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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
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- 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
$15,995,000Residential Freehold- Status:
- Active
- 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
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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
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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
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113 Donwoods Drive in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12) : MLS®# C11949548
113 Donwoods Drive Toronto M4N 2G7
$13,588,000Residential Freehold- Status:
- Active
- MLS® Num:
- C11949548
- Bedrooms:
- 5
- Bathrooms:
- 7
Reflecting the grandeur and craftsmanship of times past, with all modern conveniences, this most admired Hoggs Hollow residence enjoys the ultimate privacy against the backdrop of Rosedale golf course. The grand foyer is brightened by a magnificent skylight over a stunning open staircase.The gracious living room lends itself to both formal and casual entertaining overlooking the spectacular, multi- level patios and south garden. Fit for the enthusiastic chef, the kitchen is equipped with custom cabinetry, granite counters, a large island and top of the line appliances. It includes a cozy den and is connected to the elegant, formal dining room.The majestic, two-storey library with rich walnut panelling, fireplace, and wall-to-wall bookcases, features a stately, open staircase leading to a mezzanine and study overlooking the gracious space below. On the west side of the main floor is an enchanting, three-season room with a floor-to-ceiling stone fireplace, an office with three built-in desks, a 3 piece bathroom, and large mud room with built-in cabinets, elevator (to all levels) and direct access to the garage. Upstairs, a private foyer leads to the primary suite with fireplace, balcony, 6 piece marble ensuite. Its exquisite dressing room has floor to ceiling cabinetry and a centre island. Three additional bedrooms with ensuites, and an extra large laundry room complete this level.The lower level adds to the superb entertaining spaces, encompassing a recreation room, party room with wet bar, home theatre, games room, wine cellar, exercise room and 5th bedroom with kitchenette. The family enjoys absolute privacy in the spa-like, south-facing backyard. It includes a naturalized-shaped pool with two rockfalls and a hot tub, surrounded by stunning stone patios and mature, perennial gardens. The expansive, 45' west yard provides a great, child-safe play area and room to add a garden suite or detached garage.Property video on Virtual Tour 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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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 the visionary Joe Brennan who meticulously re-imagined & executed the project, 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, 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®# C11987385
269 St Leonard's Avenue Toronto M4N 1K9
$6,098,888Residential Freehold- Status:
- Active
- MLS® Num:
- C11987385
- 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
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41 Boswell Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C11923117
41 Boswell Avenue Toronto M5R 1M5
$5,995,000Residential Freehold- Status:
- Active
- MLS® Num:
- C11923117
- Bedrooms:
- 4
- Bathrooms:
- 5
Beautifully crafted 3+1 bedroom detached home located in the heart of Yorkville. This stunning property features a quartzite kitchen, a lower-level gym with full-height ceilings, and premium finishes throughout. The interior design blends white oak, quartzite, marble, and brass accents, all meticulously curated during a complete renovation. Tucked away on a quiet cul-de-sac, this home offers a perfect alternative to condo living, combining luxury, style, and comfort. Heated driveway and pathways add both practicality and charm to this remarkable residence. A true Yorkville masterpiece, it delivers a refined yet functional living space that defines modern sophistication. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
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1 Hawthorn Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C11967515
1 Hawthorn Avenue Toronto M4W 2Z1
$5,995,000Residential Freehold- Status:
- Active
- MLS® Num:
- C11967515
- Bedrooms:
- 5
- Bathrooms:
- 4
Welcome to this exquisite South Rosedale Victorian family home, recently renovated while retaining the glorious ceiling height for an abundance of natural light. Created and transformed by the current owners in a very tasteful, cool and high-end contemporary feel and look. A marvellous blend of old meshing with new. The ideal family location for schools, parks, and everything Rosedale has to offer. Enjoy the private in-ground pool with Ipe wood decking and Japanese-inspired landscaping. The outdoor seating area has plenty of room for a separate lounge & al fresco dining area for entertainment & outdoor fun. The garden has a spa-inspired Zen feeling with an abundance of tranquility. Exterior lighting makes this garden even more enjoyable in the evening. The interior is filled with clean lines & high-end finishes. Enjoy the gourmet kitchen which opens to the family room overlooking the pool. The primary bedroom was renovated in 2018 along with the other bathroom on the second floor. The primary is self-contained and sizeable with numerous built-ins and a hidden walk-in closet. The primary suite also contains a contemporary 4-piece marble-clad ensuite. There are another 4 bedrooms & glorious family bath. The third floor is a multi-functional space which can be used as, or converted into anything you can dream up. It also has a 2-piece bathroom already there to expand on. The lower level is finished with a games room, 3-piece laundry and 3-piece bathroom as well as plenty of storage space. Contemporary two-car garage completely re-built featuring live-roof. South fencing completed to match garage at the same time with exterior lighting. A must-see South Rosedale masterpiece. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
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10 Parkwood Avenue in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C12096335
10 Parkwood Avenue Toronto M4V 2W8
$5,800,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12096335
- Bedrooms:
- 4
- Bathrooms:
- 4
Tucked in the heart of Forest Hill, just steps from the village, this refined 3+1 bedroom, 4-bathroom detached home with an elevator offers a serene escape for those who seek peace, light, and thoughtful design. Floor-to-ceiling windows and soaring ceilings fill the home with natural light and airiness, creating a seamless connection between indoors and out. A warm oak-paneled foyer with custom storage and a private elevator sets the tone for the tranquil spaces that follow. The living room, with garden views framed by expansive glass, features a minimalist fireplace and concealed TV, perfect for quiet evenings or effortless entertaining. The Cameo-designed kitchen is equally serene complete with Miele appliances, abundant storage, a waterfall Carrara marble island, and a built-in coffee bar that opens onto a private garden terrace. A sunlit dining room with an east-facing bay window offers the ideal space for intimate gatherings, while a sleek powder room, 10" white oak floors, and integrated speakers enhance the main level's refined flow. Upstairs, the primary suite is a calming retreat, with western light, garden views, a spa-like, 6-piece ensuite offers a deep sense of calm, with an oversized walk-in shower wrapped in Carrara Venatino Marble, & a custom walk-in closet for effortless organisation. Two additional bedrooms, each with floor-to-ceiling windows & peaceful eastern views, share a spacious 5-piece bathroom, making the upper floor a perfect blend of comfort & simplicity. The lower level offers radiant heated floors, a second entrance, garage access, a family room, guest bedroom or gym, full bath, laundry, and generous storage. This home is a rare offering a modern, low-maintenance sanctuary that blends architectural elegance with a zen-like calm. With its luminous interiors, flowing open-concept design, & ample wall space for curated art, its a place to breathe deeply, live mindfully, & feel utterly at home. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
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Data was last updated April 29, 2025 at 06:15 AM (UTC)
Eugene Palermo
Chestnut Park Real Estate Ltd., Brokerage