• 5
• 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. (id:29237)

• 6
• 8

As one of Toronto's original landmark estates, the 'Rosewood Estate' sets the bar for uncompromising luxury in the city. Tucked discreetly at the end of a quiet cul-de-sac, the residence rests on a sprawling 1.12 acre private ravine lot. Reimagined in 2019 by acclaimed architect Lorne Rose, with interiors by Dvira Interiors, and built to exacting standards by JTF Custom Homes, the home is a masterclass in vision, craftsmanship, and enduring design. The approach is cinematic: a stone and wrought iron fence opens to manicured gardens, mature maple trees, and imported European planters that frame the limestone façade and cedar roofline. A heated drive and walkways lead to grounds designed for both grandeur and privacy, where an elegant saltwater pool, cabana, outdoor kitchen, fireplace, and a full sports court are seamlessly woven into the landscape. The gardens dissolve into a lush ravine backdrop, offering rare tranquility within the city. Inside, nearly 12,000 square feet of living space unfolds with quiet confidence. Timeless custom crown moulding and wainscoting, hand-carved marble fireplace mantels, and imported European wallpaper and hardware create a layered, textural narrative throughout. Built-in cabinetry and vanities by Falcon Kitchens anchor the principal rooms, while marble counters, bespoke lighting, custom drapery, and automated blinds reflect meticulous attention to detail. The chef's kitchen is equipped with a suite of luxury appliances, including a La Cornue range, and flows effortlessly into both formal living spaces designed for modern family life. The upper levels offer five serene bedrooms, including a primary retreat with soaring vaulted ceilings, dual bespoke dressing rooms, and a lavish marble-clad ensuite. The lower level rivals a private club, complete with a state-of-the-art theatre, glass-enclosed gym, recreation spaces, a nanny suite, and a large laundry room. Rosewood Estate is not merely a residence, it is a legacy property. (id:29237)

• 6
• 7

This remarkable residence stands apart among Forest Hill's most architecturally sophisticated homes. Designed & lived in by the current owners for their young family, its adaptable 8,345' layout easily accommodates executive lifestyles-from entertaining with ease to family-focused living where the stunning Kit can seamlessly open to the adjoining DR & Fam areas, & the lower media room/play room may be a children's play room or creative studio. Balancing warmth with precision, the interiors evoke serene modernism through tactile finishes & finely measured detail. Pale oak, bronze fixtures, honed limestone, & softly textured surfaces create a natural palette that diffuses light with quiet luxury. Expansive windows frame curated garden views, merging the exquisite interiors with the lush landscape. Featured in design publications, the home, built by Whitehall Homes, embodies elevated craftsmanship, soaring 11' clgs, Venetian plaster, de Gournay, molded & panelled walls, & a circular DR complemented by an elegant cherrywood study. Two offices on the main & a 14' high Library offer exceptional versatility for modern professionals. Thoughtful updates include gallery-grade lighting ('21), a Bloomsbury kitchen with servery & adjoining mudroom ('18/19), refinished rift-sawn oak herringbone floors ('18), & exquisite terraces & gardens by Janet Rosenberg ('17/18). Exemplary appointments include 2 1/4" thick veneered & hand-waxed crotch mahogany doors with custom Nanz hardware, a 31' grand hall anchored by a dramatic 3-floor split staircase, Scalamandré silk-upholstered walls in the Fam Rm, & a sumptuous PR suite featuring a vaulted Atrium Sitting area, dual ensuites with sep dressing zones, & handwoven silk broadloom. A light-filled 28' Hall Sitting area overlooks the grounds & striking Library. The lower provides a 5th & 6th BDRM, a fabulous Media/Play Rm, wine storage, a fitness or yoga studio, lots of storage & Lau. Radiant-heated floors in principal rooms. (id:29237)

• 7
• 9

The Rosedale Grand Estate In the prestigious Bridle Path Sunnybrook York Mills neighbourhood, The Rosedale Grand Estate stands as a testament to timeless grandeur and modern sophistication. Positioned on a southwest-facing ravine lot (106.6 x 306), the residence offers panoramic views of the Rosedale Golf Club and a rare conservation backdrop. A full walk-out design extends to expansive terraces and a resort-inspired pool, creating a seamless connection between elegant interiors and the natural outdoors. With approximately 13,280 square feet of living space across three levels, the estate embodies both scale and refinement. Soaring ceilings, rich hardwood floors, and walls of glass bring light and openness throughout. The principal suite serves as a private retreat with a spa-like ensuite, elegant dressing room, and three walk-in closets. At the homes centre, a custom chefs kitchen with walk-in pantry flows into the grand family room, while the sweeping central hall and curved staircase overlook the ravine, offering an architectural statement of distinction. The full walk-out lower level transforms into an entertainers haven, complete with a home theatre, bar, gym, sauna, and nanny's suite. An elevator services all three levels, ensuring accessibility and ease. Beyond the residence, the lifestyle is unmatched. Families benefit from proximity to some of Canadas most celebrated private and public schools. Just minutes away, downtown Toronto awaits with its world-class dining, cultural attractions, theatres, and luxury shopping. With 6+1 bedrooms and 8 bathrooms, The Rosedale Grand Estate is more than a home it is a statement of legacy, offering privacy, prestige, and connection to the best of Toronto living. An extraordinary residence where conservation beauty, refined luxury, and city sophistication meet. A world of magnificence awaits! (id:29237)

• 6
• 8

106 Glenayr Rd won 2025 Best Luxury Residential Interior Design Ontario and Luxury Lifestyle Award TOP 100 Interior Designers of the World. Highly acclaimed visionary leader Omid Taba OE Design built this significant residence on most exquisite Billionaire's Row. Arrive with your luggage and relax as if you were moving into a Four Seasons Presidential Suite. The pre-arranged luxury is designed for those seeking high-end comfort and turnkey lifestyle. It checked all the well-loved Forest Hill home amenities: *Elegant stone facades.*Appx 8,750 SF sophisticated interior. *3-storey layout with elevator. *6 Ensuite bedrooms incl enormous dressing suites and precious boudoir. *Sumptuous 14' entryway with a top-notch office. *Multiple Lounge Hubs for family gatherings. *Magazine-worthy chef's kitchen with two marvelous waterfall islands, ample pantry and paneled upscale appliances. *3rd & Lower Flr 2-Laundry. *A consistent rich, luxe tone is achieved through trimless shadow reveals and refined textured treatments on all surfaces. Bespoke emerald palette seamlessly balances warm brass accents, white oak planks, and dramatic marble veins. *Comprehensive home comfort plan incl Control4 automation, smart lighting/sound/security, radiant heated floors, zoned heating/cooling, sustainable wellness-focused building materials, and thoughtful engineering allows high ceiling, airy oasis and open to above flows. *Nine skylights and premium wall-to-wall windows provide excessive natural light, complemented by layered architectural lighting throughout. *Sculptural float staircase with biophilia garden. *Resort-like lower level boasts Club Lounge with VIP Home Cinemas and Gym, Opulent Marble Cocktail Bar with illuminated Wine Cellar, Lower walkout to lighted garden, enormous B/I BBQ patio and heated Betz pool.*Tuckaway Nanny Quarter. *3-car Garage with snowmelt drive & walkways. A true timeless masterpiece offers experiential living tailored for the most discreet luxury connoisseurs. (id:29237)

• -
• -

The property features 25 apartment units, including studio, one-bedroom, two-bedroom, and 1 commercial unit, delivering strong current income with clear and achievable upside potential. Investors will benefit from immediate cash flow and the opportunity to enhance returns through strategic rental growth. (id:29237)

• 6
• 10

A rare Forest Hill offering, this custom residence showcases over 8,000 square feet of beautifully finished living space across five levels, all serviced by an elevator. Built in 2017 and extensively refined, the home offers exceptional scale, comfort, and craftsmanship. Grand principal rooms flow seamlessly for both everyday living and entertaining, anchored by a top-tier chef's kitchen, inviting family room, main floor library, dining room, and lounge with custom cabinetry and bar fridges. The second level features a sumptuous primary suite with his/her 3-piece and 5-piece ensuites and separate dressing rooms, along with four additional bedrooms, each with its own ensuite. Designed for complete lifestyle living, the lower level includes a home theatre, glass-enclosed gym, recreation room with bar, large wine cellar, and nanny suite. Outdoor living is equally impressive, with a stunning pool and hot tub, 2-piece washroom off the pool deck and cooking hub. An oversized double garage with pet spa and the convenience of a mud room completes this exceptional home, ideally located near top schools, parks, and local amenities. (id:29237)

• 4
• 5

This extraordinary suite at the Four Seasons Private Residences in Yorkville redefines luxury living in the heart of Toronto. This is not just a residence but an elevated lifestyle reserved for a select few. Created by merging two units into a single masterpiece, the suite spans approximately 5000 square feet with soaring 10' ceilings, presenting the scale and poise of a home in the sky. Enter via two private elevators directly into an elegant foyer of epoxied and honed marble, then step into luminous living spaces framed by floor-to-ceiling windows with sweeping south-west-east unobstructed views and two expansive private terraces.The culinary centrepiece is a chef inspired kitchen featuring custom Kobi cabinetry, two waterfall edge Statuario marble islands and fully integrated Subzero and Miele appliances. Rich walnut and Xorel panels, Moncer custom Herringbone Oak Hardwood flooring and a floating fireplace showcase meticulous design throughout. Four generous bedrooms and five bathrooms - including a primary ensuite with heated floors, Vola plumbing fixtures, honed Calacatta Oro epoxy filled mosaic detailing and large walk in closet - offer sanctuary and luxury in equal measure.Comfort and ambiance are seamlessly managed via two hvac units with concealed returns and linear vents. Residents enjoy world class Four Seasons services: 24/7 concierge, full service spa, valet parking, indoor pool, state of the art gym and wellness centre, room service, house keeping and culinary options include Cafe Boulud and D bar lounge, all in a secure refined environment (id:29237)

• 6
• 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 flagstone 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. (id:29237)

• 6
• 10

A landmark residence in the heart of Forest Hill, masterfully developed and designed by Danieli Development Group, a name synonymous with precision, craftsmanship, and timeless luxury. Spanning approximately 10,000 sq ft across the entire property, this architectural statement blends modern-classical symmetry with refined contemporary interiors. A grand stone façade, formal landscaping, and commanding presence set the tone. Inside, 12-foot ceilings on the main floor and herringbone flooring throughout the entire home create scale and cohesion. The home is serviced by a private elevator and features four fireplaces, including a striking natural stone living room focal point. The chef's kitchen and fully equipped butler's kitchen are appointed with premium Miele appliances, bespoke cabinetry, and natural stone surfaces. Entertain with a custom-designed wine cellar featuring leather accents, wine peg detailing, glass, mirror, and warm wood veneer finishes. The second-floor hallway is defined by mirrored walls that enhance light and depth. The primary suite offers a fireplace, separate his-and-hers walk-in closets, and dual spa-inspired ensuites with steam showers and bespoke finishes. Two additional bedrooms are located on the second floor, with two more on the third level. The lower level offers a private theatre, nanny suite with ensuite, and a resort-inspired wellness retreat. The indoor Sicis saltwater pool with iridescent mosaic tile is complemented by a dramatic double-sided fireplace, along with a bar, heated floors, steam room, and gym. Completing the home is a rare five-car garage, plus a heated two-car driveway, front porch walkway, and rear porch. Currently nearing completion, this residence presents a rare opportunity for the buyer to participate in final design selections and finishing touches. (id:29237)

• 8
• 11

Architecturally Significant Iconic Estate , Situated on Toronto's Most Exclusive & Prestigious Banbury Neighborhood With Walking Distance To Bridle Path Trail. Over 7300 Sqft. Above Grade Luxurious Living Area Plus Over 3000 Sqft. Finished And Walkout Heated Basement, Designed And Crafted By An Acclaimed Architect & Builder. Clad in Indiana Limestone Front Elevation W/Architectural Brick Accents, Enhanced by Lush Landscaping, a Heated Driveway & Dramatic Exterior Lighting. Exceptional Craftsmanship is Showcased Throughout W/Custom Walnut & White Oak Millwork, Imported European Slabs, 12' Ceilings, Elegant Wall Paneling, Detailed Moldings, Heated Floors & Custom Wood Accent Walls. Floor-to-Ceiling Tilt & Turn Aluminum Windows & Sliding Doors, Flood The Home W/Natural Light. The Grand Foyer Features Imported Italian Slabs, a Striking Staircase, And An Oversized Skylight, Setting a Refined & Elegant Tone. Expansive Principal Rooms Highlight Chevron Hardwood Floorings, Gas Fireplaces, And Book-Matched Italian Slab Feature Walls.The Chef-s Kitchen Offers Dual Islands, Top-Of-The-Line B/I Appliances, a Butlers Pantry W/Servery Access to the Formal Dining Room & Custom Cabinetry. The Breakfast Area & Oversized Family Rm. Include Large-Scale Aluminum Sliding Doors Leading to an Expansive Deck & Concrete Swimming Pool. A 4-Stop Elevator Services All Three Levels, Plus an Additional Private Lift W/Direct Garage Access Fully Accessibility-Friendly. The Primary Retreat Boasts Coffered Ceilings, a Wet Bar, Fireplace, Boutique-Style Hers Dressing Boudoir, His Closet, And a Lavish 7-Piece Ensuite Designed to Impress. The Entertainment-Ready Basement Boasts an Oversized Recreation Area W/ 2 Double Aluminum Sliding Doors Offering Garden-Level Views And Abundant Natural Light, a Large Gym W/Washroom and Dry Sauna, a Home Theatre, Additional Washer/Dryer, And Direct Access From the Garage Complete W/a Dog Wash Station & Elevator Access. The Finest in Luxury Amenities! (id:29237)

• 3
• 4

An extraordinary residence in the heart of Yorkville, Suite 1201 at 155 Cumberland offers over4,000 sq. ft. of bespoke living space-a rare half floor home that combines architectural pedigree with modern refinement. With only 15 residences in the building, privacy and discretion are absolute, while the address places you steps from Toronto's finest dining, boutiques, and cultural institutions. This 3-bedroom plus family room residence is defined byits scale and proportion. Ceilings soar to almost 12 feet, while floor-to-ceiling windows frame sweeping city and treetop views. The great room spans the south façade, offering a dramatic yet serene setting for both intimate evenings and grand entertaining. A dedicated dining gallery flows seamlessly into the Downsview-designed chef's kitchen, where top-tier appliances, expansive counters, and custom cabinetry create a space equally suited to culinary artistry and casual gatherings. The primary suite is a private sanctuary, with a spa-inspired ensuite featuring a freestanding soaking tub, walk-in shower, radiant heated floors, and generous dressing areas. Two additional bedrooms, each with an ensuite, provide comfort for family or guests, while the family room offers a second living core-ideal for film, reading, or quiet retreat. Every detail, from wide-plank hardwood to polished stone, has been curated for timeless elegance. Outdoors, a private terrace extends the living space, offering a rare vantage point above Yorkville's storied streets. The building itself is an icon of exclusivity, originally conceived as a modernist penthouse in the 1960s and reimagined in 2010 by KingSettCapital and Quadrangle Architects. Residents enjoy 24-hour concierge, secure underground parking, and discreet entry, ensuring a lifestyle of effortless luxury. Suite 1201 is more thana condominium-it is a trophy residence, offering the scale of a private home with the convenience and prestige of Yorkville's most exclusive address. (id:29237)