Luxury Homes in Rosedale

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Luxury Houses and Condos For sale in Rosedale

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  • 30 Whitney Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12166017

    30 Whitney Avenue Rosedale-Moore Park Toronto M4W 2A8
    Main Photo: 30 Whitney Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12166017
    $17,300,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12166017
    Bedrooms:
    7
    Bathrooms:
    9
    Rosedale - Toronto's Most Prestigious And Storied Neighbourhoods. Awe-Inspiring 2017 Renovation Of The Highest Standards, This Three-Storey Estate Of 8,881 Sf Plus Its Amenity Rich Lower Level Is Nestled On Over 108' Of Stunning Frontage. Old-World Architecture With A Contemporary Twist. Step Inside To Discover Generously Proportioned Principal Rooms, Soaring Ceilings, Sweeping Grand Staircase And An Effortless Flow Ideal For Both Intimate Family Living And Large-Scale Entertaining. Heated Stone Floors Run Throughout Offering Year-Round Comfort.The Heart Of The Home Is A Chefs Dream Kitchen With Top Of Line Appliances And Seamless Indoor-Outdoor Connection. All Bedrooms With Private Ensuites, Primary Retreat Boasts 6pc Marble Bath, Opulent Boudoir And Dedicated Laundry Facilities. 3rd Storey Is Enhanced With Two Additional Bedrooms Each With Ensuites, Private Kitchenette And Open Sitting Area. The Lower Level Completes This Masterpiece With An Oversized Wine Cellar, Games Room/Media Room, Private Sleeping Quarters And Full Spa With Exercise Room, Indoor Pool Swim Spa And Steam Shower. Outside, Enjoy Lush Professional Landscaping, Unparalleled Privacy And Serenity In The Heart Of The City. A Stunning Concrete Pool With Built-In Hot Tub, A Fully Equipped Outdoor Kitchen. Multiple Seating Areas Perfect For Entertaining Or Serene Relaxation. Rare 3 Gar Heated Garage With Ev Charger. Enjoy The Best Of Urban Living With Close Proximity To Yorkville, Downtown Core, Public Transit, And Torontos Top-Ranked Elite Public And Private Schools. This Is A Once-In-A-Lifetime Opportunity To Own A Landmark Home In One Of The City's Most Coveted Enclaves. More details
    Listed by RE/MAX REALTRON BARRY COHEN HOMES INC.
  • 18 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12179224

    18 Chestnut Park Road Rosedale-Moore Park Toronto M4W 1W6
    Main Photo: 18 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12179224
    $15,198,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12179224
    Bedrooms:
    6
    Bathrooms:
    7
    Located in the prestigious Rosedale neighbourhood, this architectural masterpiece sits on one of the finest streets where there are no visible power lines and no through traffic, as it is comprised of 3 crescent shaped roads. Enjoy a custom architectural steel floating staircase which brings light through the third-floor skylight to lower level wine cellar with a glass ceiling. The finishes are extraordinary, and the layouts on every level are perfect for a family life as well as entertaining. Every bedroom has an en-suite bathroom. The lower level mirrors the luxury above with a fitted bar, 2 storey wine cellar, a billiard room, an exercise room, and a sunken golf simulator. The structure is also in place for the installation of an elevator. What is truly unmatched is the 3-car circular drive as well as a separate coach house with living space above and a double or triple car garage below. Steps to the Rosedale subway and Yonge St. shops. This home is an opportunity to live in true, unsurpassed turnkey luxury. More details
    Listed by CHESTNUT PARK REAL ESTATE LIMITED
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  • 170 Roxborough Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12040761

    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®# C12040761
    $14,499,000
    Residential Freehold
    Status:
    Active Under Contract
    MLS® Num:
    C12040761
    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 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
    Listed by CHESTNUT PARK REAL ESTATE LIMITED
  • 82 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12178239

    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®# C12178239
    $14,250,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12178239
    Bedrooms:
    5
    Bathrooms:
    6
    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
    Listed by CHESTNUT PARK REAL ESTATE LIMITED
  • 902 33 Jackes Avenue in Toronto: Rosedale-Moore Park Condo Apartment for sale (Toronto C09) : MLS®# C12057709

    902 33 Jackes Avenue Rosedale-Moore Park Toronto M4T 1E2
    Main Photo: 902 33 Jackes Avenue in Toronto: Rosedale-Moore Park Condo Apartment for sale (Toronto C09)  : MLS®# C12057709
    $10,500,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C12057709
    Bedrooms:
    3
    Bathrooms:
    4
    Truly one of the finest luxury condominiums in Toronto, Penthouse 902 at 33 Jackes Avenue is an awe-inspiring world class residence perched at the crest of Summerhill and overlooking the treetops of Rosedale. With interiors curated by Powell & Bonnell, the 4482 square foot suite is paired with 1255 square feet of exterior terraces capturing the most unbelievable, unobstructed views of the city every day. A direct private elevator expands into the grand foyer of this suite that is illuminated from the tiered skylight above. Surrounding a wood burning fireplace in the living room, floor-to-ceiling windows connect the unobstructed city landscape to the contemporary spaces within. Stepping out to the nearly 1000 SF terrace (one of four accompanying this suite), the garden beds have been masterfully curated by Mark Hartley Landscape Architects, offering a subtle and elegant array of local trees and shrubs. The views will quite literally give pause to each of your guests, soaking in the inspiring vistas of the city skyline and the treetops of Rosedale. Back in the suite, a custom Neff kitchen was designed to allow for large-scale preparations, and includes a quiet breakfast room recessed into one of the architectural bays of the building. The kitchen connects to the 22-foot dining room with a bay window that absorbs the view of David Balfour reservoir, and further flows to the family room to watch the evening news with cascading views down to the lake as a back drop. A full bedroom suite is revealed on this level, equipped with an ensuite and its own private terrace. To the second level, via ensuite elevator or the custom designed staircase, a broad landing branches to the primary bedroom suite or the home office (equipped with a Murphy bed). Two terraces flank the primary bedroom which is also serviced by an exquisite ensuite bath, a walk-in closet, and exercise space. The home office can easily be converted to a third bedroom, as required. More details
    Listed by CHESTNUT PARK REAL ESTATE LIMITED
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  • 208 Roxborough Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12166677

    208 Roxborough Drive Rosedale-Moore Park Toronto M4W 1X8
    Main Photo: 208 Roxborough Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12166677
    $10,495,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12166677
    Bedrooms:
    5
    Bathrooms:
    5
    An unbelievable, unique opportunity to achieve your great architectural ambition, to create your own dream home on one of the most prestigious blocks in Canada. This iconic Rosedale residence set on a massive ravine lot (88 x 408 ft), only a handful of properties at this scale exist. With groundbreaking approvals to redefine the property that allow you to add a swimming pool, and create a garden oasis with ravine views in Rosedale's most coveted location. Approvals in place for pool and relocation of garage and driveway to create an expansive backyard. The stately home has over 5,000 sq ft above ground and 2,300+ sq ft on the lower level, all of which feature timeless architectural and design elements, including the stunning hand-crafted staircase, multiple original fireplaces, and intricate woodwork. With an enviable primary suite with attached private office, multiple walk-in closets, and an ensuite. Four more well-proportioned bedrooms are found on the second floor. This home can become the perfect narrative for your fabulous life. More details
    Listed by CHESTNUT PARK REAL ESTATE LIMITED
  • 135 Crescent Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12224644

    135 Crescent Road Rosedale-Moore Park Toronto M4W 1T8
    Main Photo: 135 Crescent Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12224644
    $9,995,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12224644
    Bedrooms:
    7
    Bathrooms:
    6
    "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 Library. The Large Kitchen Features A Centre Island, Separate Floating Eat-In Counter, And Is Open To The Family Room W/Sweeping South & West Views Of The Garden & Coach House From The Floor To Ceiling Windows. The Original Leaded Glass Has Been Preserved & Supplemented W/New Large Format Windows. Dramatic, Sun Drenched, Main Staircase. Roof Top Deck W/Views Of Downtown. The Impressive, Light Filled, Lower Level Has Been Selectively Lowered, Finished With Polished Concrete Floors & Includes A Rec. Rm. W/Surround Sound, Wet Bar, Illuminated Glass Wine Display, Home Gym & Bdrm. W/Ens. The Long Gated Driveway Leads You To A Rare Separate 1,900Sf 2-Storey Coach House W/Elevator & 2 Bdrms, Courtyard, Outdoor Cooking Area, & A Muskoka-Inspired 2 Car Garage With EV Rough-In! Steps To Yorkville, Parks, Ravines & Schools. More details
    Listed by RE/MAX REALTRON BARRY COHEN HOMES INC.
  • 52 Rosedale Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12160493

    52 Rosedale Road Rosedale-Moore Park Toronto M4W 2P6
    Main Photo: 52 Rosedale Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12160493
    $9,980,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12160493
    Bedrooms:
    6
    Bathrooms:
    7
    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
    Listed by SOTHEBY'S INTERNATIONAL REALTY CANADA
  • 97 Glen Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12305140

    97 Glen Road Rosedale-Moore Park Toronto M4W 2V5
    Main Photo: 97 Glen Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12305140
    $8,900,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12305140
    Bedrooms:
    7
    Bathrooms:
    9
    A Rare chance in one of the most celebrated neighbourhoods, South Rosedale. Perfectly set back from the main street for privacy, this spectacular oversized lot offers expansive outdoor space upon it's impressive entrance. This is a once-in-a-generation opportunity. Grand, one-of-a-kind estate home in the heart of Toronto's most distinguished neighbourhood. A true Rosedale landmark with historical significance, this magnificent residence exudes timeless sophistication and sits on a prized street with other elegant homes and estates. With a presence like no other, it offers an unmatched blend of heritage, scale, and distinction. Boasting over 8,000 square feet of planned living space, this exceptional property offers unrivaled architectural elegance. Currently under renovation and being sold *as-is*, the home includes approved permits and meticulously designed architectural plans. The plan is a beautiful, timeless vision blending classic traditional design with refined modern touches. A plan that took years to perfect, it offers the ideal balance of elegance, functionality, and lasting appeal. It's grand dedicated spaces and stately proportions will surely satisfy the most discerning taste. This is a home meant for a growing, multi-generational family designed to be cherished and lived in for generations to come. Live surrounded by the best of Toronto just minutes to top private schools, ravines, Yorkville, and the downtown core while enjoying the peaceful charm and exclusivity of one of the city's most celebrated enclaves. Do not miss this legacy in the making. **photos are renderings** More details
    Listed by HARVEY KALLES REAL ESTATE LTD.
  • 10 Pine Hill Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12330644

    10 Pine Hill Road Rosedale-Moore Park Toronto M4W 1P6
    Main Photo: 10 Pine Hill Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12330644
    $7,995,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12330644
    Bedrooms:
    5
    Bathrooms:
    5
    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
    Listed by RE/MAX REALTRON BARRY COHEN HOMES INC.
  • 106 7 Dale Avenue in Toronto: Rosedale-Moore Park Condo Apartment for sale (Toronto C09) : MLS®# C12392355

    106 7 Dale Avenue Rosedale-Moore Park Toronto M4W 1K2
    OPEN HOUSE: Sep 16, 2025
    11:30 AM - 01:30 PM EDT
    Open House on Tuesday, September 16, 2025 11:30AM - 1:30PM
    Main Photo: 106 7 Dale Avenue in Toronto: Rosedale-Moore Park Condo Apartment for sale (Toronto C09)  : MLS®# C12392355
    $7,995,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C12392355
    Bedrooms:
    2
    Bathrooms:
    3
    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 dramatic and memorable first impression and leads to an open concept great room 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 9-piece Gaggenau appliance package with both gas and induction 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. This suite features a Gallery entrance and generous foyer for entertaining and an abundance of storage. Enjoy the ease and convenience of main floor accessibility with 24 hour concierge services just down the hall and potential for a direct private gated access to Dale Avenue (perfect for morning runs or walking the dogs!) 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
    Listed by CHESTNUT PARK REAL ESTATE LIMITED
  • 52 Roxborough Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12317307

    52 Roxborough Drive Rosedale-Moore Park Toronto M4W 1X1
    Main Photo: 52 Roxborough Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09)  : MLS®# C12317307
    $7,800,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12317307
    Bedrooms:
    4
    Bathrooms:
    5
    Set along one of North Rosedales most established and tree-lined streets, this reimagined home offers a rare combination of architectural integrity and modern refinement. The 128-foot frontage provides a sense of space not often found in the city, while inside, the layout unfolds with ease and intention. Natural light fills the main level, where principal rooms overlook a quiet, green backdrop. The kitchen, designed for everyday living as much as entertaining, opens into a warm, inviting family space with seamless access to the private and ravine-like backyard. Upstairs, four well-proportioned bedrooms offer privacy and flexibility. The primary suite is tucked away, with a generous walk-in closet and a spa inspired ensuite that brings a sense of calm. A secondary suite with its own balcony is perfect for extended family or guests, and two additional bedrooms are thoughtfully connected by a shared bath.The lower level is bright and functional, with an above-grade design that welcomes natural light. It features a spacious laundry room with direct garage access and a flexible open layout, ideal for a home gym, media lounge, office, or guest suite. Whether for extended family, work-from-home needs, or future adaptability, this level offers space that evolves with your lifestyle. A heated driveway and walkway lead to an attached garage, plus two-car parking on the driveway for car enthusiasts or additional guests. A short walk to Chorley Park, the Brick Works, and Summerhill Market, and situated near some of the citys top schools. More details
    Listed by FOREST HILL REAL ESTATE INC. and THE AGENCY
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Data was last updated September 13, 2025 at 04:15 AM (UTC)
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