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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
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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
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
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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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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
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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
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
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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
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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
- 416-925-9191
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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
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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
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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
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
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Data was last updated July 21, 2025 at 06:15 PM (UTC)
Eugene Palermo
Chestnut Park Real Estate Ltd., Brokerage