-
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
-
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
-
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
-
310 Palmerston Boulevard in Toronto: Palmerston-Little Italy House for sale (Toronto C01) : MLS®# C12313549
310 Palmerston Boulevard Toronto M6G 2N5
$12,500,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12313549
- Bedrooms:
- 6
- Bathrooms:
- 7
310 Palmerston Blvd is considered to be the finest historical restoration in the City. The genius of JF Brennan Design creates a grand residence of almost 9,000 sq ft of living space on all 4 levels. The brilliance of this distinctive residence is that it blends unique thinking into an architectural achievement of world class taste and esthetics. Originally built in 1889 the structure was reimagined into four luxury freehold townhouses. Throughout the residence, there is a mix of modern, antique, vintage and bespoke lighting & finishes that create a dynamic atmosphere. As you enter the grand entrance, you are overwhelmed by the soaring ceilings and the unforgettable attention to detail. A pair of industrial steel and glass doors introduces the thematic overture of the home. Every room on the main floor is awe-inspiring and on an immense scale, with ceiling heights of up to 14 feet and floors of travertine stone. The open concept family room and kitchen will be the center of your life. The second floor living space has a primary suite unlike any other - a sitting room with double height focal-point windows and a fireplace, then pocket doors to the bedroom, a marble-rich 6p ensuite, and a custom walk-in closet. The two additional bedrooms are equally special, each with an ensuite. The third floor has a captivating metal frame skylight that transmits an incredible amount of daylight into the home. The lower level has a guest suite with a kitchen and a full bathroom. Elevator, two-car garage with EV charger. There is a private expansive courtyard that is the perfect backdrop for dining and entertaining. This home is inconspicuous from the street and then opens up into a neighbourhood rich with culture and conveniences, with the best that Toronto has to offer. Walk to Little Italy, Kensington, UofT, Queen St, and enjoy all the restaurants and independent shops along College St. 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 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
-
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
-
142 Buckingham Avenue in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12) : MLS®# C12264499
142 Buckingham Avenue Toronto M4N 1R6
$7,395,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12264499
- Bedrooms:
- 5
- Bathrooms:
- 5
Welcome to this exquisite custom-built home, perfectly located in the heart of the highly coveted Lawrence Park neighbourhood. Situated on a sprawling 50 X 150 ft lot, this newly finished 5 bedroom, 5 bathroom home is a triumph of architecture and craftsmanship. The 5300 total square foot residence was crafted with precision and care by Rock Cliff Homes a renowned builder known for unparallelled quality. The state of the art design by mcr interiors exemplifies sophistication from the moment you step inside. Every detail, from the thoughtful layout to the advanced mechanical and tech systems, has been meticulously attended to, resulting in a residence that is truly unrivaled. The main floor stuns with its expansive design, where the formal dining room seamlessly flows into a show-stopping gourmet kitchen featuring top-of-the-line Miele appliances, an oak island and convenient butlers pantry. The adjacent, oversized family room with a gas fireplace and custom built-ins overlooks the spacious backyard deck, creating the perfect backdrop for entertaining. A stunning, private office with sitting area and its own fireplace complete the first level. The incredible primary suite is a sanctuary of comfort, complete with a built in, oak and upholstered King size bed, large walk in closet and a spa-like ensuite. 4 more well proportioned bedrooms complete the 2nd level. One of them currently customized as a 2nd home office. The magazine worthy backyard features a stunning pool and incredible landscaping. The lower level exceeds expectations. The 6th bedroom and extra bathroom work well as potential nanny quarters. The large rec room has tall ceilings and a custom built ins. The theatre room may be the kids favourite room in the entire house. This is Lawrence Park at its best - timeless architecture, intelligent design, and a setting that offers both calm and connection. Fantastic location close to parks, Granite Club and many of the best schools in the city. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
- Contact by Email
-
262 Trillium Place in Simcoe: Rural Innisfil House for sale (Innisfil) : MLS®# N12268812
262 Trillium Place Simcoe L9S 2X7
$5,899,000Residential Freehold- Status:
- Active
- MLS® Num:
- N12268812
- Bedrooms:
- 8
- Bathrooms:
- 6
Luxury waterfront bungalow on Kempenfelt Bay with approximately 125 Feet of shoreline! Introducing a rare opportunity to own a newly constructed, custom-designed bungalow that perfectly blends timeless elegance with modern functionality. Featuring 6+2 bedrooms and 6 bathrooms, this exceptional estate is thoughtfully crafted for multi-generational living, offering both privacy and connection in equal measure. Step inside to an awe-inspiring view of nature and the shores of Kempenfelt Bay, visible from the formal sunken living room - a space that sets the tone for the rest of this remarkable home. The open-concept chef's kitchen seamlessly flows into the dining area and expansive great room with wood-burning fireplace and soaring ceilings, ideal for entertaining or relaxed family living. A purposeful layout that offers comfort and separation for family or guests; one wing has three bedrooms, including the primary suite with built-in desk, walk-in closet, and luxurious spa ensuite. The opposite wing features an additional living room, three more bedrooms, two of which share a Jack & Jill bathroom, plus another full bathroom and laundry room. The lower level boasts two large bedrooms, designer bathroom, a custom gym space, gas fireplace, and luxury vinyl heated floors. With approximately 125 feet of private waterfront, you'll enjoy breathtaking sunsets and the tranquility of life on Lake Simcoe's Kempenfelt Bay. Situated on a rare double lot on a private road with ample parking and an EV charger. The property presents an exceptional opportunity to expand, whether with a sports court or auxiliary structure, the possibilities are endless. Located just 60 minutes from the GTA, combining the peace and beauty of lakeside living with the convenience of city access. From its prime location and sprawling layout to its high-end finishes and stunning waterfront views, this is a one-of-a-kind offering of the very best in luxury, privacy, and lifestyle. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
- Contact by Email
-
102 Mildenhall Road in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12) : MLS®# C12179200
102 Mildenhall Road Toronto M4N 3H5
$5,850,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12179200
- Bedrooms:
- 6
- Bathrooms:
- 7
A truly special residence tucked into one of Toronto's most exclusive and coveted enclaves. Welcome to 102 Mildenhall Road, a timeless and handsome 5+1 bedroom, 7 bathroom home offering over 6,700 square feet of total living space designed for both refined comfort and family functionality. From the moment you step inside, you'll notice the pleasing ceiling height-just over 9 feet on the main level, and the impressive width of the home that enhances the flow and scale of each room. The thoughtful floor plan includes generously sized bedrooms, ensuring no one feels crowded, and beautifully proportioned principal spaces that adapt effortlessly to both formal entertaining and everyday family life. The expansive mudroom is a dream for busy households-fully equipped with custom built-ins, ample closets, and direct access to the spacious two-car built-in garage. The main floor family room is warm and inviting, anchored by a gas fireplace with a classic marble surround, flanked by custom cabinetry for tucked-away storage. On the lower level, you'll find an oversized recreation room perfect for casual gatherings, complete with a wet bar and a dedicated wine cellar with capacity for 94 bottles. A private sixth bedroom with its own four-piece ensuite is discreetly positioned- ideal for a guest suite, nanny quarters, or teen retreat. Just steps to TFS and a short stroll to Crescent School and the Granite club, this home offers an enviable location with easy access to Bayview Avenue and the downtown core via the Bayview Extension. 102 Mildenhall Road is a residence that combines timeless design with the comfort of modern living. This is where elegant living meets everyday ease-ready to welcome your family home. 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 31, 2025 at 12:15 AM (UTC)
Eugene Palermo
Chestnut Park Real Estate Ltd., Brokerage