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Showing 1 to 12 of 337 Properties

Listings last updated Monday July 14 2025

170 ROXBOROUGH DRIVE, Toronto (Rosedale-Moore Park), Ontario

$14,499,000 - For sale

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...

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5+1 Bedrooms9-Total 1-Partial Bathrooms

82 CHESTNUT PARK ROAD, Toronto (Rosedale-Moore Park), Ontario

$14,250,000 - For sale

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...

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4+1 Bedrooms6-Total 1-Partial Bathrooms

135 CRESCENT ROAD, Toronto (Rosedale-Moore Park), Ontario

$9,995,000 - For sale

"Horsman Hall" Is A South Rosedale Landmark, And Truly A Rare Offering. The Architecturally Significant Main House Fronts Onto A Semi-Private Road And Has Been Meticulously Restored & Fully Renovated To Expand The Living Area To 5,515Sf. The Main Floor, Graced W/Herringbone Patterned European White Oak Hardwood Flooring & Tiles In An Elegant Palette, Features An Open Living & Dining Room W/Bar Area & Wine Fridge, And A Private...

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7 Bedrooms6-Total 1-Partial Bathrooms

52 ROSEDALE ROAD, Toronto (Rosedale-Moore Park), Ontario

$9,980,000 - For sale

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...

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5+1 Bedrooms7-Total 1-Partial Bathrooms

4403 - 50 YORKVILLE AVENUE, Toronto (Annex), Ontario

$8,980,000 - For sale

Celebrated as one of Toronto's most prestigious and affluent neighborhoods, the Four Seasons Private Residences in Yorkville offer the ultimate in luxury living. Enter through two private elevators to a grand entrance gallery featuring underlit onyx and limestone flooring and soaring ten-foot coffered ceilings. Perfect for refined entertaining, the expansive living and dining area is adorned with six-inch white oak hardwood floors...

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2 Bedrooms3-Total 1-Partial Bathrooms

10 PINE HILL ROAD, Toronto (Rosedale-Moore Park), Ontario

$8,590,000 - For sale

Updated Rosedale Residence at Courts End. What's Better Than That! 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....

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4+1 Bedrooms5-Total 1-Partial Bathrooms

23 SOUTH DRIVE, Toronto (Rosedale-Moore Park), Ontario

$7,654,000 - For sale

Set on an extraordinary 50 ft x 292 ft ravine lot with spectacular park-like vistas, this architecturally distinct 5-bedroom home in South Rosedale blends classic heritage charm and modern design. It offers exceptional privacy and tranquility in the heart of the city. Behind its stately Rosedale façade lies an extraordinary interior where light, scale, and playful sophistication converge. The main floor features a gracious living...

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5 Bedrooms5-Total 2-Partial Bathrooms

205 - 7 DALE AVENUE, Toronto (Rosedale-Moore Park), Ontario

$7,500,000 - For sale

Welcome to Rosedale's premier boutique building, an incredible feat of architectural design and the ultimate in refined living. This 2 bedroom, 3 bathroom suite with family room offers 2,699 sq ft of impeccable curated interior and the highest craftsmanship finishes. This south-facing suite has floor to ceiling windows with two private terraces overlooking the lush ravine and manicured gardens. The soaring 10-ft smooth ceilings with...

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2 Bedrooms3-Total 1-Partial Bathrooms

68 ROWANWOOD AVENUE, Toronto (Rosedale-Moore Park), Ontario

$7,499,000 - For sale

Exquisitely renovated South Rosedale Residence located on a coveted street, just a short stroll from Yonge St. This distinguished, designer's own home exudes timeless elegance & thoughtful design on every level & was reimagined by Baldwin & Franklin Architects with a substantial addition & renovation. A wide 45 ft lot with private drive, detached 2 car garage & stunning landscaping by Janet Rosenberg plus over 5000 sq ft of living...

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6+2 Bedrooms4-Total 1-Partial Bathrooms

121 ROXBOROUGH DRIVE, Toronto (Rosedale-Moore Park), Ontario

$7,498,000 - For sale

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,...

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4+1 Bedrooms4 Bathrooms

304 - 7 DALE AVENUE, Toronto (Rosedale-Moore Park), Ontario

$7,249,000 - For sale

For those seeking something truly special, your spectacular glass treehouse perched above the Rosedale Valley awaits. From the massive expanses of curtain wall glass windows (floor to ceiling) framing nature's changing seasons against the city skyline, to the exquisite natural materials and craftsmanship throughout, Suite 304 at 7 Dale is the very definition of quiet luxury. Experience this extraordinary sun filled apartment with...

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2+1 Bedrooms3-Total 1-Partial Bathrooms

102 - 7 DALE AVENUE, Toronto (Rosedale-Moore Park), Ontario

$6,900,000 - For sale

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 apartment offers all the livability, private greenspace and design aesthetic of a midcentury 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...

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2 Bedrooms3-Total 1-Partial Bathrooms

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