Rosedale-Moore Park

Rosedale–Moore Park stands as one of Toronto’s most distinguished residential enclaves—a serene world of ravines, winding roads, and timeless architecture tucked moments from the heart of the city. Composed of several highly coveted pockets including Summerhill, North Rosedale, and South Rosedale, this area offers an unmatched blend of natural beauty, refined living, and a warm, community-driven atmosphere that continues to attract families seeking both elegance and everyday comfort. 

South Rosedale, with its grand heritage estates, manicured gardens, and historic mansions set on treelined crescents, is the epitome of classic Toronto prestige. Here, homes sit on generous lots framed by centuries-old trees and lush ravine edges, creating a secluded, tranquil atmosphere just minutes from downtown. 

North Rosedale has its own charming, village-like feel— friendly, walkable, and filled with stately family homes, graceful mature greenery, and beautifully maintained streetscapes. With access to Rosedale Park, tennis courts, community fields, and seasonal events like the muchloved Mayfair, North Rosedale enjoys a spirited yet sophisticated family culture. 

Moore Park, bordering the Beltline Trail and the Moore Park Ravine, offers an idyllic mix of elegant homes and unparalleled access to nature. Its quiet streets, strong school district, and uninterrupted green spaces make it a haven for active families who love walking, cycling, or exploring scenic trails right from their doorstep. 

Summerhill, with its iconic railway station and boutique village core, adds a layer of effortless convenience. Residents enjoy artisanal food shops, gourmet cafés, wine boutiques, charming restaurants, and direct subway access —all wrapped in a refined, welcoming atmosphere. 

Across the entire Rosedale–Moore Park area, families benefit from some of Toronto’s most respected schools, both public and private, as well as boutique shopping districts, historic landmarks, and quick connections to the city’s leading cultural destinations. The ravine system, parks, and forested trails weave the neighbourhoods together, offering endless opportunities for outdoor recreation and peaceful daily routines. 

With stately homes, breathtaking natural landscapes, strong community traditions, and a lifestyle that balances luxury with warmth, Rosedale–Moore Park remains one of the most desirable residential areas in Canada—an extraordinary place for families to grow, connect, and thrive.

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  • House in Toronto

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    Main Photo: House in Toronto
    Residential Freehold
    Raquel Feldberg
    Alan Feldberg
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  • PH1 7 Dale Avenue in Toronto: Rosedale-Moore Park Condo Apartment for sale (Toronto C09) : MLS®# C13525554

    PH1 7 Dale Avenue Rosedale-Moore Park Toronto M4W 1K2
    Main Photo: PH1 7 Dale Avenue in Toronto: Rosedale-Moore Park Condo Apartment for sale (Toronto C09)  : MLS®# C13525554
    $16,500,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C13525554
    Bedrooms:
    4
    Bathrooms:
    5
    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
    Raquel Feldberg
    Alan Feldberg
  • 82 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C13227720

    82 Chestnut Park Road Rosedale-Moore Park Toronto M4W 2R3
    Main Photo: 82 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13227720
    $12,500,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C13227720
    Bedrooms:
    5
    Bathrooms:
    6
    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
    Listed by CHESTNUT PARK REAL ESTATE LIMITED
    Raquel Feldberg
    Alan Feldberg
  • House in Toronto

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    Raquel Feldberg
    Alan Feldberg
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  • 20 Cluny Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C13092402

    20 Cluny Drive Rosedale-Moore Park Toronto M4W 2P7
    Main Photo: 20 Cluny Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13092402
    $11,995,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C13092402
    Bedrooms:
    5
    Bathrooms:
    7
    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
    Raquel Feldberg
    Alan Feldberg
  • 83 Binscarth Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C13640040

    83 Binscarth Road Rosedale-Moore Park Toronto M4W 1Y3
    Main Photo: 83 Binscarth Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13640040
    $11,995,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C13640040
    Bedrooms:
    7
    Bathrooms:
    5
    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
    Listed by CHESTNUT PARK REAL ESTATE LIMITED
    Raquel Feldberg
    Alan Feldberg
  • 170 Roxborough Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C13461906

    170 Roxborough Drive Rosedale-Moore Park Toronto M4W 1X8
    Main Photo: 170 Roxborough Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13461906
    $11,500,000
    Residential Freehold
    Status:
    Active Under Contract
    MLS® Num:
    C13461906
    Bedrooms:
    6
    Bathrooms:
    9
    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 in-ground 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
    Listed by CHESTNUT PARK REAL ESTATE LIMITED
    Raquel Feldberg
    Alan Feldberg
  • House in Toronto

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    Residential Freehold
    Raquel Feldberg
    Alan Feldberg
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  • PH 1 Chestnut Park in Toronto: Rosedale-Moore Park Condo Apartment for sale (Toronto C09) : MLS®# C13781246

    PH 1 Chestnut Park Rosedale-Moore Park Toronto M4W 1W4
    Main Photo: PH 1 Chestnut Park in Toronto: Rosedale-Moore Park Condo Apartment for sale (Toronto C09)  : MLS®# C13781246
    $9,795,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C13781246
    Bedrooms:
    5
    Bathrooms:
    4
    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
    Listed by FOREST HILL REAL ESTATE INC.
    Raquel Feldberg
    Alan Feldberg
  • 20 Whitney Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C13782178

    20 Whitney Avenue Rosedale-Moore Park Toronto M4W 2A8
    Main Photo: 20 Whitney Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13782178
    $8,995,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C13782178
    Bedrooms:
    7
    Bathrooms:
    5
    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
    Raquel Feldberg
    Alan Feldberg
  • 92 South Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C13813766

    92 South Drive Rosedale-Moore Park Toronto M4W 1R6
    Main Photo: 92 South Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13813766
    $8,990,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C13813766
    Bedrooms:
    5
    Bathrooms:
    7
    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
    Listed by HARVEY KALLES REAL ESTATE LTD.
    Raquel Feldberg
    Alan Feldberg
  • 155 South Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C13816450

    155 South Drive Rosedale-Moore Park Toronto M4W 1S3
    OPEN HOUSE: Sep 26, 2026
    02:00 PM - 04:00 PM EDT
    Open House on Saturday, September 26, 2026 2:00PM - 4:00PM
    Main Photo: 155 South Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C13816450
    $7,895,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C13816450
    Bedrooms:
    5
    Bathrooms:
    7
    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
    Raquel Feldberg
    Alan Feldberg
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Data was last updated September 25, 2026 at 06:15 PM (UTC)
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