A truly once-in-a-generation offering, this extraordinary penthouse represents the pinnacle of luxury living. Masterfully designed by internationally acclaimed Paolo Ferrari, this bespoke home offers approx. 4,000 sq ft of impeccably crafted interiors and over 6,400 sq ft of private outdoor living, crowned by an unparalleled 5,000 sq ft rooftop sanctuary overlooking the Rosedale Ravine designed by Janet Rosenberg. A private elevator opens directly into an exclusive vestibule, revealing soaring 10-foot ceilings, exquisite Italian white oak floors, and interiors of timeless sophistication. The grand living room is anchored by a sculptural limestone fireplace and dramatic floor-to-ceiling Reynaers of Belgium curtain wall glazing, while a richly appointed library with custom millwork provides an elegant space. Designed for exceptional entertaining, the formal dining room accommodates 16+ guests and is complemented by a chef's kitchen appointed in Breccia Capraia marble with bespoke cabinetry, a custom breakfast bar, Gaggenau appliances, and impeccable craftsmanship. Every south-facing principal room extends to an extraordinary 1,400 sq ft limestone terrace. Three refined bedroom suites each offer walk-in closets and luxurious ensuites, including an exceptional primary retreat of remarkable scale. The private rooftop is without equal, complete with a resistance pool, hot tub, custom sauna, outdoor kitchen, secluded vegetable garden, Belgian pergola with motorized screens and retractable roof, fire feature, outdoor television, and a dedicated three-piece bath. Complete with a Crestron intelligent home automation system, four-zone climate control, and high-efficiency mechanical systems, every detail reflects the finest international craftsmanship. Situated within Toronto's premier full-service luxury residence by Siamak Hariri, this is a home of extraordinary scale, complete privacy, and unparalleled distinction. Truly one of Toronto's most significant private residences.More details
Listed by ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM
Extremely rare endless summer escape in a poolside paradise with 7-Star resort-style luxury! Experience the ultimate retreat in the most sought-after and prestigious Rosedale neighborhood, west of Mt. Pleasant. Embraced by mature trees and manicured lawns, this extraordinarily expansive 85-foot-wide tableland property sits atop the exclusive Chestnut Park ravine, overlooking serene parkland below and feels like a private country estate. A true garden oasis, the stunning oversized pool is virtually irreplaceable in this area, creating an idyllic opportunity for captivating family living and exceptional entertaining. 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 garden features sprawling multiple terraces for sitting, dining, and entertaining, complete with an outdoor kitchen. Inside, discover gracefully curated interiors & a truly sumptuous sky-lit primary suite with lush treetop views, a sitting area with fireplace, his & her separate dressing rooms and spa-inspired ensuite. This sleek trophy property blends transitional modernity, alluring charm & unparalleled privacy with modern convenience and spectacular luxury in a truly prized neighborhood. Additional highlights include an ELEVATOR, generator, garage with lift & ensuite bathrooms in all bedrooms for superb flexibility. Set beneath a treed canopy for total privacy, you are just steps from the subway, excellent private & public schools, premier shopping, area parks, tennis, skating & hiking & biking trails extending to the lake with Yorkville & the city center only a 10-minute drive away. For those who value permanence, treasured memories will resonate for all in this enduring and stable investment!More details
Discreetly positioned on one of Rosedale's most prestigious streets, this exceptional ravine residence offers rare architectural scale, privacy, and contemporary refinement. Set on a remarkable 238-foot deep lot backing onto the Rosedale ravine, the property boasts a resort-like setting with an infinity-edge pool, expansive outdoor living areas, and a covered terrace designed for year-round entertaining. Situated minutes from downtown Toronto, Rosedale is a unique combination of charm and sophistication. It offers upscale dining, designer shopping, top-rated public and private schools, beautiful parks and endless trails for walking, running or cycling. Quick access to the subway system, Yonge Street and Mount Pleasant Road allow for easy access to explore all that Toronto has to offer. 20 Cluny has been thoughtfully renovated to reflect a seamless blend of timeless architecture and modern luxury. This home spans over 6,000 square feet above grade, with a fully finished lower level, providing elegant space for both grand entertaining and comfortable family living. Inside, 11-foot ceilings on the main and third floors enhance light and volume, while expansive principal rooms offer sophisticated living and dining spaces. The main level, exceeding 2,200 square feet, features a functional layout with formal living and dining rooms, a private office, and a kitchen and breakfast area that connect effortlessly to the terrace and gardens. Upper levels include five generously sized bedrooms, each with its own ensuite. The primary suite offers a serene retreat with a dressing room and spa-inspired bathroom. The third floor provides rare additional living space, ideal for guests or multi-generational living. The lower level includes a recreation room, home gym, and wet bar. Complete with a spacious double garage and heated driveways, this elegant home presents a rare opportunity in one of Toronto's most prestigious neighbourhoods.More details
Listed by ROYAL LEPAGE REAL ESTATE SERVICES PHINNEY REAL EST
This Is One Of Rosedale's Prettiest Renovated "Cape Cods" On North Rosedale's Best Street Amongst Estate Homes. The Interior Is Flooded With An Abundance Of Natural Light & Tall 10' Ceilings On The Main Floor. It Has Excellent Flow For Family & Entertaining. The Rooms Are All An Excellent Size. The Family Room Is Combined With The Open Gourmet Kitchen with a Bistro Style Eat-in Banquet. The Master Is So Romantic With Double Doors To A Treetop South Deck, Ensuite & Walk-In Closets. There Are Another 5 Bedrooms. This Is One Of The Coolest Houses To Come To The Market. The Views To The North Are Park-Like And To The South A Verdant Treed Oasis. In Addition The Garage Has Been Created Into An Enchanting Pavilion For Fun And Play. Beautifully Newer Pool & Spa and Gardens designed by Mark Hartley. Located On A Cul-De-Sac For Road Hockey And Hoops. A Gem! Its a truly a versatile house, for a large family or for a couple seeking tranquility in a Country like private setting and low traffic. A great opportunity. This home lends itself to casual and refined & sophisticated entertaining both inside and outside.More details
An Extraordinary Offering At One Of Rosedale's Most Prestigious & Iconic Addresses. This Magnificent Penthouse Encompasses Over 5,000 Sq. Ft. Of Uncompromising Luxury Within A Landmark Georgian Residence, Masterfully Converted By J.F. Brennan Into Just Four Exclusive Condominium Residences. A Home Of Remarkable Pedigree, Scale & Architectural Grandeur, Offering A Level Of Privacy Rarely Found In Toronto. Private In-Suite Elevator, Providing Direct Access From The Garage Into The Residence & Creating The Feeling Of A Grand Private Estate With The Effortless Convenience Of Condominium Living. Beyond, A World Of Timeless Elegance Unfolds. Soaring 10 & 11 Ft. Ceilings, A Dramatic Staircase, Elaborate Mouldings & Columns, Gleaming Hardwood Floors, Magnificent Marble Fireplaces & Skylights Pay Homage To A Bygone Era, While Exquisite Renovations & Luxurious Finishes Elevate The Home For Modern Living. Palatial Principal Rooms, Bathed In Natural Light, Provide A Spectacular Setting For Grand Entertaining. Two Private Terraces Capture Breathtaking South-Facing Views Across The Toronto Skyline, While The Gourmet Kitchen Walks Out To A Terrace For Seamless Indoor-Outdoor Living. The Expansive Primary Retreat Is A Sanctuary Unto Itself, With A Sitting Area, Two Walk-In Closets & Sumptuous Ensuite With Steam Shower & Bidet. Underground Parking Completes This Irreplaceable Offering. Hidden Away In The Heart Of Rosedale Yet Steps To Yonge St., Shops, Restaurants & Subway. More Than A Condominium, This Is One Of Toronto's Most Unique Private Residences - A Once-In-A-Generation Opportunity To Call An Iconic Rosedale Landmark Home.More details
Situated in the heart of North Rosedale, Whitney Avenue is a picturesque street of established homes set beneath a leafy canopy. For more than a century, it has held sway as one of Toronto's most established addresses; minutes from the ravine and the shops of Yonge and Summerhill, and within reach of the city's best public and private schools. Number 20 is a centre-hall home in the classical style, taken back to its bones and reimagined by designer Connie Braemer in a contemporary renovation featured in House & Home. The result keeps the formality and proportion of the original architecture while opening the house up to create spaces perfectly-tailored for today's families. A striking foyer in concrete-look slab sets the palette that carries through the home: charcoal and warm rift-cut white oak, ebony-stained millwork, and black-framed glass doors that keep sight lines open while defining each room and setting the tone.The formal living and dining rooms at the front of the house have been reimagined through a modern lens while maintaining a sophisticated edge. Behind them, the wall between kitchen and family room has dissolved, creating an expansive open space for family living and entertaining, a striking kitchen anchored by a La Cornue range, and a rare servery kept within the expanded footprint. Oversized sliding doors open the family room onto the patio with outdoor living, swimming pool, and integrated hot tub. Upstairs, the primary suite has two walk-in closets and a marble-look porcelain ensuite, with a second bedroom and dedicated library on the same floor. The third floor holds three more bedrooms, and the lower level adds a recreation room, a wine cellar, and an additional bedroom. Secluded and private, yet minutes from the amenities those who call Rosedale home enjoy.More details
Listed by ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM
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
Welcome to 7 Dale, an exquisite boutique residence by Siamak Hariri and Studio Munge, exemplifying quiet luxury in every thoughtful detail. This fabulous one-of-a-kind home offers all the livability, private greenspace and design aesthetic of a bungalow, set in a newly completed condominium in the heart of Rosedale. Collect art and appreciate great design? A gallery style entrance with large art walls creates a dramatic and memorable first impression and leads to an open concept great room with gas fireplace, perfect for hosting family gatherings, holiday entertaining or simply relaxing in. Enjoy cooking? You will fall in love with the sleek DaDa chef's kitchen featuring huge central island and 10-piece Gaggenau appliance package with both gas and induction cooking options. Adore nature? Massive floor to ceiling glass panels with walkouts from every room frame the changing seasons of your own private outdoor space. The generous dining/seating terrace is sheltered from rain by a bronze canopy and surrounded by lush layers of beautifully manicured gardens. Direct elevator entry from parking level and a generous in-suite storage room complete the picture. Enjoy the ease and convenience of main floor accessibility with 24/7 concierge services just down the hall. Downstairs, a sumptuous spa and fitness club await, fitted with Pent, Peleton and Tonal equipment. A home suited for year round enjoyment or lock and leave to travel at a moment's notice with complete security and peace of mind assured. Mere minutes to the city's finest shopping and dining venues, yet feels like an exclusive retreat a world away from the urban bustle. This is a rare opportunity to enjoy a lifestyle without compromise, combining the unique features of a home with all of the benefits of a condominium.More details
155 South Drive - This is the stunning South Rosedale Home you've been looking for! Commandingly positioned on one of the neighbourhood's most coveted streets, directly overlooking the gated beauty of Craigleigh Gardens, sits an exceptional 4+1 bedroom residence on a spectacular 59' x 149' south & west-facing lot. Almost 7,900 sq. ft. of beautifully finished living space, an Elevator to all 4 levels & that almost impossible-to-find 3-car underground garage! Direct & integrated access from your garage to the house - never think about brushing snow off your car again! Everything is perfectly proportioned: The scale. The light. The incredible Soaring 10' ceilings. A generous & wide hallway w/ rich millwork, beautiful hardwood floors & 3 fireplaces set the stage for grand entertaining without ever feeling overly formal. Fabulous living & dining rooms, a gorgeous panelled library/home office, inviting family room & chef's kitchen w/ lg breakfast area & French doors that spill out to the garden. Upstairs, the primary suite is exactly what you want - sitting room with fireplace, 2 walk-in closets, dressing room & spa-like ensuite. Two additional bedrooms each have ensuites, while the sun-filled 3rd floor is something special: a 4th bedroom, sitting room & incredible wraparound sky terrace with breathtaking treetop & Toronto skyline views that are breath taking. And the garden! Completely private, south & west-facing and beautifully landscaped with huge stone terraces, mature cedar hedging & remote-controlled awnings. Summer dinners, cocktails, kids, dogs - there is room for all of it. The walk-out lower level has a rec/media room, gym or 5th bedroom/nanny suite, steam room & mudroom. Steps to Branksome Hall, Rosedale Jr. P.S, T.T.C., ravine trails & parks and minutes to Yorkville & downtown. Elegant yet incredibly livable. This is a rare gem that you won't want to miss.More details
Listed by ROYAL LEPAGE REAL ESTATE SERVICES OXLEY REAL ESTAT
Data was last updated September 30, 2026 at 07:15 PM (UTC)
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