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$11,995,000
5 Beds ⋅ 7 Baths ⋅ C13092402 MLS
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.

20 Cluny Drive, Toronto
$5,850,000
8 Beds ⋅ 6 Baths ⋅ C13080722 MLS
One of the most charming homes in South Rosedale, this exceptional residence blends timeless elegance with the scale and functionality of modern family living. Offering over 5,000 square feet of living space, along with 6+1 bedrooms and 7 bathrooms, the home is thoughtfully designed with beautifully proportioned principal rooms, refined architectural details, and an effortless flow for both everyday living and grand entertaining. A stunning reception hall sets the tone upon arrival, introducing warm, inviting interiors filled with natural light and classic character. The spacious layout includes generous formal and informal living areas, ideal for family life and hosting, while the primary retreat offers a private sanctuary with exceptional scale and comfort. Gated parking for four cars adds a rare level of convenience in this coveted neighbourhood. Nestled among South Rosedale's iconic tree-lined streets and grand heritage homes, the location is unmatched for those seeking both prestige and convenience. Just moments to top private and public schools, beautiful parks, ravine trails, and the shops and dining of Summerhill and Yorkville, this is a rare opportunity to own a distinguished residence in one of Toronto's most sought-after enclaves.

17 Elm Avenue, Toronto
$2,998,000
5 Beds ⋅ 5 Baths ⋅ C13069976 MLS
*Open House Sunday August 16th @ 2pm-4pm* Fabulous contemporary home! Very spacious, approximately 2,200 square feet on three floors with another 700 square feet in the lower level which offers incredible natural light. Detached with four bedrooms, a fifth bedroom/home office in the lower level. Minimalist aesthetic throughout, very stylish and a stunning opportunity in Rosedale on this pretty tree-lined street. Heated Brazilian Ipe hardwood floors throughout, a dramatic glass/steel staircase, large picture windows drenching the house in sunlight and multiple walkouts. The chefs kitchen features a large centre island with breakfast bar, quartz countertops, views over the garden and as well as a concealed office nook. The generous primary retreat offers a bedroom, a sitting area, desk area and a walk-in closet and a spa-like three piece ensuite washroom. The third floor is bright and airy with a sun deck that can be enjoyed to watch the seasons change. The lower level is a seamless extension of the rest of the house with abundant above grade light. The recreation room features a kitchenette affording this level a lot of versatility as a possible in-law suite. A rare garden studio at the rear of the property provides endless possibilities (gym, art studio/workshop) and completes this special offering. Oversized 1-car garage plus additional parking. Walk to area schools including Whitney Public School and Branksome Hall. The Summerhill Market is also just steps away as is Chorley Park and the extensive ravine system. Walk to Rosedale bus at the end of the street for quick transit to Rosedale Station. Excellent access to the Bayview Extension to downtown core in minutes or to the DVP.

44 Standish Avenue, Toronto
$8,990,000
5 Beds ⋅ 7 Baths ⋅ C13024424 MLS
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.

92 South Drive, Toronto
$4,850,000
5 Beds ⋅ 6 Baths ⋅ C13002612 MLS
Luxury meets location is South Rosedale! Nestled in one of Torontos most prestigious neighbourhoods, this South Rosedale gem is part of a rare, exclusive enclave developed approximately 25 years ago. A true prize, this home blends timeless craftsmanship with refined elegance, custom mouldings vaulted ceilings, and top-tier construction speak to its luxurious pedigree.Enjoy unparalleled convenience: you're just a 5-minute walk to the Summerhill subway, fine dining, boutique shopping, and more. This is a rare opportunity to own a distinguished home in a location where luxury truly meets lifestyle.

45 Mathersfield Drive, Toronto
$4,199,000
5 Beds ⋅ 5 Baths ⋅ C13001090 MLS
40 Summerhill Gardens, an exceptional offering in the prestigious Summerhill & Yonge neighbourhood - where refined design meets the serenity of ravine living. This architecturally striking residence offers approximately 4,000 square feet above grade, thoughtfully designed to deliver both elegance and functionality across every level. The main floor unfolds with seamless sophistication, featuring expansive principal rooms ideal for both everyday living and upscale entertaining. A warm gas fireplace anchors the living space, while the open-concept layout flows effortlessly through the living, dining, and family areas. The chef-inspired kitchen is appointed with premium stainless steel appliances, sleek finishes, and ample workspace, perfectly suited for hosting or quiet family meals. Designed with privacy and versatility in mind, the home's 3+2 bedroom, 5 bathroom layout spans multiple levels, offering well-defined spaces for relaxation, work, and recreation. A standout home office, framed by a picturesque ravine backdrop, creates an inspiring work-from-home environment. The primary suite is a true retreat, complete with a spa-like 6-piece ensuite and generous proportions. Additional features include a fully customized home gym, a stylish and functional mudroom, and beautifully appointed secondary bedrooms. Outdoors, a spacious deck provides a tranquil setting for entertaining or unwinding, surrounded by lush ravine views. With parking for three vehicles, including a private garage, and just steps to transit, upscale shops, and acclaimed dining, this residence offers a rare blend of urban convenience and natural beauty-an extraordinary opportunity in one of Toronto's most sought-after enclaves.

40 Summerhill Gardens, Toronto
$5,950,000
5 Beds ⋅ 5 Baths ⋅ C12977932 MLS
SOUTH ROSEDALE AREA! RARE FIND RAVINE VIEWS! ONE OF KIND CONTEMPORARY DETACHED HOME IN 50.5 X 352.69 FEET PREMIUM LOT, IT OFFERS AMIDST RAVINE WITH MATURE TREE VISTAS. THIS BEAUTIFUL HOUSE HAS A VERY COOL INTERIOR LAYOUT & IS INFUSED WITH AN ABUNDANCE OF NATURAL LIGHTS. SPACIOUS 5 BEDROOMS TOTAL OF 6 WASHROOM, 2 BUILT IN CAR GARAGE, 2 DRIVEWAY PARKING AND ADDITONAL 2 CARPORT PARKING SPOTS. THIS 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) ETC. UPON ENTERING THE HOME, THERE IS AN INVITING SUNKEN LIVING ROOM OVERLOOKING SPACES IN DINING ROOM, THESE ROOMS HAVE THE ADVANTAGE OF ENDLESS VIEW OF LUSH GREEN AND BEAUTIFUL RAVINE! KITCHEN HAS BOTH GAS & ELECTRIC STOVES; CENTRAL ISLAND HAS FRUIT SINK, THERE ARE NUMEROUS WALK-OUT TO MULTIPLE DECKS. THE SELF-CONTAINED MASTER ROOM HAS SITTING ROOM; DRESSING ROOMS, THE LOWER LEVEL ENJOY AN INDOOR POOL WITH RAVINE VIEW, EQUIPT WITH SAUNA, WASHROOMS, GREAT ENTERTAINMENT ROOM.

33 Rosedale Road, Toronto
$6,950,000
6 Beds ⋅ 8 Baths ⋅ C12936978 MLS
A Rare Offering In Prestigious South Rosedale. This Exceptional 75-Foot Lot Showcases A Stately Georgian/Palladian Brick Façade. Long Admired And Rich In Architectural Presence. Beyond Its Timeless Exterior Lies A Strikingly Modern, Fully Reimagined Interior That Seamlessly Blends Classic Elegance With Bold Contemporary Design. With Over 6,100 Square Feet Of Living Space, This Residence Is Defined By Pale Oak Flooring, Sculptural Open-Riser Stairs, And Expansive Principal Rooms Designed For Effortless Entertaining. A Sleek, Chef-Inspired Kitchen Is Complemented By A Generous Walk-In Pantry, While The Sophisticated Living And Dining Areas Feature A Custom Wet Bar-Perfectly Balancing Style And Function. The Primary Suite Is A Private Retreat, Complete With A Lavish Six-Piece Ensuite And Bespoke Walk-In Closet With Custom Cabinetry. Additional Bedrooms Are Thoughtfully Distributed Across The Second, Third, And Lower Levels, Each Appointed With Its Own Three-Piece Ensuite, Offering Comfort And Privacy. The Lower Level Provides A Versatile And Inviting Space Ideal For Recreation Or Relaxed Family Living. Outdoors, The Expansive Grounds Present An Opportunity To Create A Resort-Style Setting With Room For A Future Pool. A Detached Two-Car Garage With EV Charging Completes This Outstanding Property. An Exceptional Residence Designed For Elevated Modern Living In One Of Toronto's Most Sought-After Neighbourhoods.

62 Maple Avenue, Toronto
$2,988,000
6 Beds ⋅ 5 Baths ⋅ C12847618 MLS
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.

74 Dale Avenue, Toronto