Originally designed in 1908 by celebrated architect Eden Smith, this Rosedale landmark has been brilliantly reimagined and meticulously renovated to the highest standards. With over 8,900 sq.ft. of living space, the home blends classic architectural charm with sophisticated modern design, creating a rare opportunity in one of Toronto's most coveted neighbourhoods. Set on a deep ravine lot, the property has been reinforced to protect against erosion and offers stone stair access directly to the extensive ravine trail system a private escape into nature, all while being just steps to Yonge Street, the TTC, shops, and fine dining. Inside, the home is both grand and welcoming, featuring 6+1 bedrooms, 6 bathrooms, and a private office plus a second floor family room, perfectly suited for large scale family living and entertaining. The Chefs kitchen is a showpiece, designed with two oversized islands, heated floors, a breakfast area, dual ovens (including steam), and dual dishwashers one full-size and one drawer making it both highly functional and beautifully designed. A centrally located glass-doored elevator with custom metal paneling connects all levels, complementing the homes graceful flow. The lower level is exceptionally finished, with soaring 9'6" ceilings, radiant heated tile floors in the newer section, a dedicated gym area, naturally climate controlled wine storage, a walk-in cedar closet plus a second oversized closet, and even a full second kitchen for extended family, staff, or entertaining on a grand scale. Throughout, every element has been carefully considered bespoke millwork, curated materials, and architectural details that preserve the homes character while adding contemporary luxury. This is more than a residence: it is a true Rosedale dame offered for the first time in over 20 years, updated for modern living, ready to be enjoyed for generations to come.More details
Listed by ROYAL LEPAGE REAL ESTATE SERVICES OXLEY REAL ESTATE
Perfectly situated on an estate-lined street, in the heart of Rosedale - Toronto's most storied & sought-after enclave-this impressive luxury showpiece excites with its creative sophistication & inspired modern liveability. Set on a magnificent & rare 100'x150' double lot, the property is a tour-de-force of landscape design featuring stone walkways leading to 3 enchanting outdoor zones: a covered loggia beside a sculptured waterfall, stone terraces with multiple seating & dining areas, & a stg pavilion; a manicured, flower bordered central lawn; & a private, tree-screened sports court. Mature cedars & towering foliage embrace the property, providing exceptional privacy. This sun-lit sanctuary may well be one of the most beautiful & extraordinary gardens in Rosedale. Custom built in 2003, the home's striking classical stone façade reflects rigorous architectural integrity & perfect symmetry where the fine craftsmanship & quality materials embrace the enduring charm of traditional Rosedale. It is a home designed to open up and share! Inside, alluring elegance & cocooning ease beguile. Entertaining is a dream in the dramatically proportioned entrance hall & generously scaled principal rooms, featuring French doors & windows, rich millwork & detailed mouldings. Sprawling & relaxed living bedazzles in the family areas where the beamed Muskoka style, 2-storey Great Room anchored by a massive open hearth fireplace, leads effortlessly to the unparalleled open-concept Family, Dining, Sitting areas & spectacular chef's kitchen. Boasting a huge centre island, stone countertops & top-tier appliances, the well ordered, bespoke kitchen infuses all with captivating warmth, spirited refinement & glamorous functionality, making lavish parties a breeze here. Soaring ceilings & walls of windows allow the light to flood in from all sides of the formal & intimate family rooms. Upstairs, the expansive primary suite is a haven of tranquility, with it's serene sitting bay & walk-out deck.More details
Rosedale - Toronto's Most Prestigious And Storied Neighbourhoods. Awe-Inspiring 2017 Renovation Of The Highest Standards, This Three-Storey Estate Of 8,881 Sf Plus Its Amenity Rich Lower Level Is Nestled On Over 108' Of Stunning Frontage. Old-World Architecture With A Contemporary Twist. Step Inside To Discover Generously Proportioned Principal Rooms, Soaring Ceilings, Sweeping Grand Staircase And An Effortless Flow Ideal For Both Intimate Family Living And Large-Scale Entertaining. Heated Stone Floors Run Throughout Offering Year-Round Comfort.The Heart Of The Home Is A Chefs Dream Kitchen With Top Of Line Appliances And Seamless Indoor-Outdoor Connection. All Bedrooms With Private Ensuites, Primary Retreat Boasts 6pc Marble Bath, Opulent Boudoir And Dedicated Laundry Facilities. 3rd Storey Is Enhanced With Two Additional Bedrooms Each With Ensuites, Private Kitchenette And Open Sitting Area. The Lower Level Completes This Masterpiece With An Oversized Wine Cellar, Games Room/Media Room, Private Sleeping Quarters And Full Spa With Exercise Room, Indoor Pool Swim Spa And Steam Shower. Outside, Enjoy Lush Professional Landscaping, Unparalleled Privacy And Serenity In The Heart Of The City. A Stunning Concrete Pool With Built-In Hot Tub, A Fully Equipped Outdoor Kitchen. Multiple Seating Areas Perfect For Entertaining Or Serene Relaxation. Rare 3 Gar Heated Garage With Ev Charger. Enjoy The Best Of Urban Living With Close Proximity To Yorkville, Downtown Core, Public Transit, And Torontos Top-Ranked Elite Public And Private Schools. This Is A Once-In-A-Lifetime Opportunity To Own A Landmark Home In One Of The City's Most Coveted Enclaves.More details
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 facade 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 details
Listed by ROYAL LEPAGE REAL ESTATE SERVICES OXLEY REAL ESTATE
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 details
Nestled in one of Toronto's most coveted neighbourhoods, 170 Roxborough Drive stands as a testament to timeless elegance and architectural brilliance. This landmark heritage house in North Rosedale offers an unparalleled blend of history, luxury, and modern living, seamlessly woven together to create a residence that is both sophisticated and welcoming. With its impressive stone walls and meticulously designed interiors by Robert Noakes, this home is a true gem in the heart of the city, offering the utmost privacy and exclusivity. Located just moments away from Chorley Park and the vibrant Summerhill Market this home enjoys the perfect balance of quiet residential living. The expansive property boasts 120 feet of frontage, surrounded by mature trees and landscaping, ensuring complete privacy while remaining close to the pulse of the city. The substantial stonework of this landmark house reflects the craftsmanship and care that has gone into preserving its historic charm, while modern updates ensure that the home is not only beautiful but also highly functional for contemporary living. The main floor of this remarkable home offers an array of grand principal rooms that are perfect for both intimate gatherings and large-scale entertaining. With 5 generously sized bedrooms, each complemented with its own ensuite bathroom ensuring privacy, the primary bedroom is a sanctuary with 2 full bathrooms. The third level living room is a private retreat flanked by two bedrooms. Step outside into the beautifully landscaped garden where a stunning inground pool takes centre stage. Surrounded by flag stoned terraces and greenery this outdoor oasis with a built-in BBQ, is a peaceful and luxurious retreat. The focal point of the lower level is the temperature controlled wine cellar along with a media room, billiard room, and recreation room. A direct entrance from the two car garage and a walk out to the pool storage area and garden from this level are an added benefit.More details
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 Applegate 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. Applegate 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 timeless charm.More details
An unbelievable, unique opportunity to achieve your great architectural ambition, to create your own dream home on one of the most prestigious blocks in Canada. This iconic Rosedale residence set on a massive ravine lot (88 x 408 ft), only a handful of properties at this scale exist. With groundbreaking approvals to redefine the property that allow you to add a swimming pool, and create a garden oasis with ravine views in Rosedale's most coveted location. Approvals in place for pool and relocation of garage and driveway to create an expansive backyard. The stately home has over 5,000 sq ft above ground and 2,300+ sq ft on the lower level, all of which feature timeless architectural and design elements, including the stunning hand-crafted staircase, multiple original fireplaces, and intricate woodwork. With an enviable primary suite with attached private office, multiple walk-in closets, and an ensuite. Four more well-proportioned bedrooms are found on the second floor. This home can become the perfect narrative for your fabulous life.More details
What makes a property truly rare? At 139 Hudson Drive, it is not just the classic architecture or the breathtaking ravine setting, it is the scale and flexibility of what is possible. Whether you are dreaming of a legacy estate, envisioning a transformative new build, or simply seeking extraordinary land value in a premier neighbourhood, this is a once-in-a-generation opportunity. On this expansive, combined parcel, the only limit is imagination. Set across a sprawling 156 x 263 foot ravine lot, this property unites 139, 135, and 133 Hudson Drive into a single, grand holding. The home itself is set on the northernmost edge, with 75 feet of frontage at 139 Hudson Drive, overlooking the attached lots at 135 Hudson and 133 Hudson, offering an additional 80 feet of frontage for the total of 156 ft. The home offers a classic centre-hall design, refined architectural details, and an elegant indoor-outdoor connection to nature, with five bedrooms, four bathrooms, and beautifully maintained interiors rich with charm and craftsmanship. Surrounded by landscaped gardens, the home is thoughtfully designed for both everyday living and special gatherings, offering privacy and warmth in one of Toronto's most coveted neighbourhoods. Beyond the classic home currently perched on this incredible lot, the true potential of this property lies in the vastness of its land, three severed prime ravine lots offering endless possibilities. Whether maintained as an exquisite estate, renovated to expand the current home, or developed as one sees fit, the opportunity is as rare as it is flexible. With direct ravine access, multiple building options, and proximity to top schools, shopping, and transit, this land presents a rare offering for families, developers, or investors seeking scale, serenity, and prestige in a premier Toronto community.More details
Listed by ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM
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 details
An architectural tour de force by acclaimed Robert Le Blond, recipient of the 1990 Governor Generals Award in Architecture ("Head-Smashed-In Buffalo Jump" in Alberta, now a UNESCO World Heritage Site), this 20-year-young bespoke residence is a French Art Deco masterwork of craftsmanship with inspired ironwork by Goudy from Spain. Offering over 5,000 sq ft of living space on a coveted corner by Chorley Park in prestigious Rosedale, the home is clad in rare Manitoba Tyndall stone, prized for its striking fossilized patterning. The residence blends enduring elegance with modern comfort, from the heated front porch and rear veranda to the soaring 17-foot living room crowned by a vintage theatre chandelier and wrapped in rich, mahogany-stained Jatoba wood wainscoting and floors. Formal entertaining spaces flow seamlessly into the chefs kitchen, breakfast area, and family room, all opening onto a landscaped garden sanctuary. The detached, heated garage, complete with a skylight, wet bar, shower, and custom storage, offers versatility as a private workshop, while a gated driveway ensures both privacy and grandeur. With five bedrooms, two offices, five fireplaces, six bathrooms, wrap-around balcony and even a dedicated pet wash, every element reflects a commitment to refined living without compromise.More details
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 details
Data was last updated November 15, 2025 at 09:15 PM (UTC)
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