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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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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
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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
- Contact by Email
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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
- Contact by Email
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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
- Contact by Email
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20 Elm Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12300699
20 Elm Avenue Toronto M4W 1N3
$13,950,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12300699
- Bedrooms:
- 6
- Bathrooms:
- 9
A magnificent and grand Rosedale estate that seamlessly blends modern, state-of-the-art living with historic charm. Set on an extraordinary 80 x 229-foot lot - spanning over 1/3 of an acre - this meticulously restored home offers over 11,500 sq ft of living space across four levels. This elegant residence showcases original architectural flourishes, including hand-carved moldings, eight fireplaces, and a dramatic entrance foyer. Soaring ceilings and intricate details throughout preserve the homes 1890 heritage while incorporating every modern luxury. The home features a huge gourmet kitchen, three outstanding family living areas, spa-inspired bathrooms, and an expansive four-room primary suite. A four-floor elevator ensures effortless access to every level. The backyard is a private urban oasis framed by manicured gardens and offering a magnificent pool and spa, along with multiple terraced patios for entertaining. A gated driveway leads to a detached three-car garage, with parking for up to nine vehicles. Located within walking distance to the TTC subway, top private and public schools, and with quick access to major routes and downtown, this is an unmatched opportunity. A rare chance to own a landmark Rosedale property perfect for grand entertaining and refined daily living. Truly for the most discerning buyer. 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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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
- Contact by Email
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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
- Contact by Email
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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
- Contact by Email
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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 along with EV charger and car wash facility. 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
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205 7 Dale Avenue in Toronto: Rosedale-Moore Park Condo Apartment for sale (Toronto C09) : MLS®# C12223564
205 7 Dale Avenue Toronto M4W 1K2
$7,500,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12223564
- Bedrooms:
- 2
- Bathrooms:
- 3
Welcome to Rosedale's premier boutique building, an incredible feat of architectural design and the ultimate in refined living. This 2 bedroom, 3 bathroom suite with family room offers 2,699 sq ft of impeccable curated interior and the highest craftsmanship finishes. This south-facing suite has floor to ceiling windows with two private terraces overlooking the lush ravine and manicured gardens. The soaring 10-ft smooth ceilings with cove detailing and full height windows welcome natural light throughout the space. The designer kitchen is from Dada Italian kitchens, top-of-the-line integrated appliances, dramatic stone countertop and wall slab backsplash, and custom millwork. Escape to your own private retreat in the primary suite, with a generous sized walk-in closet with custom organizers. The lavish primary ensuite has a deep freestanding tub, shower, water closet, and custom double sink vanity. The second bedroom suite offers its own luxurious feel with ample natural light and 3-piece ensuite of the similar esteemed finishes. Ample storage throughout, separate laundry rm, direct elevator access, and two car parking (1 equipped for EV charging). Pre-wired for motorized window coverings and in-suite sound system, programmable lighting and thermostats, keyless entry, terraces with gas line and water hose bib. This ultra-luxury boutique condo has just 26 residences and is a rare fusion of historic legacy and contemporary design in one of Toronto's most esteemed enclaves. The building has an elegant entrance lobby, bicycle storage room with workshop, multi-purpose room, extensive gym including yoga room, equipment from Peloton and Tonal, infrared sauna, and luxury marble change rooms. Equipped with a state of the art home security system and 24 hr concierge service. This is a location that captures both privacy and convenience, with easy access to fine dining, upscale shopping, walking trails, TTC subway, and the DVP for easy commuting. 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 July 30, 2025 at 04:15 AM (UTC)
Eugene Palermo
Chestnut Park Real Estate Ltd., Brokerage