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18 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C11942679
18 Chestnut Park Road Toronto M4W 1W6 
$17,270,000Residential Freehold- Status:
- Active
- MLS® Num:
- C11942679
- Bedrooms:
- 6
- Bathrooms:
- 7
Nestled in the heart of the prestigious Rosedale neighborhood on one of its most coveted streets, this extraordinary 7,000+ sq ft home stands as a true architectural masterpiece. In addition to the breathtaking 3-storey main residence, the property features a two-storey garage/coach house and a striking circular driveway, surrounded by lush landscaping and ample parking for up to 7 vehicles. A stunning custom backlit steel staircase spirals upward through the centre hall and is crowned by an oversized skylight that floods the space with natural light. The home boasts 5 spacious bedrooms, each with its own ensuite and generous closet space. An expansive central hall leads to an elegant double living room with a fireplace, complemented by a formal dining room perfect for hosting. The gourmet kitchen and adjoining family room are ideal for both daily living and entertaining, with a large wood-burning fireplace and a wall of glass doors that open up to the serene garden beyond. The lower level takes luxury living to the next level, featuring a sunken golf simulator, a family room, a games room, a fully-equipped gym, and an impressive built-in stone bar. This home offers unparalleled style, comfort, and sophistication at every turn. **EXTRAS** 7 car parking with fully finished coach house/garage circular drive. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
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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
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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
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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
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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
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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
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- 416-925-9191
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902 33 Jackes Avenue in Toronto: Rosedale-Moore Park Condo Apartment for sale (Toronto C09) : MLS®# C12057709
902 33 Jackes Avenue Toronto M4T 1E2
$10,500,000Residential 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 detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
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3403 200 Cumberland Street in Toronto: Annex Condo Apartment for sale (Toronto C02) : MLS®# C12070133
3403 200 Cumberland Street Toronto M5R 0B7
$8,499,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12070133
- Bedrooms:
- 4
- Bathrooms:
- 4
Located in the heart of Yorkville, this luxurious southwest corner suite within the exclusive Yorkville Private Estates offers 3,300 square feet of refined living space with stunning panoramic views to the south and west. Bathed in natural light, the suite features floor-to-ceiling windows, creating a seamless connection to the city skyline. The expansive great room is perfect for both entertaining and relaxing, with the flexibility to customize the space to suit your needs. The gourmet kitchen, equipped with top-tier Miele appliances and ample storage, flows into a cozy family room with access to a private balcony, ideal for enjoying morning coffee or evening meals. A separate office or den, enclosed with French doors, offers a peaceful retreat with westward views. The private bedroom wing includes a spacious primary suite with dual walk-in closets, wraparound windows, and a spa-inspired ensuite with an oversized shower, soaker tub, and dual vanities. The second bedroom, with a sitting area and 3-piece bath, is perfect for guests or live-in staff, while the third bedroom offers a double closet and private en suite. This exceptional suite, in a boutique luxury building, combines space, style, and sophistication in one of Torontos most coveted neighborhoods. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
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68 Rowanwood Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12094739
68 Rowanwood Avenue Toronto M4W 1Y9
$7,999,000Residential 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
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1-6 66 Avenue Road in Toronto: Annex Commercial for sale (Toronto C02) : MLS®# C12002469
1-6 66 Avenue Road Toronto M5R 3N8
$7,500,000 /For SaleCommercial- Status:
- Active
- MLS® Num:
- C12002469
- Major Bus.:
- Medical/Dental
- Total Area:
- 0 sq. ft.
Once-in-a-lifetime investment opportunity. Prime Yorkville medical offices. Location does not get better than this. On the corner of Lowther/Avenue. Six fully tenanted commercial offices/medical offices. Complete first floor with auxiliary storage room in lower level. 12 underground parking spots. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
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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
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269 St Leonard's Avenue in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12) : MLS®# C12148885
269 St Leonard's Avenue Toronto M4N 1K9
$6,098,888Residential Freehold- Status:
- Active
- MLS® Num:
- C12148885
- Bedrooms:
- 6
- Bathrooms:
- 5
Exquisite custom built family residence designed by architect Loren Rose and interiors by Carey Mudford. This beautifully landscaped, chateau inspired home sits on a generous 50 x 150 ft south facing sunny lot. With high ceilings and a gracious center hall layout, the main level features a stunning dining room, elegant living room, mahogany study, gourmet eat-in kitchen and family room with walk-outs to rear stone terrace and garden. The second level features a spectacular primary suite with2 dressing rooms and spa like 6pc ensuite. There are four additional bedrooms with ample closet space and two more bathrooms. The entire lower level features heated floors and has direct access to large attached garage along a walk-out to the rear garden. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
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Data was last updated May 21, 2025 at 04:15 AM (UTC)
Eugene Palermo
Chestnut Park Real Estate Ltd., Brokerage