-
18 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12179224
18 Chestnut Park Road Toronto M4W 1W6 
$15,198,000Residential 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 detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
- Contact by Email
-
6 St Margarets Drive in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12) : MLS®# C11949542
6 St Margarets Drive Toronto M4N 3E5
$15,000,000Residential Freehold- Status:
- Active
- MLS® Num:
- C11949542
- Bedrooms:
- 5
- Bathrooms:
- 8
Situated in exclusive Hoggs Hollow, this stunning "French Chateau" nestles on nearly 1 acre backing on to the river; offering complete serenity. It has a strong pedigree, created by Taylor Hannah Architect and Jeffrey Douglas Interior Design, and brought to life by JTF Homes. A circular drive sweeps across the 155 frontage and the house is set well back from the street. With its expansive, 270 wide backyard, with terraces, pool and riverside gardens, it is an oasis of privacy along the tranquil Don River a perfect Country in the City retreat for both family activities and for hosting large gala events! Inside, sunlight dances through the expansive floor-to-ceiling windows, illuminating the elegant spaces. The magnificent great room, featuring a stunning 22-foot-high Indiana stone fireplace and Eramosa stone walls, opens to the terraces and gardens via multiple French doors. The kitchen is a dream-come-true for the serious chef! With 3 workstations, including a large island with breakfast bar, the layout is efficient yet elegant. It opens to an intimate courtyard with pizza oven, where an open-flame fireplace adds to the ambiance. At the west end of the home, the family room features a vaulted ceiling and a stone fireplace. French doors lead you to a very private, covered terrace featuring a true, wood-burning fireplace and a hot tub the perfect place to unwind. The solid-stone stairs in the home are reminiscent of those found in the chateaux of France and reflect the unconditional commitment to quality in the construction of the home. Upstairs, the romantic primary suite features a Juliette balcony and a cozy fireplace. There are 3 additional bedrooms, each with ensuite. The lower level was designed for relaxation and casual entertaining: a spacious recreation/media room, complete with wet bar; a wine cellar with vented cigar room; a spacious exercise room; a spa with steam shower and powder room; a craft room; a hockey room with synthetic ice; and a nannys suite. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
- Contact by Email
-
505 Russell Hill Road in Toronto: Forest Hill South House for sale (Toronto C03) : MLS®# C11947624
505 Russell Hill Road Toronto M5P 2T1
$14,790,000Residential Freehold- Status:
- Active
- MLS® Num:
- C11947624
- Bedrooms:
- 6
- Bathrooms:
- 7
Welcome to 505 Russell Hill Road, a newly constructed masterpiece situated in Toronto's prestigious Forest Hill South neighbourhood. Completed in 2023, this limestone-clad residence exudes timeless elegance and modern luxury, offering over 6,500 square feet of meticulously crafted living space. Designed with an exceptional floor, the home effortlessly connects its inviting living spaces, from the formal dining room to the bright and airy family room. Every room is bathed in natural light, a rare feature made possible by the property's coveted corner lot location and floor-to-ceiling windows. The heart of the home is the gourmet kitchen, outfitted with top-of-the-line appliances and a secondary fry kitchen, ideal for effortless entertaining and everyday living. The seamless indoor-outdoor design extends to the beautifully Landscaped backyard, offering the perfect retreat for relaxation. Upstairs, the second floor is a private haven featuring four generously sized bedrooms, each with its own ensuite and walk-in closet. The fully finished lower level is tailored for luxury and comfort, complete with a home theatre, wine cellar, gym, private-suite, and recreation room, and additional sub-lower level private spa with an indoor pool and hot tub. Nestled in one of Toronto's most desirable neighborhoods, this home is surrounded by the best the city has to offer. Families will appreciate proximity to Canada's top private schools, including Upper Canada College (UCC) and Bishop Strachan School (BSS), while professionals will value the easy commute to the Financial District. World-class healthcare institutions like Mount Sinai and Sunnybrook are nearby, as are the luxury shopping and dining destinations of Yorkville. With stunning design, abundant natural light, and a prime location, 505 Russell Hill Road offers the pinnacle of luxury living. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
- Contact by Email
-
170 Roxborough Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12040761
170 Roxborough Drive Toronto M4W 1X8
$14,499,000Residential 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 detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
- Contact by Email
-
82 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12178239
82 Chestnut Park Road Toronto M4W 2R3
$14,250,000Residential 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 detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
- Contact by Email
-
87 Highland Crescent in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12) : MLS®# C12038270
87 Highland Crescent Toronto M2L 1G7
$13,995,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12038270
- Bedrooms:
- 4
- Bathrooms:
- 6
Welcome to the Weathering Steel House, an architectural masterpiece by Shim-Sutcliffe, overlooking the Rosedale Golf Club. This award-winning home, celebrated with the 2004 Governor General's Architecture Award, harmonizes with its ravine setting through expansive mahogany windows and natural materials. Inside, the living spaces wrap around a stunning two-tiered lily pond and lap pool, inviting nature indoors. The 7,500 sq ft of living space features a gourmet kitchen by Akb Architects, ideal for entertaining.Upstairs, a skylit landing connects three spacious bedrooms, including a serene primary suite with a study, custom closet, and balcony overlooking the pool. The lower level offers a media room, bedroom suite, second kitchen, and gym, all opening to a private garden courtyard. Designed by Neil Turnbull, the garden attracts local wildlife, blending the home seamlessly with its natural surroundings while offering glimpses of the city skyline beyond. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
- Contact by Email
-
113 Donwoods Drive in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12) : MLS®# C12134349
113 Donwoods Drive Toronto M4N 2G7
$13,588,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12134349
- Bedrooms:
- 5
- Bathrooms:
- 7
Nestled beside the Rosedale Golf Course, this much-admired residence in Hoggs Hollow seamlessly blends timeless craftsmanship with contemporary luxury in one of Torontos most prestigious enclaves. Set on a private, beautifully landscaped lot, it offers rare serenity just minutes from the citys core. The grand, light-filled foyer features a dramatic skylight and sweeping staircase, setting the tone for the elegant interiors. The formal living room, ideal for both casual and refined entertaining, opens to tiered stone patios and a lush, south-facing garden. The chefs kitchen is a culinary haven with custom cabinetry, granite countertops, a large island, and premium appliances, flowing into a warm den and refined dining room perfect for hosting. A magnificent two-storey library, clad in walnut paneling, surrounds a fireplace and bookcases, with a mezzanine and study above offering a tranquil retreat. In the main floors west wing, a charming three-season room with a floor-to-ceiling stone fireplace provides a cozy space to enjoy the gardens in comfort. This wing also includes a private office with built-ins, a 3-piece bath, large mudroom with storage, elevator access to all floors, and a direct entry garage. Upstairs, the luxurious primary suite features a fireplace, balcony, spa-inspired marble ensuite, and a custom dressing room with center island. Three additional bedrooms (two with shared ensuite, one with private bath) and an oversized laundry room complete the level. The lower level includes a large rec room, wet bar lounge, home theatre, games room, wine cellar, fitness studio, and a guest suite with kitchenette. Outside, enjoy a private urban oasis with natural pool, twin rockfalls, hot tub, and expansive patios amid mature trees and perennial gardens. The wide 45-ft west yard offers space for play, gardening, or future expansion. Experience the video tour to fully appreciate this exceptional offering. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
- Contact by Email
-
50 Teddington Park Avenue in Toronto: Lawrence Park North House for sale (Toronto C04) : MLS®# C12197126
50 Teddington Park Avenue Toronto M4N 2C6
$11,995,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12197126
- Bedrooms:
- 5
- Bathrooms:
- 8
Infinity House is a masterclass in contemporary architecture - custom-built with state-of-the-art construction techniques and details to deliver a true high-performance house. This luxury home, with 4+1 bedrooms & 8 bathrooms (7,655 sf in total), offers the discerning buyer meticulously conceived interiors that harmonize natural materials with modern elements for the utmost in refined living. This coveted North Toronto location, with its unique blvd & mature tree canopy, is within walking distance to Yonge Lawrence Village & the greens of Rosedale Golf Club. Handcrafted bronze panels fronting the house signal a sublime presence on the street. The entry gallery captures the eye with a stunning living room fireplace with marble slab surround & stairs floating between soaring glass panels & a limestone wall - a true feat of engineering. Reminiscent of the exterior cladding & projecting toward the sky, this imposing feature wall intentionally serves as a central visual anchor. The optimal interior layout flows effortlessly to the professionally designed exteriors through a one-of-a-kind NanaWall of sleek glass panels, welcoming an abundance of natural light. The open concept makes clever use of a floating slat wall to create a sense of division for the dining and living rooms without compromising the bright, airy feel. The family room & adjoining chef's kitchen with pantry & servery is the hub of the home overlooking the backyard oasis with heated pool, terraces & gardens. A study, two powder rooms & a mudroom complete the main level. An elevator opens onto a light-filled 2nd floor, illuminated by custom architectural glazing & leads to 4 bedrooms, including a luxurious primary suite, 4 bathrooms & a well-appointed laundry room. An expansive lower level includes a media/recreation room, custom bar, wine cellar, exercise room with spa steam bath, nanny suite with 3-pc & a 2nd laundry room. EXTRAS: radiant floors, elevator, snowmelt, 2 car heated garage w/lower storage. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
- Contact by Email
-
208 Roxborough Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12166677
208 Roxborough Drive Toronto M4W 1X8
$10,495,000Residential 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 detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
- Contact by Email
-
314 Palmerston Boulevard in Toronto: Palmerston-Little Italy House for sale (Toronto C01) : MLS®# C12096337
314 Palmerston Boulevard Toronto M6G 2N6
$7,500,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12096337
- Bedrooms:
- 5
- Bathrooms:
- 7
Live the unparalleled dream in the former rectory of a 19th century church, a testament to grand architecture, converted to the ultimate in top-tier urban living by carving out an astounding 7,690 sf of finished space at #314 which art lovers will cherish. A unique opportunity on one of Toronto's most beloved streets, this is a super contemporary masterpiece, a crown jewel seamlessly blending history & the ultimate in modern innovation in a loft-like tour de force, with quintessential craftsmanship, designer styling & extraordinary quality behind its elegant, restored facade. Furnishing your most discerning wishes, the clean lines & open flow encompass splendidly spacious rooms, magically skylit interiors, incredible light from vast windows, soaring 14' to 18' ceilings, a striking staircase, a lavish chefs kitchen designed for entertaining, 4 bedrooms, & a 5th now used as a gym, 7 muted marble baths, & a sumptuous primary BR with FP, dressing area, wicc & ballet-bar towel rack. Discreetly positioned for privacy between the welcoming foyer & the Elevator, the ensuite library/home office sanctuary dazzles, underscoring the unparalleled, timeless & refined oasis that is shared by just four. A private PASSENGER, 5-LEVEL ELEVATOR makes this an iconic home you never have to leave, as it accesses every dramatic floor, from the underground parking, right up to the inspired 1,500' low maintenance, canopied, resort-style rooftop terrace, with its focal point CN Tower view, outdoor kitchen, plenty of seating room, sundeck, fireplace, outdoor shower & 2-piece. The walled stone garden off the LR/Great Room, & enchanting gated courtyard entrance, makes all the ample outdoor space remarkable! A CAR ELEVATOR to the massive underground two-car garage ensures luxury car parking safety & provides outstanding storage. Easy to care for, inside & out, unrivaled finishes set this showstopping glory apart. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
- Contact by Email
-
68 Rowanwood Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12094739
68 Rowanwood Avenue Toronto M4W 1Y9
$7,499,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12094739
- Bedrooms:
- 8
- Bathrooms:
- 4
Exquisitely renovated South Rosedale Residence located on a coveted street, just a short stroll from Yonge St. This distinguished, designer's own home exudes timeless elegance & thoughtful design on every level & was reimagined by Baldwin & Franklin Architects with a substantial addition & renovation. A wide 45 ft lot with private drive, detached 2 car garage & stunning landscaping by Janet Rosenberg plus over 5000 sq ft of living space make this home perfectly turnkey for family living. A beautiful home made for entertaining with large principal rooms & gracious proportions. The sun-filled, south-facing living & dining rooms are anchored by a carved limestone gas fireplace, a bay window & a walk out to the manicured front garden a truly serene setting.The kitchen is appointed with high-end appliances, marble countertops & a large centre island. Enjoy the open-concept breakfast area & family room - an ideal setting for hosting.The 2nd level features a luxurious primary retreat with a walk-in closet, a 5-pc spa like ensuite bath & a private terrace. A secondary family room with a gas fireplace along with a beautifully appointed office with custom built-ins, complete this sophisticated level.The 3rd floor features generously proportioned bedrooms, a 3-pc bathroom & a flexible bonus space usable as a 5th bedroom, homework zone, or office.The fully finished lower level has a spacious rec room, a wine cellar equipped with 4 full-sized wine fridges, a laundry room & 2 additional rooms could be used as bedrooms or as an exercise room. Step outside into your private, beautifully landscaped backyard by Janet Rosenberg an entertainers dream with a flagstone patio with seating area, a manicured yard, accent lighting & mature trees lining the perimeter for privacy.Ideally located walking distance to local shops & restaurants, Branksome & Rosedale Ps, TTC, beautiful Ravine trails & Parks. A true Rosedale classic- rare in scale, rich in character & designed for modern living. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
- Contact by Email
-
121 Roxborough Drive in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12163185
121 Roxborough Drive Toronto M4W 1X5
$7,498,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12163185
- Bedrooms:
- 5
- Bathrooms:
- 4
Welcome to a timeless and handsome detached 3 storey heritage Georgian home in the heart of North Rosedale where classic elegance meets everyday comfort. This prestigious area surrounded by parks and ravines in close proximity to excellent private and public schools and access to downtown is ideal for those choosing a healthy family lifestyle. The beautifully landscaped front garden features stone paths flanked by beech trees, boxwood, and yews. Inside, high ceilings along with crown mouldings and two main floor wood-burning fireplaces create a warm, refined atmosphere. The main level showcases a formal living room and dining room, a family room, library and a bright eat-in kitchen and a main floor bathroom. Stained glass windows add beauty and character to the central staircase. The sunlit primary suite offers a fireplace, spacious dressing area and a luxurious 6-piece ensuite featuring a Bagno Italia soaker tub and a walk-in shower for 2! A second floor study with a fireplace and an additional bedroom with an ensuite bathroom complete this second level. The third level includes two generously sized bedrooms and an oversized bathroom. The lower level has a recreation room, fitness area, wine storage, and laundry. A private driveway with decorative pavers runs alongside the home, leading to a detached two-car garage at the rear. Enjoy the fenced south-facing garden with a spacious deck perfect for outdoor entertaining. Steps to Chorley Park, Rosedale Park, and Summerhill Market. Please click on virtual tour for a drone aerial view. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
- Contact by Email
Data was last updated June 18, 2025 at 12:15 AM (UTC)
Eugene Palermo
Chestnut Park Real Estate Ltd., Brokerage