Find Homes for Sale in Rosedale, Toronto, Canada
Welcome to the premier resource for finding homes in Rosedale, one of Toronto’s most prestigious neighborhoods. Our exclusive listings feature a variety of luxurious properties, perfect for those seeking an upscale and elegant living experience. Discover the charm and sophistication of Rosedale and find your ideal home with our curated selection, detailed information, and expert guidance.
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46 Mathersfield Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12733464
46 Mathersfield Drive Toronto M4W 3W5 
$3,675,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12733464
- Bedrooms:
- 4
- Bathrooms:
- 5
Welcome to 46 Mathersfield Avenue, an elegant semi-detached home tucked away on a quiet cul-de-sac in the heart of South Rosedale, one of Torontos most prestigious and picturesque neighbourhoods. This rare "25 year new-build" blends timeless sophistication with modern comfort, offering approximately 3,500 sq. ft. of living space across all levels. Set within one of the most coveted areas in the city this home combines classic character w/ soaring 11' ceilings in the kitchen/family rm & w/ contemporary conveniences incl. a 2-car garage, updated systems, & designer finishes thru/out. The stunning entrance features a custom front door by Amberwood leading to a combined living/dining rm w/ crown moulding & a cozy gas fireplace. Step down to the heart of the home where a spectacular kitchen / family room by RN Design & KGA Kitchens, features custom cabinetry, quartz counters, Sub-Zero & Wolf appliances, an oversized island w/ breakfast bar & walk-in pantry. The rear of the home is flanked w/ floor-to-ceiling windows & opens to a private landscaped garden perfect for entertaining or quiet evenings. Upstairs, the primary suite is a serene retreat w/ a Juliette balcony, walk-in closet, & renovated 5-piece ensuite w/ freestanding tub, double vanity & glass rain shower. Two additional bedrooms are both generous in size & each feature ensuite baths - a rare find in this area. A massive skylight above the architectural curved staircase fills the home w/ light & the finished lower level has a lg rec rm w/ gas f/pl, a huge gym, 4th bedrm & 3-piece bath.. The L.L. has above-grade windows ideal for family living or guests. Professionally landscaped front and rear gardens by David Scott Designs featuring new stonework, fencing, a Sundance hot tub, & gas lines for outdoor BBQ. Steps to Rosedale Jr P.S, Branksome, U.C.C. York, Greenwood & TTC. Enjoy the perfect blend of ravines, parks & urban shops & restaurants just minutes from your door - privacy & luxury in the heart of the city. More detailsListed by ROYAL LEPAGE REAL ESTATE SERVICES OXLEY REAL ESTATE- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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92 South Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12731854
92 South Drive Toronto M4W 1R6
$8,990,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12731854
- 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 detailsListed by HARVEY KALLES REAL ESTATE LTD.- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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80 Douglas Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12720268
80 Douglas Drive Toronto M4W 2B4
$5,890,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12720268
- Bedrooms:
- 5
- Bathrooms:
- 5
Nestled in the heart of Toronto's prestigious North Rosedale neighborhood, this property is a quintessential "rare gem" offering timeless elegance on an expansive 46.67 x 140-foot lot. This stately built, three-story detached residence presents a rare resale opportunity for those seeking a blend of historic charm and modern family functionality.Designed for both sophisticated entertaining and comfortable daily living, the home features grand-scale principal rooms, five spacious bedrooms, and five updated bathrooms across nearly 5,000 square feet of finished space. The property is ideally situated within walking distance of the city's top-tier private and public institutions, including Whitney Junior Public School, making it a premier choice for families. More detailsListed by T-ONE GROUP REALTY INC.,- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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52 Rowanwood Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12713218
52 Rowanwood Avenue Toronto M4W 1Y7
$4,495,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12713218
- Bedrooms:
- 5
- Bathrooms:
- 5
Nestled on one of Toronto's most iconic tree-lined streets, just steps away from the vibrant Yonge Street, you'll discover the exquisite 52 Rowanwood Avenue. This beautifully updated 5-bedroom family home has been cherished and meticulously maintained by the same family for 25 years, showcasing a perfect blend of character and modern amenities. The main floor is an entertainer's dream, featuring a stunningly renovated kitchen that seamlessly flows into a landscaped backyard oasis, perfect for outdoor gatherings. The brand-new butler's pantry conveniently services the oversized dining room, making hosting dinner parties a delight. After a meal, retreat to the inviting living room, where a cozy wood-burning fireplace provides warmth and ambiance. With abundant natural light and ample seating, this space is ideal for relaxing or gathering around the grand piano to create unforgettable memories. Ascend to the second floor, where you'll find a generously proportioned primary suite complete with a private two-piece bath. This level also boasts a brand-new five-piece bathroom, a guest room, and an oversized study and family room, offering versatility for work or leisure. The third floor features two additional spacious bedrooms, including one with a newly renovated ensuite, along with a convenient laundry room that provides ample storage. This home truly offers a harmonious blend of comfort, style, and functionality, making it a perfect haven for family living. The lower level features a spacious recreation area, a home gym, ample storage, and a three-piece bathroom. Step outside to the private, fully fenced west-facing backyard, where a sun-soaked deck is enhanced by seasonal tree canopies and integrated stonework, creating a serene outdoor retreat More detailsListed by BOSLEY REAL ESTATE LTD.- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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91 Glen Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12715240
91 Glen Road Toronto M4W 2V5
$2,749,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12715240
- Bedrooms:
- 3
- Bathrooms:
- 4
Exuding timeless elegance, this South Rosedale townhome was designed by renowned custom homebuilder Joe Brennan. Nestled on a winding, tree-lined section of Glen Road with a long setback from the road to ensure privacy. With over 3,300 sq ft across three levels, this home offers a seamless layout with the opportunity to customize as needed. The main floor of this home is truly a 'wow' - oversize in scale with high ceilings and well-suited for entertaining. Featuring magnificent natural light cascading from multiple skylights, rich dark hardwood flooring and a wood-burning fireplace flanked by large picture windows overlooking the garden. The formal dining room features beautiful panelling, built-in shelving, and a convenient servery leading to the thoughtfully-designed kitchen. On the second floor, the massive primary bedroom offers a bright and airy ensuite with skylight, and the spacious second bedroom has its own ensuite and a walk-in closet. Ample space on the second floor offers the possibility to reconfigure for three bedrooms. The above-grade ground level offers a family room / office with a gas fireplace, large picture windows, and a walk-out to the garden. Truly an enviable location, access to Craigleigh Gardens park and Milkmans Lane trail is just around the corner for a peaceful retreat under the tree canopy. Toronto's finest private and public schools including Branksome Hall and Rosedale Jr Public School are nearby. Situated just steps to the bus stop and walking distance to both Rosedale and Castle Frank subway stations ensures that you are well connected to the city. Rare three-car parking with an integrated garage providing direct access to the home and a long private interlocking brick drive. This is a wonderful opportunity for discerning buyers seeking the lifestyle and tranquility of this coveted neighbourhood. More detailsListed by SOTHEBY'S INTERNATIONAL REALTY CANADA and Sotheby's International Realty Canada, Brokerage- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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52 Rosedale Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12709212
52 Rosedale Road Toronto M4W 2P6
$8,980,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12709212
- 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. 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. 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. More than meets the eye, deceptively large rear garden offers an abundance of space for outdoor enjoyment including a plunge pool, if so desired. 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 detailsListed by HAZELTON REAL ESTATE INC.- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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104 Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12697034
104 Park Road Toronto M4W 2N7
$8,950,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12697034
- Bedrooms:
- 5
- Bathrooms:
- 5
Originally a stately classic residence, this exceptional Rosedale home was thoughtfully reimagined in 2021 under the direction of acclaimed interior designers Michelle R. Smith and Hayley Bridget Cavagnolo. The result is a rare and seamless blend of timeless character and contemporary luxury-refined, welcoming, and rich in detail. Set behind lush landscaping, the home offers striking street presence with a quiet confidence that immediately captures attention. Inside, five bedrooms and five beautifully designed bathrooms are complemented by craftsmanship rarely found. Hand-painted flooring throughout the main level adds subtle artistry, while three wood-burning fireplaces-one anchoring the kitchen-bring warmth and charm to everyday living.The chef's kitchen is both functional and elegant, featuring a Wolf range, Sub-Zero Pro Series refrigeration, an oversized eat-in area, and a walk-out to an expansive deck that seamlessly extends the living space outdoors. A butler's pantry adds thoughtful storage and effortless entertaining appeal.Designed for hosting and relaxing alike, the home features a built-in Sonos sound system throughout the interior and backyard. Outdoors, a private resort-style setting awaits with a saltwater pool equipped with smart heating and lighting-perfect for year-round enjoyment.The third-floor retreat offers exceptional flexibility, complete with a family lounge, workspace, guest bedroom, full bath, and private rooftop deck. On the lower level, a sauna provides a spa-like escape, completing this truly one-of-a-kind Rosedale residence. More detailsListed by SAGE REAL ESTATE LIMITED- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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6 Jean Street in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12687738
6 Jean Street Toronto M4W 3A7
$2,479,999Residential Freehold- Status:
- Active
- MLS® Num:
- C12687738
- Bedrooms:
- 4
- Bathrooms:
- 2
Welcome to 6 Jean Street, a beautifully renovated family home offering 4 bedrooms and 2 bathrooms in one of Toronto's most desirable neighbourhoods. Fully gutted to the bricks in 2013/14, this residence was thoughtfully rebuilt with new electrical, mechanicals, flooring, furnace, appliances, and a complete interior redesign blending character with modern convenience. The home is walking distance from two of the highest-rated public and Catholic schools in the province (Whitney Junior Public School and Our Lady of Perpetual Help). Excellent private school options such as Branksome Hall are also nearby, making this location ideal for families seeking premier education. Outdoor enthusiasts will love the short stroll to Rosedale Park, Chorley Park, and Evergreen Brickworks. A TTC bus stop at the end of the street connects directly to Rosedale Station, offering quick access downtown. Inside features include heated bathroom floors, a Stûv wood-burning fireplace by Classic Fireplace, and custom blinds (2018) on the bay window and bedrooms. Speaker wire and Ethernet run throughout the home for seamless connectivity. The basement was finished in 2023 including a sump pump and heater, while the upstairs laundry received new updates this past spring. A ductless AC unit serves the third floor, ensuring comfort year-round. Exterior upgrades include full waterproofing, landscaping (2014), front deck (Trex), rear deck, and shed. The roof was redone in 2024 with new sheeting, shingles, and a flat section at the rear. Parking is stress-free with city permits, and the dead end street itself is welcoming, safe, and family-friendly, with easy parking for guests. Just minutes from Summerhill Market, local shops, a pharmacy and café, this cherished home offers the perfect blend of community charm and urban convenience. More detailsListed by UNION REALTY BROKERAGE INC.- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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74 Dale Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12676562
74 Dale Avenue Toronto M4W 1K9
$2,988,800Residential Freehold- Status:
- Active
- MLS® Num:
- C12676562
- Bedrooms:
- 6
- Bathrooms:
- 5
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. More detailsListed by MINMAXX REALTY INC.- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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20 McKenzie Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12670634
20 McKenzie Avenue Toronto M4W 1J9
$3,995,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12670634
- Bedrooms:
- 4
- Bathrooms:
- 4
Welcome to 20 McKenzie Avenue, a timeless gem in prestigious South Rosedale. Built in 1908, this stately home blends historic charm with modern comfort, offering a warm and sophisticated lifestyle in one of Toronto's most coveted neighbourhoods. Set back gracefully from the street, the property is framed by mature trees, landscaped gardens with beautiful southern exposure, and a private cobblestone drive with garage, featuring classic design with sophisticated curb appeal. Inside, the main floor flows beautifully through bright, well-proportioned rooms. The formal living room features hardwood floors, a wood-burning fireplace, and large windows overlooking the garden and flagstone patio. The updated, eat-in kitchen offers abundant cabinetry and counter space, opening to a formal dining room with French doors that open onto the wonderful private garden - perfect for entertaining or relaxed family dinners. A cozy, wood-panelled family room/library with built-in bookcases and a gas fireplace provides a comfortable retreat for reading or quiet evenings. Upstairs are three spacious bedrooms, including a primary suite with vaulted ceilings, walk-in closet as well as a wall to wall closet and a luxurious 5-piece ensuite. Skylights fill the second floor with natural light, creating a bright, airy atmosphere. The finished lower level includes a large recreation room with a gas fireplace and built-ins, a guest or nanny suite, 4-piece bathroom, a wine cellar, an extra-large laundry room, a tool/work room, and ample storage throughout. Ideally located, this exceptional home is steps from the TTC, walking distance to Branksome Hall and other top schools, and offers easy highway access with a quick drive to downtown Toronto. 20 McKenzie Avenue combines historic elegance and modern comfort in a coveted Rosedale address. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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7 Beaumont Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12665410
7 Beaumont Road Toronto M4W 1V4
$9,980,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12665410
- Bedrooms:
- 6
- Bathrooms:
- 5
Rare opportunity to restore a distinguished historic Rosedale residence to its original architectural integrity & create a bespoke home of exceptional grace & distinction, ideally positioned on one of Rosedale's most admired & private streets. Set on a wooded ravine-adjacent property surrounded by mature trees & prestigious estate homes, this residence offers a tranquil & picturesque setting that seamlessly blends privacy, prestige, & enduring connection to nature. The natural ravine backdrop provides year-round beauty & sense of retreat rarely found so close to the city's core. Classic proportions & refined period details define the home, including original hardwood floors, soaring ceilings, hand-carved mantlepieces, elaborate plaster crown mouldings, & a richly paneled library that reflects timeless craftsmanship. Grand principal rooms & elegant floor plan create exceptional flow & present rare canvas for thoughtful restoration & modern luxury. Location is equally compelling. Chorley Park & Craigleigh Gardens offer scenic hiking, jogging, & cycling trails that lead directly to the Evergreen Brick Works & connect to the extensive Don Valley park system. Nearby Rosedale Park & Ramsden Park provide tennis courts, skating rinks, & wading pools, while Mooredale House is a popular community centre. Summerhill Market, & fine shopping, dining, & upscale boutiques are found along the vibrant Yonge Street corridor. Public transit is readily available Motorists enjoy quick access to the Don Valley & downtown financial district. Some of Toronto's finest public & private schools are within walking distance or easily accessible by transit. Celebrated as one of the city's most prestigious neighbourhoods, Rosedale is renowned for its preserved architectural heritage, natural beauty, & exceptional quality of life. 7 Beaumont Road awaits the discerning buyer with vision-one who values history, artistry, and the enduring beauty of classical architecture. Photos virtually staged. More detailsListed by HARVEY KALLES REAL ESTATE LTD.- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
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52 Roxborough Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12660482
52 Roxborough Drive Toronto M4W 1X1
$6,350,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12660482
- Bedrooms:
- 4
- Bathrooms:
- 5
Set on one of North Rosedale's most established, tree-lined streets, this home is fully finished, meticulously redesigned, and nearly impossible to replicate within a heritage-protected neighbourhood where complete transformations of this calibre are exceptionally rare. With its 128-foot frontage, the property commands an impressive street presence and an estate-like sense of scale.Natural light floods the main level, where the principal rooms overlook a tranquil, green backdrop. The open-concept kitchen and family area connect seamlessly to a private, ravine-like outdoor retreat, perfect for families who travel often or value low-maintenance living. Chefs kitchen with Sub-Zero refrigeration, a Wolf six-burner gas range and microwave drawer, Miele integrated dishwasher, and quartz waterfall countertops anchored by a double-sided porcelain fireplace.Upstairs, four spacious bedrooms offer privacy and flexibility. The primary suite is tucked away, featuring a generous walk-in closet and a spa-inspired en-suite. A secondary suite with its own balcony provides comfort for guests or extended family, while two additional bedrooms share a well-appointed Jack-and-Jill bath. Designer lighting from Union Lighting and wide-plank engineered hardwood flooring add warmth and refinement throughout.The bright, above-grade lower level extends everyday living with a spacious laundry room featuring Electrolux appliances, direct garage access, and a versatile open layout ideal for a home gym, media lounge, or office. Heated driveway and radiant in-floor heating to the NTI high-efficiency boiler, Siemens safety system, and front and rear irrigation for effortless upkeep.A short walk to Chorley Park, Summerhill Market, and the Evergreen Brick Works, and within close proximity to Toronto's top public and private schools, this is a rare turnkey residence that blends Rosedale charm with uncompromising modern luxury. More detailsListed by FOREST HILL REAL ESTATE INC.- DARYL KING
- RE/MAX HALLMARK REALTY LIMITED
- 1 (905) 9075464
- homes@darylking.com
Data was last updated January 28, 2026 at 03:15 AM (UTC)
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