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
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
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 details
Nestled on one of Rosedales most esteemed streets, this Georgian-style residence by Brennan Custom Homes harmoniously integrates with the areas historic streetscape while providing modern conveniences throughout. Enter the main floor and into the gracious foyer with mahogany-stained oak hardwood flooring and a grand staircase. The formal dining room, complete with a gas fireplace, sets the stage for cherished family moments. A gourmet kitchen, boasting Calacatta gold countertops and premium stainless-steel appliances, flows seamlessly into the breakfast area and main floor family room. From here, step out to the low-maintenance urban garden stone patio terraces. The main level also features a refined double living room with a gas fireplace. Ascend to the second floor where 3 bedrooms await, including a primary bedroom suite that exudes comfort. This retreat includes a walk-in closet and a 5-piece ensuite spa-like bathroom featuring heated marble floors. Two additional bedrooms, one with its own ensuite, an additional main 5-piece bathroom, provide ample space for family or guests. The 2nd floor dream home office could be converted to a 4th bedroom. The fully finished lower level, with its tall ceilings, expands the living space considerably. It features a recreation/media room with a gas fireplace and built-in cabinetry, an extra bedroom, and a three-piece bathroom. Direct access to the oversized double car garage adds to the practicality of this property. Throughout the home, attention to detail is evident in features such as crown mouldings, perfect architectural balance, and top drawer finishes. This Chestnut Park gold standard address presents a remarkable opportunity to acquire a distinguished residence, just blocks to Yonge St. Enjoy the walkability to vibrant boutiques, cafes, superb restaurants, three racquets clubs and the subway. Close to Ramsden Park and off-leash dog area. Yorkville's global boutiques, cinemas and restaurants are within easy reach.More details
At long last, this grand Edwardian residence in South Rosedale has been completed with perfection by MCR Interiors, offering an exceptional, confident, and fully custom luxury home within walking distance to both Yonge Street and Yorkville. Interiors encapsulate nearly 4000 square feet above-grade with over nine foot ceiling heights on all levels, and offer completely custom, completely new, and completely luxurious interiors. Curated finishes include heated marble floors with herringbone inlays, a beautiful assembly of formal and informal spaces on the main floor, and practical and coveted features such as a large mud room with direct access to the two-car garage. The kitchen is of course completely customized with dove-tailed wooden cabinetry and outfitted with an oversized, top-of-the-line integrated appliance package. A pretty window seat overlooks Rosedale Road, and an amazing walk-in pantry satisfies the practical needs of such a functional kitchen. The home is enlarged by a three-storey glass addition that marries the historic front facade with a modern and exciting rear exterior. On the second floor the addition houses a study or home office, and on the third floor, a children's lounge area for homework or a separate media space. All bedrooms are equipped with individualized ensuite bathrooms. The primary bedroom is most exceptional with incredible proportions, a huge walk-in closet with LED and glass inlays, and an exquisite five-piece ensuite. A large terrace on the second floor is accessed from the primary suite, with a quiet perch above Pine Hill Road and Rosedale Road and cascading views down to Branksome Hall's soccer pitch. The basement was lowered and underpinned and now holds ceiling heights reaching 9'4". It houses a huge recreation space, nanny suite, separate powder room, and a gorgeous walk-in laundry room. This home's versatility can appease families (literally steps to Branksome Hall), or "downsizers" not ready for condo living. A must see!More details
Welcome to a timeless and handsome detached 3 storey heritage Georgian home in the heart of North Rosedale where classic elegance meets everyday comfort. This prestigious area surrounded by parks and ravines in close proximity to excellent private and public schools and access to downtown is ideal for those choosing a healthy family lifestyle. The beautifully landscaped front garden features stone paths flanked by beech trees, boxwood, and yews. Inside, high ceilings along with crown mouldings and two main floor wood-burning fireplaces create a warm, refined atmosphere. The main level showcases a formal living room and dining room, a family room, library and a bright eat-in kitchen and a main floor bathroom. Stained glass windows add beauty and character to the central staircase. The sunlit primary suite offers a fireplace, spacious dressing area and a luxurious 6-piece ensuite featuring a Bagno Italia soaker tub and a walk-in shower for 2! A second floor study with a fireplace and an additional bedroom with an ensuite bathroom complete this second level. The third level includes two generously sized bedrooms and an oversized bathroom. The lower level has a recreation room, fitness area, wine storage, and laundry. A private driveway with decorative pavers runs alongside the home, leading to a detached two-car garage at the rear. Enjoy the fenced south-facing garden with a spacious deck perfect for outdoor entertaining. Steps to Chorley Park, Rosedale Park, and Summerhill Market. Please click on virtual tour for a drone aerial view.More details
A rare blend of heritage charm and modern sophistication, 150 Douglas Drive is a bespoke residence that perfectly captures the essence of Rosedale living, refined, timeless, and deeply connected to nature. Meticulously redesigned by renowned architect Johnson Chou, this home exudes warmth and intention. Interiors are elevated by sculpted ceilings with ambient lighting, in-floor radiant heating, and fully integrated Control4 smart home technology, including fully automated lighting and irrigation systems. Built-in sound spans most of the home and outdoors, complemented by a home theatre system in the family room.The living room is anchored by a striking quartzite fireplace, while the elegant dining room stuns with a custom wine feature. The Poliform kitchen is a dream for the home chef, complete with a large island, premium appliances, and a sunlit breakfast area overlooking the backyard oasis. The adjacent family room offers a relaxed and inviting space to unwind.Outside, a resort-style backyard awaits with a heated Bonavista pool, waterfall feature, and expansive composite deck. A cabana, pergola with built-in television, fire table, and curated lighting create a private outdoor retreat.Upstairs, the primary suite offers vaulted ceilings, dual walk-in closets, and a spa-inspired ensuite. Two additional bedrooms and a stylish family bath complete the second floor. The third floor features a large bedroom and a flexible second room that can serve as either a den or an additional bedroom, along with a full bathroom.The lower level offers excellent ceiling height, a separate entrance, recreation room, office, bedroom, full bath, and bright laundry with pet shower. Additional features include heated front pad and walkways, and a wide mutual drive with backyard access.Beautifully situated on a prime stretch of Douglas Drive, just steps from Chorley Park, ravine trails, and Summerhill shops.More details
Listed by ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM
Set on one of North Rosedale's most established, tree-lined streets, this home is fully finished, meticulously redesigned, and nearly impossible to replicate within a heritage-protected neighbourhood where complete transformations of this calibre are exceptionally rare. With its 128-foot frontage, the property commands an impressive street presence and an estate-like sense of scale.Natural light floods the main level, where the principal rooms overlook a tranquil, green backdrop. The open-concept kitchen and family area connect seamlessly to a private, ravine-like outdoor retreat, perfect for families who travel often or value low-maintenance living. Chefs kitchen with Sub-Zero refrigeration, a Wolf six-burner gas range and microwave drawer, Miele integrated dishwasher, and quartz waterfall countertops anchored by a double-sided porcelain fireplace.Upstairs, four spacious bedrooms offer privacy and flexibility. The primary suite is tucked away, featuring a generous walk-in closet and a spa-inspired en-suite. A secondary suite with its own balcony provides comfort for guests or extended family, while two additional bedrooms share a well-appointed Jack-and-Jill bath. Designer lighting from Union Lighting and wide-plank engineered hardwood flooring add warmth and refinement throughout.The bright, above-grade lower level extends everyday living with a spacious laundry room featuring Electrolux appliances, direct garage access, and a versatile open layout ideal for a home gym, media lounge, or office. Heated driveway and radiant in-floor heating to the NTI high-efficiency boiler, Siemens safety system, and front and rear irrigation for effortless upkeep.A short walk to Chorley Park, Summerhill Market, and the Evergreen Brick Works, and within close proximity to Toronto's top public and private schools, this is a rare turnkey residence that blends Rosedale charm with uncompromising modern luxury.More details
Data was last updated December 27, 2025 at 07:15 PM (UTC)
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