82 Chestnut Park Road
Rosedale-Moore Park, Toronto, M4W 2R3
FOR SALE
$12,500,000

➧
➧



















Browsing Limit Reached
Please Register for Unlimited Access
4 + 1
BEDROOMS6
BATHROOMS1
KITCHENS10 + 2
ROOMSC13227720
MLSIDContact Us
Property Description
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!
Call
Nearby Intersections
Property Features
Public Transit, Park, Place Of Worship, School, Rec./Commun.Centre, Central Vacuum, Private
Call
Property Details
Address
82 Chestnut Park Road
Community
City
Postal Code
M4W 2R3
Property Type
Detached, Detached
Lot Size
86' x 143'
Taxes
$52,794 (2025
Basement
Finished
Heat Type
Water
Heat Source
Gas
Water
Municipal
Pool
Inground
Parking Spaces
3
Garage Type
Attached
Call
Listing contracted with Chestnut Park Real Estate Limited
Similar Listings
A Rare Offering in Forest Hill, welcome to 94 Dunvegan Rd an exceptional home and lot on one of the neighbourhood's most prestigious and tightly held blocks. Situated on a remarkable 70 x 174 ft lot, this distinguished residence designed by the acclaimed Joe Brennan offers an extraordinary combination of scale, presence, and future potential. From its impressive proportions to its rare indoor 5-car garage, the home stands as a true statement property. Elegant principal rooms, soaring ceilings, wood-burning fireplaces, and oversized windows overlooking the landscaped grounds create a sense of timeless character and warmth throughout. The expansive layout across four levels offers exceptional family living, including a luxurious primary retreat, and 4 more spacious bedrooms with ensuite bathrooms, and a spectacular third-floor loft with skylights, sauna, and wet bar. Whether you choose to enjoy the residence in its current form, undertake a thoughtful renovation, or create a custom-built legacy estate, the possibilities here are as expansive as the lot itself. Opportunities of this size and caliber on Dunvegan Road are exceedingly rare.
Call
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.
Call
A rare statement of architectural distinction, this Forest Hill estate announces itself with quiet confidence and timeless elegance. Designed by award winning architect Richard Wengle and nominated for Luxury Home of the Year, this stately custom residence offers approximately 7,300 square feet of impeccably finished interior space, recently reimagined to exacting bespoke standards.Every detail reflects craftsmanship at the highest level. A slate tile roof and Indiana limestone exterior create a commanding first impression, while the interiors unfold with soaring ceilings, abundant natural light, rich plaster mouldings, and refined architectural finishes. The chef's kitchen by world renowned designer Clive Christian blends beauty and functionality, anchoring the home's principal living spaces.Designed for both entertaining and everyday comfort, the residence features a steam room, trophy wine cellar with brick floors and tasting area, as well as an English style panelled office with custom built shelving. Wellness and convenience are seamlessly integrated with an exercise room, built in speakers, advanced security, and an exceptionally rare six car underground garage complemented by a heated driveway. Outdoors, a landscaped in ground pool, natural stone gas fireplaces, and automated irrigation create a private setting for year round enjoyment. Moments from Yorkville, top private schools, fine dining, and picturesque parks, this is a legacy property in one of Canada's most prestigious communities.
Call
A Custom Built estate of rare distinction, masterfully crafted with an uncompromising commitment to quality, architectural integrity, and timeless design. A commanding gated presence introduces the residence, clad in distinguished Indiana limestone and crowned with a handcrafted copper dome roof-an iconic silhouette of prestige and permanence.The grounds are nothing short of extraordinary, showcasing meticulously curated gardens and masterful landscape design that create a breathtaking arrival and a private botanical sanctuary.Inside, grandeur and functionality exist in perfect harmony. The dramatic entrance hall captivates beneath a soaring double-height domed ceiling, anchored by a sweeping circular staircase and complemented by a private elevator servicing all levels. Principal rooms unfold with effortless flow, framed by expansive windows that capture tranquil garden vistas from every vantage point. Each secondary bedroom is generously proportioned, complete with its own walk-in closet and private ensuite.Ideally situated in the heart of the prestigious Bridle Path-widely regarded among the world's most exclusive neighbourhoods-moments to Sunnybrook Park, premier schools, renowned hospitals, elite golf clubs, the Granite Club, and convenient highway access.
Call
The Moment You Walk Through The Doors To This Wayne Swadron Visionary Masterpiece And Built With Mazenga Craftsmanship, You Will Immediately Be Captivated By Its Sheer Beauty, Modern Feel, Attention To Every Detail and Jaw Dropping Style Throughout. A True Entertainer's Dream Home Both Inside and Out. Nothing Has Been Overlooked. Huge Principal Rooms, Radiant Heated Floors Throughout, Fantastic Flow, 2 Kitchens, 2 Laundry Rooms, Top Notch HVAC, Stunning Spa Inspired Bathrooms and a Primary Suite That Should Be In Magazines. The Focus Of This Awe Inspiring Home is Simple ... Subtle Class in the Front and Dramatic Flare in the Back. Natural Light and Airiness Fill Up Each Room From The Oversized Windows Throughout. The Ultra Private and Stunning Backyard Will Mesmerize You And Make You Feel Like You Are In Your Own Muskoka Paradise. Get Ready To Be Wowed!
Call
MORE THAN JUST A RESIDENCE...A WORK OF ART. Designed by Bill Mockler and Drawing Room Architect Inc. and constructed by Teddington Homes. A sophisticated contemporary design with breathtaking ravine views. The front facade is adorned with a custom carved stone statue, smooth limestone, majestic white flowering pear trees flank the front walkway to a stainless steel & glass double door entry, marble foyer, and 10 ceilings. Natural light throughout the residence with massive floor-to-ceiling windows, skylights, and a striking two-storey foyer inviting the beauty of the outdoors inside. The Great room is balanced with two fireplaces and ever changing seasonal views of the garden, formal dining room with refined details, fireplace, & opens to private patio. Chefs kitchen with seamless cabinetry, immense marble island, premium appliances, breakfast area, servery, and pantry. Family room with custom millwork, fireplace, walk out to the garden, and an exquisite powder room. Luxurious primary suite, six-piece spa bath, massive dressing room (originally planned as a 4th bedroom), two other bedrooms with ensuites, and full laundry room. Lower level with recreation room, additional bedroom/exercise rm, bathroom, second laundry rm and wine cellar. The fluid design creates spacious rooms that engage the senses at every turn with, generous wall space for the art collector, high-end finishes, negative trim detailing, luxurious marble surfaces, custom millwork, archways that stretch to the ceiling, exquisite wood elements, automated blinds that recess into walls, Control4 system for lights, speakers, and security. Spectacular 75 x 300 extremely private lot with inviting gunite pool, sundeck, sitting area and outdoor dining area - an oasis! Unparalleled opulent living for those seeking elegance, style, and ultimate privacy on one of Toronto's most coveted streets. Steps to the Golf Club, Yonge St., close to many private schools: Crescent, Bayview Glen, Toronto French School.
Call
Completely restored and reimagined, Longwood House is a landmark estate tucked within a coveted, private pocket of The Beaches. Once the summer retreat of a 19th-century lumber baron, this iconic residence now unfolds as a masterful fusion of historic grandeur and art deco sophistication.Set across nearly half an acre over two lots, 8 Crown Park Road sits quietly at the end of a secluded cul-de-sac, surrounded by the lush serenity of Ivan Forrest Gardens and overlooking Glen Manor Drive and the Glen Stewart Ravine-a setting that feels worlds away, yet entirely connected.Inside, over 8,000 sq ft spans three beautifully finished levels, where scale and light are elevated by seven walkouts that blur the line between indoors and out. Every detail reflects uncompromising craftsmanship, with globally sourced materials, imported tile from Spain and South America, alabaster lighting, and two bespoke marble-wrapped gas fireplaces.The grounds are a private, curated oasis. With over $1M in landscaping, the property honours its heritage through restored original and rare clinker brick, solid wood soffits, and a hydronic heated driveway, walkway, entry, and garage floor. Ebel stone retaining walls with granite caps frame the landscape, while a black granite rear terrace creates a striking outdoor living space.Elegant, versatile interiors unfold effortlessly-from the stately foyer and sunlit dining room to a Scavolini-designed home office-alongside a gym, games room, two wet bars, wine cellar, and in-law suite potential. Wall-to-wall windows capture uninterrupted ravine and garden views at every turn.Longwood House is not simply a residence-it is The Crown of the Beach. A private park. A legacy property. A rare and remarkable offering.
Call
Tucked Away On A Quiet Cul De Sac In Hoggs Hollow And Backing Onto The Serene Grounds Of Rosedale Golf Club, 12 Winton Road Is A Striking Modern Residence By Arriz + Co Design, Set On A Rare Pie Shaped Lot That Blends Bold Architectural Expression With Refined, Livable Luxury. From The Moment You Arrive, A Fireplace Set Into The Front Window Creates An Unforgettable Introduction And Offers A Glimpse Into The Home's Design. Inside, A Dramatic Concrete Wall Anchors The Staircase, While Skylights And A Suspended Upper Hallway Draw Natural Light Deep Into The Space, Creating A Sense Of Openness Throughout. The Principal Rooms Are Connected And Defined, With The Living And Dining Areas Separated By A Sculptural Three Sided Fireplace, While The Office Is Set Apart By A Built In Aquarium That Adds Calm Without Breaking Flow. The Kitchen Is A True Statement, Outfitted With Top Of The Line Appliances And Wrapped In Marble Slab Surfaces, Seamlessly Connecting To The Family Room And A Rounded Breakfast Bay Overlooking The Private, Tree Lined Backyard. Upstairs, The Primary Suite Features Two Beautifully Designed Dressing Rooms With Custom Millwork And A Spa Like Ensuite, While Three Additional Bedrooms Offer Generous Scale And Their Own Ensuites. A Standout Indoor Outdoor Solarium With Skylights Includes A Hot Tub, Heaters, And A Fridge, Creating A Year Round Retreat. The Lower Level Is Bright And Designed For Entertaining With A Wine Cellar, Full Kitchen, Bar With Built In Marble Island, Gym, And An Additional Bedroom With Ensuite. Outdoors, Heated Steps And Driveway, Curated Landscaping, And A Secluded Backyard With A Custom Gib San Pool And Fire Table Complete This Private Setting. A Rare Offering Where Architecture And Setting Come Together Seamlessly, This Is Escapism In The City.
Call
Rarely offered contemporary custom crafted home in prime Lawrence Park. Quiet treelined street, sensational curb appeal with limestone, brick exterior, large floor to ceiling windows. Quality finishes throughout, cohesive designing and modern layout. Exceptional Great Room combining casual living space, dining and spectacular eat-in kitchen with clean lines and integrated finishes. Expansive glass windows and doors, all overlooking the incredible backyard pool, cabana and entertainer patio. Perfectly positioned powder room off the mudroom which has side door entry and direct access to the double car garage. Primary suite with a treetop view of the pool, 5 piece ensuite bathroom and unreal dressing room fit with a custom closet system. 3 remaining bedrooms with ensuite bathrooms and walk-in closets. Second floor laundry room for ease and convenience. 10 ft ceilings on the main floor and second floor. Sensational basement (9 foot ceilings) with supersized family room, the generous proportions allow for entertainment area and games room. There is a bonus home gym and an additional bedroom with 3-piece ensuite bathroom. This house boasts incredible natural light, custom paneling, oak hardwood floors and heated porcelain tile floors throughout. The backyard has been designed for entertaining in the city. The covered patio with gas fireplace is perfect for entertaining and the salt water pool and sundeck will keep the kids happy. The rear cabana offers bonus climate controlled space year round. Landscaped with column trees and sleek metal fencing for the ultimate in privacy. No expense spared in the construction of this contemporary masterpiece.
Call
* Landmark Lawrence Park Estate Home On Incredibly Private South Lot Spanning 3/4's Of An Acre * Meticulously Renovated Back To The Studs With The Highest Caliber Transitional Finishes * Impressive Principal Rooms & Great Flow For Entertaining * Modern Chef's Kitchen With Breakfast Area And Walk-in Pantry * Open Concept Family Room Walks Out To Backyard Oasis * Luxurious Primary Suite Featuring Designer 5 Piece Marble Ensuite * Five Generous Upstairs Bedrooms * Exceptional Lower Level Offers Multifunctional Recreation Room, Bar Area, Exercise Room, 3 Piece Bathroom, Large Laundry Room, Sauna, Custom Built-in Closets, Lots Of Storage And Furnace Room * Lush Manicured Grounds With Private Front Garden, Large Side Yard, Covered Back Patio, Inground Pool And Cabana * A Must See! *
Call
Striking contemporary façade in limestone and brick, complemented by a private at-grade driveway, built-in garage and full snow-melt system including all walkways and patio.The interior offers a refined transitional design with 10' ceilings on the main floor. Elegant combined living and dining spaces flow seamlessly into a spectacular rear great room with a beautifully appointed eat-in kitchen and butler's pantry. A dramatic 17' wall of glass opens the family room to the outdoors, creating an effortless indoor-outdoor lifestyle. Two main floor offices provide rare and versatile work-from-home options.The upper level features five generously sized bedrooms, highlighted by a truly exceptional primary suite.The fully finished lower level is designed for both comfort and lifestyle, complete with radiant in-floor heating, a state-of-the-art media room, home gym with sauna, extensive custom storage, and direct access to the garage.The private, landscaped backyard is a true resort-style retreat, featuring a sensational pool and hot tub, outdoor cabana with washroom and change room, and a beautifully crafted stone patio-for exceptional year-round and seasonal enjoyment.
Call
Prestigious Bridle Path Ravine Mansion on Exclusive Enclaves of Glenorchy. Modern French Chateauesque with Renaissance Design. Renowned Hovan-Homes Masterpiece. Soaring 25 Ft Ceiling Anchors Grandeur Foyer and Symmetrical Layout. Upscale Finishes Acclaims Both Contemporary Living & Timeless Elegance. Total Appx 7,366 Sf Luxurious Interior. Above 5,564 sf. Walkout Lower Level 1,802 Plus 3-Car Garage. Upper Four Ensuite Bedrooms, Downstair Guestroom & Nanny's Quarter. Lavish Walk-in & Walk-through Wardrobes. Culinary Maple Kitchen. Hand-painted Royal Library. Salon Style Gallery Hallways. Segmental Arches, Detailed Dormers, Curved Staircase, Cast Iron Accents, and Silk Fabric Walls Consistently Honouring the Homeowner's Fine Taste. Sitting atop of Acres of Lush Glendon Forest & Sunnybrook Park to Enjoy Panoramic Greenery & Private Oasis. Perfect Proximity to Granite Club, Golf Courses, Crescent, Harvergal, T.F.S., U.C.C., Crestwood & Wealth Choice of Top Ranking Public & Private Schools.**EXTRAS** Enhanced Outdoor Living Adored Professionally Crafted Front & Back Gardens, Grotto Patio & Natural Stone Paths, Circular Driveway Extending Long Inner Drive, and unparalleled ravine
Call
For The Discerning Buyer W/ An Architectural Eye & An Appreciation For The Finest Luxury Finishes, This Award-Winning Smart Home Is A True Design Masterpiece. Situated On A Prestigious Crescent, This Custom Estate Offers Over 10,341 Sq. Ft. Of Exceptional Living Space & Showcases An Extraordinary Blend Of Elegance, Craftsmanship, & Modern Luxury. Designed & Built By The Renowned Venetian Group Homes For The Builder's Own Family, No Detail Was Overlooked. The Striking Exterior Features Rare Indiana-Cut Limestone, Verona Gold Marble Accents, Belden Brick Detailing, & A Heated Circular Driveway. Inside, Soaring 11-Foot Ceilings, Exquisite French Paneling, Heated Floors Throughout The Main Level, Italian Porcelain Slab Flooring, European Chevron Oak Floors, Custom Lighting, & Designer Finishes Create An Atmosphere Of Refined Sophistication. Gr& Formal Living & Dining Rms Are Complemented By A Stunning Library W/A Steam Fireplace. The Family Rm, Galleria, & Breakfast Area Feature Dramatic Coffered Ceilings & Expansive Windows That Flood The Home W/Natural Light. The Designer Kitchen Is Appointed W/ Custom Cabinetry, Premium Appliances, Extensive Millwork, & Impeccable Attention To Detail. A Seamless Walkout Leads To A Glass-Enclosed Outdoor Living Area Overlooking The Resort-Inspired Backyard. The Luxurious Primary Retreat Features Vaulted Ceilings, Custom B/I, A Linear Fireplace, Sitting Area, Bespoke Dressing Rm, & A Lavish Spa-Inspired 16-Piece Ensuite. Designed For Entertaining, The Lower Level Offers A Climate-Controlled 675-Bottle Wine Cellar, Custom Onyx-Faced Bar, Cinema-Quality Home Theatre, Multiple Recreation Spaces, & A Private Nanny Suite. The Professionally Landscaped Backyard Is A Private Oasis Featuring A Betz Concrete Pool W/Waterfall, Jacuzzi, Gazebo, 4-Piece Pool Bath, & An Extra-Wide Walk-Up To The Rear Yard. A Rare Opportunity To Own One Of The Area's Most Distinguished Custom Estates, Where Architectural Excellence Meets Uncompromising Luxury.
Call
***Magnificent***chateau-inspired***an exclusive-gated entrance & circular driveway lead to the L-U-X-U-R-Y grand residence on a beautiful 100ftx206ft in the prestigious St. Andrew Estate---This estate residence offers over 10,000sf total living space of refined elegance(Apx 7000sf for 1st/2nd floors as per Mpac) & masterfully crafted, palatial interior finishing with sense of European opulence & the utmost in craftmanship & the art of natural sunlight**The main floor welcomes you with a double-soaring ceiling height draws your eye upward with featuring unique-cathedral/dome design with intricate moulding & a curved stairwell with an antique floral railings in timeless elegance. The chef's kitchen balances form of space & function, with a large centre island and breakfast area. The large terrace extends these living spaces outdoors. The family room forms the centre of this home, where family friends/family gathers--------The primary suite elevates daily life, featuring a living room or private library area, double sided fireplace & private terrace with stunning view of green & backyard for quiet moments alone---The expansive ensuite has exquisite materials feels like an European hotel------Thoughtfully designed 2nd primary bedroom offers spacious private spaces for family's senior member-------The rest of bedrooms have own privacy and endless natural lights----The lower level maintains spacious open area with a kitchen-wet bar-large rec room and movie theatre & lots of storage area & easy access to a private backyard***3 Furnaces/3 Cacs--Private ELEVATOR--CIRCULAR DRIVEWAY WITH 3 CARS GARAGE--GATED HOME & MORE!!
Call
Exceptional 75 x 175 ft premium lot,This distinguished pink stone residence, originally built in 1913, is a rare offering in the prestigious neighbourhood of Forest Hill. Rich in history, the property once operated as the renowned Cantab College boys' school during the Depression years before being acquired by the current owners in 1985. The home was meticulously restored and thoughtfully updated, including a seamless stone-clad main floor addition that blends beautifully with the original architecture.The elegant main floor features a welcoming vestibule and grand hall, a cozy library, an entertainment-sized dining room with fireplace, and a gracious living room with bay window and fireplace. Toward the rear, a spacious open-concept kitchen, family, and recreation area with a two-way fireplace overlooks the expansive patio, garden, and swimming pool, creating an ideal setting for both everyday living and entertaining.Upstairs, the second floor offers three bedrooms, including two with ensuite baths, while the third floor provides a substantial bedroom or sitting suite with a three-piece ensuite and cedar closet. The lower level, with 7-foot ceilings, includes a gym and home theatre area with fireplace, additional living quarters, and extensive storage including a wine cellar. The home occupies only a portion of the site, presenting rare potential for future redevelopment or expansion in one of Toronto's most coveted residential enclaves. The property also includes a detached two-car garage with a pool cabana and washroom.Located minutes from two of Canada's most prestigious private schools, Upper Canada College and Bishop Strachan School, this unique residence offers a remarkable opportunity to enjoy its historic charm today while holding significant long-term potential.
Call
Welcome to an exceptional residence of unparalleled craftsmanship in the heart of prestigiousLytton Park. Masterfully designed by architect Lorne Rose, 239 Cortleigh Boulevard is a 5 bed, 7 bath home with a seamless blend of artistry and the finest of materials across all 8,285 sqft of living space. Upon arrival, a heated limestone walkway leads to an opulent entrance framed by a limestone facade, where a grand foyer captivates with heated white marble flooring in laid with metal accents. Custom stone, velvet paneling, mirrored surfaces, and brass fixtures set a tone of luxury. The formal dining room features a striking marble fireplace and a built-in marble wine wall. The kitchen is a culinary showpiece with a large marble island, matching countertops and backsplash, a Lacanche gas range, Sub-Zero paneled fridge and freezer, Miele appliances and a butlers pantry. The adjoining family room has a custom marble feature wall with gas fireplace and 12-foot sliding glass doors opening to a heated covered terrace with an outdoor kitchen. The backyard is a private oasis featuring a limestone patio, irrigated landscaping, and a custom concrete pool with waterfall and hot tub. The opulent second floor primary retreat features bespoke millwork, marble gas fireplace and a wet bar. The spa- inspired suite features a white marble heated floor and a walk-in spa shower. Dual walk-in closets, complete with a backlit onyx stone island, custom cabinetry, and an Onyx makeup station are dazzling. The four additional bedrooms are impeccably appointed featuring ensuite baths, heated floors, and designer finishes. The lower level is an entertainers paradise, boasting a home theatre, a sleek marble bar, and a full-size gym. A cabana-style change room allows for direct pool access, plus a nanny suite and secondary laundry. Every detail in this stunning residence has been meticulously curated to deliver an unparalleled living experience just moments to extraordinary amenities.
Call
Call















