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
Located In The Heart Of Rosedale, One Of Toronto's Most Prestigious And Historic Neighbourhoods. This Extraordinary Estate Blends Timeless Architecture With Refined Contemporary Design. Set On Over 108 Feet Of Magnificent Frontage. Approximately 8,881 Square Feet Of Luxurious Living Space Plus A Spectacular Amenity-Filled Lower Level. A Breathtaking 2017 Renovation Elevated The Home To The Highest Standards Of Craftsmanship And Design. Grand Principal Rooms, Soaring Ceilings, And A Dramatic Sweeping Staircase Create An Unforgettable First Impression. Heated Stone Floors Throughout Provide Exceptional Year-Round Comfort. At The Heart Of The Home Is A Stunning Chef's Kitchen Appointed With Top-Tier Appliances And Designed To Seamlessly Connect Indoor And Outdoor Living Spaces. Each Bedroom Features Its Own Private Ensuite. The Luxurious Primary Retreat Offers A Magnificent Six-Piece Marble Ensuite, An Elegant Boudoir, And Its Own Dedicated Laundry. The Third Level Adds Two Additional Ensuite Bedrooms, A Private Kitchenette, And A Comfortable Sitting Area-Perfect For Guests Or Extended Family. The Exceptional Lower Level Rivals The Finest Private Clubs, Featuring An Oversized Wine Cellar, Games And Media Rooms, Private Guest Quarters, And A Full Spa Retreat Complete With Exercise Room, Indoor Swim Spa, And Steam Shower. The Beautifully Landscaped Grounds Provide Remarkable Privacy And Tranquility In The Heart Of The City. Outdoor Living Is Elevated With A Stunning Concrete Pool And Integrated Hot Tub, A Fully Equipped Outdoor Kitchen, And Multiple Seating Areas Ideal For Entertaining Or Quiet Relaxation. Rare Three-Car Heated Garage With EV Charger. Moments From Yorkville, The Downtown Core, Transit, And Some Of Toronto's Top-Ranked Public And Private Schools, This Remarkable Residence Represents A Rare Opportunity To Own A Landmark Home In One Of The City's Most Coveted Enclaves.More details
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 flagstone 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
Set on an extraordinary 300' deep ravine lot with remarkable table land in coveted South Rosedale, this distinguished residence offers timeless elegance, exceptional privacy and refined living surrounded by lush natural beauty. This home is so rare, as a recently built new home in this historically protected neighbourhood it is a true unicorn. Brilliantly designed with grand principal rooms, soaring ceilings and exquisite architectural details and huge scale this home blends classic contemporary character with modern comfort. Beyond generous expansive windows and French doors flood the home with natural light while breaking the barrier between inside and out. Your life is lived without restraint, fabricating seamless transitions to tranquil outdoor gardens, a magnificent terrace and beyond. Generous bedroom accommodations include a luxurious primary retreat with dressing area, complemented by versatile upper level spaces ideal for family living, work or guests. A fully finished lower level with walk-out provides outstanding recreation and entertaining areas along with additional living quarters, wine cellar and gym. Perfectly located, just moments to the best private and public schools, dining and shops along Rosedale high street and Yorkville, this is indeed a rare offering in Canada's best neighbourhood.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 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 opportunity to own a beautifully renovated character home in the heart of Rosedale. This elegant residence offers flawless design, luxurious amenities and every comfort imaginable. Set behind lush landscaping, the home offers striking street presence with a quiet confidence that immediately captures attention. This meticulously maintained home features four plus one bedrooms and seven beautifully designed bathrooms that are complemented by a craftsmanship rarely found. The chef's kitchen is both functional and elegant, featuring a Miele cooktop, Sub-Zero refrigeration, an eat-in area, and a walk-out to an expansive patio. A servery adds thoughtful storage and effortless entertaining appeal. A cozy yet connected family room flows seamlessly into the kitchen. spectacular living room has floor to ceiling glass doors that invite an abundance of light while creating seamless connection between indoor and outdoor living space. This wonderful formal entertainment space flows seamlessly between the living and dining room. The grand dining room offers an impressive setting for formal gatherings and special occasions. The expansive primary bedroom is a true retreat, offering generous space and thoughtful design. A private sitting area provides the perfect spot to unwind with a book or morning coffee while the adjoining dressing room adds a touch of luxury with ample storage space and boutique style organization. The second floor has two additional bedrooms and two bathrooms. The third floor suite has an expansive bedroom, desk, three piece bathroom, walk in closet and plenty of extra room for a seating area. The lower level is complete with heated floor, a media room with wet bar, spa bathroom and sauna. An elevator servicing all floors of the home. Detached two car garage, two additional parking spots, heated walkways and a beautifully landscaped yard. Truly a one of kind Rosedale home.More details
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. 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. 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. More than meets the eye, deceptively large rear garden offers an abundance of space for outdoor enjoyment including a plunge pool, if so desired. 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
Rare opportunity to restore a distinguished historic Rosedale residence to its original architectural integrity & create a bespoke home of exceptional grace & distinction, ideally positioned on one of Rosedale's most admired & private streets. Set on a wooded ravine-adjacent property surrounded by mature trees & prestigious estate homes, this residence offers a tranquil & picturesque setting that seamlessly blends privacy, prestige, & enduring connection to nature. The natural ravine backdrop provides year-round beauty & sense of retreat rarely found so close to the city's core. Classic proportions & refined period details define the home, including original hardwood floors, soaring ceilings, hand-carved mantlepieces, elaborate plaster crown mouldings, & a richly paneled library that reflects timeless craftsmanship. Grand principal rooms & elegant floor plan create exceptional flow & present rare canvas for thoughtful restoration & modern luxury. Location is equally compelling. Chorley Park & Craigleigh Gardens offer scenic hiking, jogging, & cycling trails that lead directly to the Evergreen Brick Works & connect to the extensive Don Valley park system. Nearby Rosedale Park & Ramsden Park provide tennis courts, skating rinks, & wading pools, while Mooredale House is a popular community centre. Summerhill Market, & fine shopping, dining, & upscale boutiques are found along the vibrant Yonge Street corridor. Public transit is readily available Motorists enjoy quick access to the Don Valley & downtown financial district. Some of Toronto's finest public & private schools are within walking distance or easily accessible by transit. Celebrated as one of the city's most prestigious neighbourhoods, Rosedale is renowned for its preserved architectural heritage, natural beauty, & exceptional quality of life. 7 Beaumont Road awaits the discerning buyer with vision-one who values history, artistry, and the enduring beauty of classical architecture. Photos virtually staged.More details
Originally a stately classic residence, this exceptional Rosedale home was thoughtfully reimagined in 2021 under the direction of acclaimed interior designers Michelle R. Smith and Hayley Bridget Cavagnolo. The result is a rare and seamless blend of timeless character and contemporary luxury-refined, welcoming, and rich in detail. Set behind lush landscaping, the home offers striking street presence with a quiet confidence that immediately captures attention. Inside, five bedrooms and five beautifully designed bathrooms are complemented by craftsmanship rarely found. Hand-painted flooring throughout the main level adds subtle artistry, while three wood-burning fireplaces-one anchoring the kitchen-bring warmth and charm to everyday living.The chef's kitchen is both functional and elegant, featuring a Wolf range, Sub-Zero Pro Series refrigeration, an oversized eat-in area, and a walk-out to an expansive deck that seamlessly extends the living space outdoors. A butler's pantry adds thoughtful storage and effortless entertaining appeal.Designed for hosting and relaxing alike, the home features a built-in Sonos sound system throughout the interior and backyard. Outdoors, a private resort-style setting awaits with a saltwater pool equipped with smart heating and lighting-perfect for year-round enjoyment.The third-floor retreat offers exceptional flexibility, complete with a family lounge, workspace, guest bedroom, full bath, and private rooftop deck. On the lower level, a sauna provides a spa-like escape, completing this truly one-of-a-kind Rosedale residence.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 March 15, 2026 at 04:15 PM (UTC)
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