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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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18 Chestnut Park Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12410500
18 Chestnut Park Road Toronto M4W 1W6
$13,995,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12410500
- Bedrooms:
- 6
- Bathrooms:
- 7
Architectural Digest quality with a 2-storey coach house/double car garage, circular drive, and parking for 6/7 cars. This home is both grand and completely maintenance-free, with all exterior surfaces heated. The wine cellar with a glass ceiling extends a level below the lower level, and there is a rough-in for a 3-floor elevator. This home was custom designed by architect John O'Connor with incredible attention to detail, including ample storage closets and ensuites with every bedroom. The main floor is centre hall with a large foyer, living room, and dining room. The entire back of main floor is comprised of kitchen, family room, with wood burning fireplace, and attached pantry. There is a 2-piece and an incredible mudroom as well. The 2nd floor primary bedroom is state-of-the-art with ensuite, and his and hers walk-in closets. There is an office/den and guest bedroom with ensuite, and a large laundry room completing this floor. The floating staircase takes you to the 3rd floor, which has 3 bedrooms, each with their own ensuite. The lower level feels like an elegant New York Club with a gas fireplace, custom golf simulator/movie theatre, games area and gym. Outside is a beautiful walled garden and coach house which provides a completely separate 1 bedroom apartment. This home is for the most sophisticated and discerning buyer in the most coveted location. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
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- 416-925-9191
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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
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50 Teddington Park Avenue in Toronto: Lawrence Park North House for sale (Toronto C04) : MLS®# C12364967
50 Teddington Park Avenue Toronto M4N 2C6
$11,995,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12364967
- 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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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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80 Lynwood Avenue in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C12389813
80 Lynwood Avenue Toronto M4V 1K4
$8,495,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12389813
- Bedrooms:
- 6
- Bathrooms:
- 8
In the heart of South Hill, this custom-built limestone home offers more than 7,500 square feet of carefully designed living space with every modern convenience. Designed with scale and functionality in mind, the interiors are filled with natural light, with large principal rooms ideal for entertaining as well as everyday family living.The double-height foyer features integrated closets and heated floors, leading into a wide entrance hall. Formal dining and living rooms are appointed with chevron white oak floors, tray ceilings with recessed lighting, and a gas fireplace. The chefs kitchen offers custom millwork, an oversized pantry and servery, and a curved hood that doubles as a design feature. It flows into the family room with another fireplace and walkout to the landscaped backyard. At its centre is the custom cabana, complete with skylights and a two-piece bath, designed as a private retreat steps from the main home.Upstairs a primary suite with a boutique-style walk-in closet and spa ensuite, five spacious bedrooms and five bathrooms, laundry room and a large sun filled study. Other highlights include a heated driveway and front steps, an elevator, a 12 person theatre, an oversized home gym, and a 1,000+ bottle wine cellar.The garage includes a side entrance and direct access to the mudroom, integrated lighting, mirrored doors, and capacity for a lift.The lower level expands the living space with a large recreation room and walkout to the backyard, an open gym, a guest or nanny suite, a second laundry room, and lots of storage.Every feature has been considered to create a home that balances luxury, comfort, and practicality in one of Torontos most sought-after neighbourhoods. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
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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
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10 Rosedale Road in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12420297
10 Rosedale Road Toronto M4W 2P3
$7,295,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12420297
- Bedrooms:
- 5
- Bathrooms:
- 7
At long last, this grand Edwardian residence in South Rosedale has been completed with perfection by MCR Interiors, offering an exceptional, confident, and fully custom luxury home within walking distance to both Yonge Street and Yorkville. Interiors encapsulate nearly 4000 square feet above-grade with over nine foot ceiling heights on all levels, and offer completely custom, completely new, and completely luxurious interiors. Curated finishes include heated marble floors with herringbone inlays, a beautiful assembly of formal and informal spaces on the main floor, and practical and coveted features such as a large mud room with direct access to the two-car garage. The kitchen is of course completely customized with dove-tailed wooden cabinetry and outfitted with an oversized, top-of-the-line integrated appliance package. A pretty window seat overlooks Rosedale Road, and an amazing walk-in pantry satisfies the practical needs of such a functional kitchen. The home is enlarged by a three-storey glass addition that marries the historic front facade with a modern and exciting rear exterior. On the second floor the addition houses a study or home office, and on the third floor, a children's lounge area for homework or a separate media space. All bedrooms are equipped with individualized ensuite bathrooms. The primary bedroom is most exceptional with incredible proportions, a huge walk-in closet with LED and glass inlays, and an exquisite five-piece ensuite. A large terrace on the second floor is accessed from the primary suite, with a quiet perch above Pine Hill Road and Rosedale Road and cascading views down to Branksome Hall's soccer pitch. The basement was lowered and underpinned and now holds ceiling heights reaching 9'4". It houses a huge recreation space, nanny suite, separate powder room, and a gorgeous walk-in laundry room. This home's versatility can appease families (literally steps to Branksome Hall), or "downsizers" not ready for condo living. A must see! More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
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14 Banbury Road in Toronto: Banbury-Don Mills House for sale (Toronto C13) : MLS®# C12350266
14 Banbury Road Toronto M3B 2K4
$6,988,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12350266
- Bedrooms:
- 3
- Bathrooms:
- 5
An Exquisite French-inspired residence in the Bridle Path. This exceptional home blends timeless elegance with modern luxury, showcasing masterful craftsmanship and meticulous attention to detail. Grand principal rooms adorned with intricate millwork, soaring ceilings, and sun-filled spaces designed for both gracious entertaining and everyday living. This home is a masterpiece of design, featuring ornate and timeless wall panelling and curated designer finishes that exude sophistication. The chefs kitchen is a work of art, boasting custom cabinetry and premium appliances. Retreat to the primary suite, a sanctuary of indulgence with extensive closet space and a marble-clad ensuite. Full lower level with a recreation room, second kitchen, additional guest space, exercise room, and storage rooms. The backyard is superb - with a covered outdoor loggia, terrace and extensive patio space for relaxing and entertaining - complete with an inground swimming pool. Plus a fantastic gazebo and 3-piece washroom. The property is completely landscaped: stone paver driveway and walkways, gated front entrance, with an emphasis on privacy from the street. This palatial home is set in one of Toronto's most exclusive neighbourhoods, with conveniences and recreational amenities in the immediate vicinity. This residence offers a seamless blend of old-world grandeur and contemporary comfort, offering a rare opportunity to live such a refined lifestyle. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
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43 Summerhill Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12435149
43 Summerhill Avenue Toronto M4T 1A9
$6,895,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12435149
- Bedrooms:
- 5
- Bathrooms:
- 5
Fabulous, custom, and sophisticated Midtown home in Summerhill! This stunning residence offers stylish living throughout featuring hardwood floors and floor-to-ceiling windows. The main floor includes a powder room and an open-concept kitchen equipped with a built-in banquette, a centre island that doubles as a breakfast bar, and top-of-the-line appliances. A walk-through pantry complete with built-in cupboards and a sink connects the kitchen to the dining room. The main-floor family room opens onto a private garden, which leads to a heated double garage with an EV charger, accessible via a laneway. Upstairs, you will find three spacious bedrooms, each with its own ensuite and walk-in closet featuring built-ins. The luxurious primary suite offers a walk-in closet with custom built-ins, additional wall-to-wall closets, and a 5-piece spa-like ensuite with a custom Toto toilet and steam bath. The second-floor laundry room is equipped with a front-load washer and dryer, laundry sink, and built-in cupboards. The third floor is truly magical, featuring a versatile great room perfect as a custom gym or entertaining space, with a walkout to a large rooftop deck offering stunning city views. Also on this level: a bedroom and a 3-piece semi-ensuite. The lower level includes a state-of-the-art theatre room, wet bar, 3-piece semi-ensuite, and an additional bedroom with a walk-in closet. This home is fully automated with a Control4 System managing lighting and window coverings. Enjoy proximity to TTC, top private and public schools, fabulous restaurants, food and fashion shopping, and parks. This is your perfect home in the most ideal location! More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
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4 Maple Avenue in Toronto: Rosedale-Moore Park House for sale (Toronto C09) : MLS®# C12384091
4 Maple Avenue Toronto M4W 2T6
$6,295,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12384091
- Bedrooms:
- 16
- Bathrooms:
- 10
A rare opportunity in prestigious South Rosedale. This unique sixplex spans over 9,000 sq. ft. with one legal address (4 Maple Ave) and two municipal addresses (4 Maple Ave & 43 Elm Ave). Configured as two conjoined buildings, it offers exceptional flexibility for investors, multi-generational living, or conversion to a luxury single-family residence. With six spacious suites, soaring ceilings, private outdoor spaces, and elegant period details, the property blends character with strong income potential. 43 Elm is vacant, providing immediate opportunity for luxury redevelopment, boutique leasing, or owner occupation. Steps to Branksome Hall, ravines, parks, Yonge St. shopping & dining, plus easy access to Sherbourne, Castle Frank, and Rosedale subway stations. Yorkville is just a short walk via the Glen Road Bridge. Offering the perfect balance of prestige, space, location, and income, this is a one-of-a-kind asset in one of Toronto's most sought-after neighbourhoods. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- EUGENE PALERMO
- CHESTNUT PARK REAL ESTATE LTD., BROKERAGE
- 416-925-9191
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262 Trillium Place in Innisfil: Rural Innisfil House for sale : MLS®# N12268812
262 Trillium Place Innisfil 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
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Data was last updated October 15, 2025 at 12:15 AM (UTC)
Eugene Palermo
Chestnut Park Real Estate Ltd., Brokerage