330
11 Beaumont Road Toronto M4W 1V4
$17,800,000Residential Freehold- Status:
- Active
- MLS® Num:
- C9366330
- Bedrooms:
- 4
- Bathrooms:
- 4
Rare opportunity to own one of the citys most iconic properties, nestled into the side of the Rosedale ravine. This magical home is impossible to replicate originally designed by internationally acclaimed architect Eb Zeidler (of Eaton Centre fame) & completely rebuilt and reimagined by Peter Clewes (Architects-Alliance). The result: a modern, minimalist masterpiece that juxtaposes the heritage façade w/ a striking glass cube to blend seamlessly w/ nature. Deceptively discreet, this majestic home opens to 7,000+ sqft of living space. Set on 1 ACRE+ of land w/ a ~175x313 ft south-facing lot & sweeping skyline views, it offers a level of privacy rarely found in the city. The property to the East w/ ~1 ACRE of land is owned by the Ravine Conservation Authority ensuring absolute tranquility & nature. Custom landscaping w/ native species creates breathtaking outdoor views, while professionally designed lighting makes the property glow from sunset to nightfall. Watch deer, bunnies & owls become part of the scenery in your own private sanctuary. Inside, impeccable finishes shine from the sleek Poliform kitchen to the UT glass elevator. Every rm has been carefully considered, with flowing transitions & soaring ceilings that allow daylight to flood in from all sides. No unsightly posts or pillars here this steel-structured hm was built at a commercial level to preserve every clean line and open view. Featuring 4 bdrms, a massive great rm, and a kitchen/dining/sitting rm perfect for both grand entertaining & intimate family living. The primary suite stuns w/ E, W & S exposures & a showstopping ceiling detail. A resort-style pool is framed by expansive decks ideal for lavish parties, while terraced steps lead to a half tennis court ready to be reimagined as a pickleball court or play space. Just minutes to top private schools, restaurants & clubs, 11 Beaumont is a one-of-a-kind estate in the heart of the city. 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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82 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12178239
82 Chestnut Park Road Toronto M4W 2R3
$14,250,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12178239
- Bedrooms:
- 5
- Bathrooms:
- 6
Endless Summer in a Poolside Paradise with 7-Star Resort-Style Luxury! Experience the ultimate retreat in the highly sought-after Rosedale neighborhood, west of Mt. Pleasant. This expansive 85-foot-wide tableland property sits atop the exclusive Chestnut Park ravine, overlooking serene parkland below. A true garden oasis, the stunning oversized pool is virtually irreplaceable in this area, creating an idyllic opportunity for a captivating & private escape. 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 home features stunning multiple terraces for sitting, dining, and entertaining, complete with an outdoor kitchen. Inside, discover serene, curated interiors & an exceptionally sumptuous primary suite with his & her separate dressing rooms. This trophy property blends timeless grace, alluring charm, & unparalleled privacy with the convenience of everyday luxury in a prized neighborhood. Additional highlights include an ELEVATOR, generator, garage with lift, & ensuite bathrooms in all bedrooms. Set beneath a lush, treed canopy, you are just steps from the subway, top private & public schools, premier shopping, area parks, tennis, skating & hiking & biking trails extending to the lake. Plus, Yorkville & the city center are only a 10-minute drive away. 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 Rowanwood Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12094739
68 Rowanwood Avenue Toronto M4W 1Y9
$7,499,000Residential 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- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
-
52 Roxborough Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12317307
52 Roxborough Drive Toronto M4W 1X1
$7,800,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12317307
- Bedrooms:
- 4
- Bathrooms:
- 5
Set along one of North Rosedales most established and tree-lined streets, this reimagined home offers a rare combination of architectural integrity and modern refinement. The 128-foot frontage provides a sense of space not often found in the city, while inside, the layout unfolds with ease and intention. Natural light fills the main level, where principal rooms overlook a quiet, green backdrop. The kitchen, designed for everyday living as much as entertaining, opens into a warm, inviting family space with seamless access to the private and ravine-like backyard. Upstairs, four well-proportioned bedrooms offer privacy and flexibility. The primary suite is tucked away, with a generous walk-in closet and a spa inspired ensuite that brings a sense of calm. A secondary suite with its own balcony is perfect for extended family or guests, and two additional bedrooms are thoughtfully connected by a shared bath.The lower level is bright and functional, with an above-grade design that welcomes natural light. It features a spacious laundry room with direct garage access and a flexible open layout, ideal for a home gym, media lounge, office, or guest suite. Whether for extended family, work-from-home needs, or future adaptability, this level offers space that evolves with your lifestyle. A heated driveway and walkway lead to an attached garage, plus two-car parking on the driveway for car enthusiasts or additional guests. A short walk to Chorley Park, the Brick Works, and Summerhill Market, and situated near some of the citys top schools. More detailsListed by FOREST HILL REAL ESTATE INC. and THE AGENCY- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
-
56 Roxborough Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12138839
56 Roxborough Drive Toronto M4W 1X1
$4,900,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12138839
- 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- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
-
45 Mathersfield Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12272916
45 Mathersfield Drive Toronto M4W 3W4
$5,899,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12272916
- Bedrooms:
- 5
- Bathrooms:
- 6
Luxury meets location. South Rosedale home would be considered a prize in this uniquely located, small development completed roughly 25 years ago. The quality of construction combined with custom moldings, and vaulted ceilings states luxury. The convenience of being able to walk to top restaurants, shopping, and the Summerhill subway in under 5 minutes states location. More detailsListed by KELLER WILLIAMS REFERRED URBAN REALTY- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
Data was last updated August 12, 2025 at 06:15 AM (UTC)
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