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An Architectural Masterpiece Of Distinction, Elegance & Enduring Luxury, Gracefully Positioned Within Toronto's Most Prestigious Bridle Path Enclave. Designed Without Compromise, This Magnificent Estate Showcases Grand-Scale Living, Extraordinary Craftsmanship & Bespoke Finishes Throughout. A Breathtaking 21ft. Cathedral Foyer, Elevator Servicing All Levels, Exquisite Quarter-Sawn White Oak Herringbone Floors, Heated Marble Flooring, Intricate Custom Millwork & Designer-Appointed Interiors Create An Unforgettable First Impression. The Spectacular Chef's Custom Made Kitchen Is A Culinary Showpiece, Beautifully Appointed W/A La Canche Gas Range, Premium Miele, Wolf & Sub-Zero Appliances, Custom Cabinetry & An Expansive Entertainer's Island.The Lavish Primary Sanctuary Is The Epitome Of Sophisticated Living, Offering Separate Boutique-Style His & Hers Dressing Rooms & An Opulent Spa-Inspired 9-pcs Marble Ensuite. Each Additional Bedroom Enjoys Its Own Luxurious Ensuite, Ensuring The Ultimate Comfort & Privacy For Family & Guests. The Exceptional Lower Level Rivals The Finest Private Clubs, Featuring A State-Of-The-Art Home Theatre, Elegant Recreation Lounge, Designer Wet Bar, Climate-Controlled Glass Wine Cellar, Fitness Studio, Guest Suite & Walk-Up Access To The Grounds. Beyond The Interior Lies A Truly Resort-Inspired Outdoor Sanctuary. Impeccably Landscaped & Designed For World-Class Entertaining, The Private Backyard Features A Spectacular Inground Swimming Pool, Spa Jacuzzi, Elegant Poolside Cabana, Fully Appointed Outdoor Kitchen, Dedicated 3-pcs Pool Washroom & Private Change Room, Delivering An Unparalleled Lifestyle Of Leisure, Luxury & Sophisticated Outdoor Living.

39 Arjay Crescent, Toronto

Listing courtesy of RE/MAX REALTRON BARRY COHEN HOMES INC..

$10,795,000

5 Beds ⋅ 8 Baths ⋅ C13800356 MLS® #

Masterfully envisioned by renowned Laith El-Bahrani in 2024, the iconic Infinity House stands as a pinnacle of high-performance modern architecture. Inspired by Mies van der Rohe Pavilion, it celebrates high-end modernism, forward-thinking minimalism, and a strategic expansion of horizontal and vertical space. A mindful Pearl Design and AVE Group's whole-building-approach unites flawless move-in-ready luxury with structural intelligence & sustainability. A bronze and limestone envelope unfolds appx 7,684 sf of finely crafted space across three levels with 4+1 beds, 8 baths, a private elevator & heated 2-car garage. Curated with an optimized-ultra-tight structure and net-zero-ready tech, it offers triple-pane glazing, flush baseboards with reveal, Fibonacci roof stone geometry, mid-band metal trough, advanced heat-pump and acoustic insulation, smart home control, heated floor & snowmelt. Main level unveils a majestic entry gallery with a marble slab fireplace, bespoke slat wall, office/library and mudroom. A Chef's Culinary Atelier boasts a sculptural multi-tier quartzite island, Miele/SubZero Suite & a walk-through Pantry & Servery Hall. An ultimate rear NanaWall seamlessly blends nature with private oasis, serene Zen garden, grand hosting terrace, heated pool & subterranean storage. Floating stairs rise elegantly via a soaring limestone wall, premier glass enclosure & skylights to upper Four-Seasons-Hotel-Caliber sanctuary with 4-ensuite and dedicated laundry. Lower Entertainment Wing anchors a wellness hub with gym & steam spa, upscale media lounge with wet bar & wine cellar, and a nanny suite with 2nd laundry. Vast on a 50x184.75 ft premium lot in prestigious Teddington Park, it spans entire block for dual-street access at Teddington Park & Glen Echo Rd, harmoniously refines quiet luxury with excellent walkability to Elite Schools, TTC Subway, Riverview Dr Ravine, Granite Club, Rosedale Golf Club and Yonge St Experience defining an elevated urban lifestyle.

50 Teddington Park Avenue, Toronto

Listing courtesy of SOTHEBY'S INTERNATIONAL REALTY CANADA.

$10,495,000

5 Beds ⋅ 5 Baths ⋅ C14095932 MLS® #

Welcome to 442 Heath Street East, an architecturally distinctive contemporary residence offering more than 6,000 square feet across three levels in coveted Bennington Heights, with interiors by Ashley Botten. Set on an extraordinary lot, this sun-filled home pairs luxurious finishes, thoughtful built-ins, in-floor heating throughout and a heated driveway for year-round comfort. A sleek and stunning entryway features extensive storage and introduces the elegant living and dining room, complete with show-stopping floor-to-ceiling windows. The stunning modern kitchen features a large island and adjoining breakfast area. The expansive family room overlooks the landscaped backyard, while a main-floor office, powder room and attached garage add everyday convenience. Upstairs are four spacious bedrooms, a family library and laundry room, including a spectacular primary retreat with backyard views, a skylit walk-in closet and luxurious five-piece ensuite. The lower level offers a generous recreation room, fifth bedroom, full bathroom, fitness and Pilates studio, infrared sauna and ample storage. And then there is the backyard, which is reminiscent of the most exclusive resorts in the world. Discover a gorgeous swimming pool, expansive entertaining patio, outdoor cooking area, children's play treehouse, butterfly garden, outdoor table tennis and additional green space beyond the pool. Expansive windows bring exceptional natural light into the home and frame its lush surroundings. Enjoy proximity to Moore Park Ravine, the Beltline Trail, Evergreen Brick Works, parks and Bayview Avenue's shops, cafés and restaurants. Nearby schools include Bennington Heights Elementary, Bessborough Drive Elementary and Middle School and Leaside High School (subject to school board policies), with convenient TTC connections, access to downtown and the Don Valley Parkway. A rare blend of modern architecture, family comfort and resort-inspired outdoor living, this home is truly exceptional.

442 Heath Street E, Toronto

Listing courtesy of ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM.

$10,450,000

6 Beds ⋅ 7 Baths ⋅ C13782120 MLS® #

Designed by renowned architect Stan Makow & Associates, 22 Brookfield Road offers approximately 9,882 sq. ft. of total living space on an exceptional ravine lot in prestigious Hoggs Hollow. Thoughtfully designed for both formal entertaining and comfortable family living, the residence combines timeless architecture, generous proportions, and a rare connection to nature in the heart of Toronto. The limestone and brick exterior opens to a resort inspired outdoor setting with a pool, pool house, covered terrace, and views into the surrounding valley landscape. The backyard feels private and protected, with mature trees creating a natural backdrop that is difficult to replicate in the city. Inside, expansive principal rooms, soaring ceilings, an elevator, five fireplaces, and beautifully proportioned living spaces create a refined and livable atmosphere. The residence features 5+1 bedrooms, 7 washrooms, generous family and recreation areas, and a layout that supports both everyday comfort and larger scale entertaining. Hoggs Hollow is one of Toronto's most distinctive residential enclaves, known for its winding streets, estate properties, ravine setting, and quiet country like character within the central part of the city. The neighbourhood offers a rare balance of privacy, land, and access. Ideally located an eight-minute walk from York Mills Subway Station, close to Highway 401, Yonge Street, private clubs, shopping, dining, and everyday amenities. Near many of Toronto's most respected schools, including Crescent School, Havergal College, Toronto French School, and highly regarded public schools. A rare opportunity to own a substantial custom residence in one of Toronto's most established and naturally beautiful neighbourhoods.

22 Brookfield Road, Toronto

Listing courtesy of SOTHEBY'S INTERNATIONAL REALTY CANADA.

$10,398,000

7 Beds ⋅ 7 Baths ⋅ C13862730 MLS® #

A true architectural statement in the best pocket of Lytton Park, 239 Cortleigh Boulevard is an extraordinary 5-bedroom, 7-bath residence conceived by renowned architect Lorne Rose. Spanning 7,565 sq ft of meticulously finished living space, this exceptional home pairs sophisticated design with exceptional craftsmanship and an uncompromising level of detail. A heated limestone driveway and walkway leads to an impressive limestone facade and grand entrance, where heated white marble floors, custom stonework, velvet paneling, mirrored surfaces and brass accents establish an atmosphere of understated opulence. The formal dining room is anchored by a dramatic marble fireplace and built-in marble wine wall. At the heart of the home, the bespoke kitchen showcases a substantial marble island, matching countertops and backsplash, Lacanche range, Sub-Zero paneled refrigerator and freezer, Miele appliances and a generous butler's pantry. The adjoining family room features a custom marble fireplace wall and 12-foot sliding glass doors that open to a heated covered terrace complete with outdoor kitchen. Beyond lies a spectacular private retreat with limestone patio, irrigated gardens and custom concrete pool with waterfall and hot tub. Upstairs, the luxurious primary suite offers bespoke millwork, marble gas fireplace and wet bar, complemented by a spa-like ensuite with heated white marble floors and walk-in spa shower. Two walk-in closets feature custom cabinetry, a backlit onyx island and dedicated Onyx makeup station. Four additional bedrooms each offer beautifully appointed ensuite baths, heated floors and designer finishes. The lower level is designed for effortless entertaining, with a home theatre, sophisticated marble bar, full-size gym, cabana-style change room with direct pool access, nanny suite and secondary laundry. A remarkable offering where architecture, design and resort-style living come together in one of Lytton Park's most coveted homes.

239 Cortleigh Boulevard, Toronto

Listing courtesy of FOREST HILL REAL ESTATE INC..

$10,180,000

5 Beds ⋅ 7 Baths ⋅ C13603996 MLS® #

39 Burton Road is a landmark residence, gracefully positioned within one of the most exclusive and prestigious enclaves in Forest Hill. Set on a rare 100x170.5 FT lot, this extraordinary estate offers appx 5,982 SF above grade plus partially renovated lower level, presenting a remarkable opportunity for both luxury living and scarcity investment. The expansive 17,000 SF grounds are nestled with a dense canopy of mature trees and exquisitely landscaped gardens that provide a private and sensational oasis. Approved severance allows two premium lots, effectively transforming one prominent residence into two and maximizing land value on one of the finest streets. The current mansion was built for an exceptional luxurious lifestyle that balances sumptuous entertaining and personal relaxation. Indulgence recreational amenities highlight an indoor saltwater pool, a circular hot tub, and a sauna that opens to a serene alfresco retreat for maximum comfort and wellness. Originally a Georgian, the mansion was reimagined by acclaimed architect Stanley Shenkman and interior designer Robert Dirstein into an epic modernist statement, defined by bold geometry, sweeping curves, and flat rooflines. Recognized for its distinctive aesthetic, once-famous black-changing-to-white exterior, the residence became a design icon after the radical redesign. Today, the home reflects a celebrated eclecticism and modernism, starring a teak paneled foyer, retro mid-century details, wall-to-wall windows and extensive use of skylights that bathed interiors with natural light. This excellent location is also known for its extreme proximity to walkable social hubs, places of worship, and top-tier schools such as UCC, BSS, Holy Rosary, St Michael's, Robbins, Bialik, Leo Baeck, Forest Hill CI and more. Rich in architectural significance and cultural character, the legendary residence is a rarity offering in a highly coveted row renowned for its affluent scale, influential prestige, and enduring grandeur.

39 Burton Road, Toronto

Listing courtesy of SOTHEBY'S INTERNATIONAL REALTY CANADA.

$10,000,000

5 Beds ⋅ 7 Baths ⋅ W13753906 MLS® #

Leave the city in the city. This serene estate invites you to do just that. Nestled behind the gates on one of Toronto's most exclusive streets, 25 North Drive is a rare architectural offering: a quiet, confident statement where design, art, and nature coexist in harmony. Thoughtfully reimagined through an internationally acclaimed renovation by Reflect Architecture and featured in leading architectural and design publications. Executed with masterful precision, the transformation celebrates both innovation and restraint, elevating everyday living to an art form. At the heart of the home lies a truly exceptional Obumex kitchen, handcrafted in Belgium. This kitchen thoughtfully integrates artful sensibilities, natural inspirations and family-oriented functionality. With minimalist lines and bespoke finishes, this space is more than a kitchen, it is a sculpture in daily use. Expansive windows frame ravine views and infuse the interiors with natural light. The main floor is tailored for elegant living, featuring sun-filled rooms, with an inviting family room, and that stunning kitchen which opens seamlessly to the lush backyard. The upper levels include an expansive primary wing with dual dressing rooms, a spa-inspired ensuite, and treetop views. Four additional bedrooms offer ensuite baths, providing privacy and independence for family or guests. The lower level features a gym, recreation room, kitchenette, and full bath, making it ideal for wellness and entertaining. Manicured gardens, mature trees, a ravine backdrop, a sparkling pool, and a private tennis court elevate the everyday. With architectural pedigree, natural beauty, and a legacy of care, 25 North Drive is more than a home. It is a lifestyle defined by privacy, presence, and permanence. Some homes are built for living, this one was crafted for a life well lived.

25 North Drive, Toronto

Listing courtesy of ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM.

$10,000,000

6 Beds ⋅ 8 Baths ⋅ C13689350 MLS® #

Nestled on a quiet, tree-lined street in Lytton Park, 207 Strathallan Blvd is a bespoke 5+ bedroom residence offering over 6,500 sq.ft. of elegantly crafted total living space. Built in 2019 by Teddington Homes & realized with uncompromising craftsmanship & a refined palette of luxury materials, the home was conceived under the architectural direction of Limor Benmor-Mizrahi (formerly of Peter Higgins Architect) & finished with interiors by Debra Salmoni, embodying a balance of modern sophistication & enduring comfort. A monumental front door opens into a refined foyer with a custom marble-inlay floor. A powder room is conveniently located off the foyer, across from the executive office. White oak & heated stone flooring, soaring ceilings & abundant natural light create an atmosphere of calm refinement. At the front, the executive office is anchored by a sleek see-through gas fireplace that also serves the open-concept formal living & dining areas, where French doors walk out to a flagstone terrace. The centre hall leads into the sun-filled family room with floor-to-ceiling windows & oversized sliders extending the space to the backyard. The south-facing breakfast area enjoys another walk-out. The kitchen, both a design statement & a culinary workspace, features integrated pro-grade appliances, custom Bellini cabinetry, marble countertops & backsplash, an oversized limestone island with seating, extended-height cabinetry & a fully outfitted butler's pantry with access to the mudroom & garage. Upstairs, the primary suite is a private retreat with a gas fireplace, balcony, soaring ceiling & spa-inspired 5pc ensuite. Three additional bedrooms each offer a private ensuite & custom walk-in closet. The 3rd level provides a flexible 5th bedroom suite with a 3pc ensuite & balcony. The lower level features a large entertainment room with kitchenette & walkup, a glass-enclosed fitness studio, a 6th bedroom with 3pc ensuite, the main laundry room, a 2pc bath & a cold room.

207 Strathallan Boulevard, Toronto

Listing courtesy of ROYAL LEPAGE SIGNATURE REALTY.

$9,995,000

6 Beds ⋅ 8 Baths ⋅ C14108620 MLS® #

Situated on one of Forest Hill's most prestigious & sought-after streets, this extraordinary custom-built estate exemplifies luxury living at its finest. Showcasing timeless architecture, impeccable craftsmanship & premium finishes t/out, the residence offers over 8,300 sq. ft. of elegant living space designed for both grand-scale entertaining & refined everyday living. Defined by soaring ceilings, expansive principal rooms & abundant natural light, every detail has been thoughtfully curated to create a sophisticated yet welcoming atmosphere.The home features 6 spacious bdrms & 9 luxurious bathrms, along w/ a rare 1,729 sq. ft. underground garage accommodating up to 5 cars, plus additional heated driveway parking for 2 cars. The main level is tailored for entertaining & family living, featuring a refined private study, formal living & dining rms, & a chef-inspired kitchen w/ premium appliances, custom cabinetry & an oversized breakfast area overlooking the beautifully landscaped backyard. The expansive family rm opens seamlessly to a large deck, creating exceptional indoor-outdoor flow. The 2nd level is highlighted by a luxurious primary retreat complete w/ a private balcony, spa-inspired ensuite & expansive his-&-hers dressing rms. Three additional generously sized bdrms, each w/ their own ensuite bathrm, provide exceptional comfort & privacy. The 3rd level offers versatility w/ a substantial gym & spa retreat, extensive storage & an additional ensuite bdrm ideal for guests. The lower level is designed for entertainment & lifestyle, featuring a stunning home theatre, recreation rm, nanny's room, custom wine cellar & mudrm w/ direct access to the underground garage. Set on a mature, professionally landscaped lot, the private backyard oasis features a salt water swimming pool, multiple entertaining areas & complete privacy. Ideally located near Forest Hill's shops & restaurants, top private & public schools & convenient access to downtown Toronto.

215 Dunvegan Road, Toronto

Listing courtesy of HARVEY KALLES REAL ESTATE LTD..

$9,980,000

6 Beds ⋅ 7 Baths ⋅ C13716682 MLS® #

An Exceptional Custom-Built Stone Residence In Toronto's Prestigious Bridle Path, Set On A Magnificent 100' X 133.79' South-Facing Lot. Offering Over 8,000 Sq.Ft. Of Luxurious Living Space, This Remarkable 5+1 Bedroom, 7-Bathroom Home Combines Timeless Architecture, Exceptional Craftsmanship & Refined Elegance. Sun-Filled Interiors & Expansive Windows Create An Abundance Of Natural Light Throughout. Grand Principal Rooms Showcase Exquisite Millwork, Extensive Crown Mouldings, Elegant Ceiling Details & Fine Finishes. The Gourmet Falcon Kitchen Is Designed For Both Elegant Entertaining & Comfortable Family Living. An Elevator Provides Convenient Access Between Levels, Complemented By Heated Floors, Built-In Speakers, Multiple Fireplaces & Security Camera System. The Expansive Finished Walk-Out Lower Level Offers Outstanding Recreation & Entertainment Space, Complete With A Private Wine Cellar & Direct Access To The South-Facing Grounds. Rare 3-Car Tandem Garage & Generous Private Driveway. Ideally Situated Near Edwards Gardens, Sunnybrook Park, The Granite Club, Toronto French School & Some Of Toronto's Top Private Schools, With Convenient Access To Bayview, York Mills & Hwy 401. An Extraordinary Opportunity To Own A Distinguished Custom Estate In One Of Toronto's Most Coveted Neighbourhoods.

9 Saintfield Avenue, Toronto

Listing courtesy of SMART SOLD REALTY.

$9,980,000

6 Beds ⋅ 9 Baths ⋅ C12833200 MLS® #

Unrivalled luxury defined by exquisite finishes and timeless design. This breathtaking residence features a limestone façade, slate roof, and heated driveway, set on a south-facing 70 ft frontage lot in the heart of prestigious Lawrence Park. Offering approximately 6,400 sq ft above grade plus an additional 3,500 sq ft lower level (as per builder's plans), this home showcases exceptional craftsmanship throughout. Designed by renowned architect Richard Wengle, the residence blends elegance and functionality. The chef-inspired kitchen features custom built-ins, top-of-the-line appliances, a walk-through pantry, and a bright breakfast area, seamlessly opening to a spacious family room ideal for entertaining. A private office with walkout leads to a beautifully landscaped backyard terrace and resort-style yard with swimming pool. A functional mudroom with a separate side entrance adds everyday convenience. A private elevator provides access to the second floor, featuring 5 spacious bedrooms, including a luxurious primary suite with his-and-hers walk-in closets and a spa-inspired ensuite. All bedrooms are complete with their own ensuite bathrooms, along with a sun-filled lounge/work area. The fully finished lower level offers radiant heated flooring throughout, a recreation room, kitchenette/wet bar, gym, theatre, wine cellar, and a guest/nanny suite with walk-up access to the backyard oasis, complete with pool and waterfall feature. Additional highlights include a heated driveway and front steps, and a fully integrated Crestron home automation system.

33 Stratheden Road, Toronto

Listing courtesy of RE/MAX REALTRON BARRY COHEN HOMES INC..

$9,950,000

9 Beds ⋅ 11 Baths ⋅ C14111298 MLS® #

You Feel the Scale Before You Even Understand It. The Depth of the Lot. The Width of the View. The Distance Between You and Anything Else. By The Time You Reach the Front Door, It's Clear This Isn't Just Another Large Home. This Is Land, Presence, and Opportunity Coming Together in a Way That's Becoming Almost Impossible to Find. Set on 1.25 Acres (110.38 X 506.04 Feet), Backing Onto a 15 Acre Golf Course, 23 Bayview Ridge Offers A Level of Openness and Privacy That Defines True Exclusivity. No Rear Neighbors. Expansive Green Space. Skyline Views in the Distance. It's the Kind Of Setting That Quietly Separates Itself From Everything Else on the Market. The Home Spans Approximately 12,000 Square Feet, Built With Solid Concrete and Reinforced by a Distinctive Zig Zag Steel Structure Giving It Not Just Scale, but Substance. This Is a Property That Was Built With Long Term Vision in Mind. Arrival Is Just as Intentional. A Circular Driveway and Parking for Up to 22 Vehicles, Along With a Fourth Garage, Create a Sense Of Capability That Goes Beyond Everyday Living. It's Designed to Accommodate More More People, More Moments, More Possibilities. Inside, 9 Bedrooms and 11 Bathrooms Provide the Foundation, but the Real Value Lies in What Can Be Done Next. The Home Is Nearing Completion, Offering A Rare Window for a Buyer to Step in and Define the Final Product To Shape the Finishes, the Atmosphere, and Ultimately, the Identity of the Space. Because at This Level, It's Not Just About What Exists It's About What It Can Become. Properties With This Kind of Lot, This Kind of Build, and This Kind Of Positioning Are Limited. And Once They're Complete, the Opportunity to Influence Them Disappears. 23 Bayview Ridge Is Not Just a Finished Home-It's a Chance to Take Something Already Significant, and Make It Truly Exceptional.

23 Bayview Ridge, Toronto

Listing courtesy of THE AGENCY.

$9,895,000

5 Beds ⋅ 7 Baths ⋅ C13762956 MLS® #

An extraordinary custom residence by renowned architect Richard Wengle, set on one of Lytton Park's most coveted streets. Ideally positioned on prestigious Lytton Boulevard, this exceptional 50 x 135-foot property offers more than 7,500 square feet of living space, with 4+1 bedrooms and seven bathrooms. The home pairs Richard Wengle's architectural vision with exceptional craftsmanship, dramatic proportions and resort-inspired amenities. Soaring 11-foot ceilings on the main and lower levels, 10-foot ceilings upstairs, floor-to-ceiling windows and white oak hardwood create a sense of warmth and understated grandeur. A sculptural curved staircase, arched glass doors, refined millwork and micro-cement finishes showcase the home's bespoke detailing. Designed for both family living and entertaining, the principal rooms flow effortlessly together. The oversized dining room features a custom built-in bar and concealed entrance to the servery, kitchen and pantry. The primary suite features custom his-and-hers walk-in closets and a heated-floor ensuite. The second floor also hosts a beautifully appointed home office, framed by striking arched glass doors, offering an elegant and private workspace. The lower level offers a private wellness retreat with a state-of-the-art gym, spa, indoor hot tub, steam room, massage room and spectacular 750-bottle wine cellar. Thoughtfully integrated throughout the residence, Sonos audio and Control4 home automation add another layer of comfort and convenience. A covered outdoor patio with skylight, built-in speakers, heaters and barbecue extends the living space outdoors. A fully finished and heated two-car garage, heated floors in the foyer and lower level, and a heated driveway and walkway complete this exceptional offering. Architecturally significant, beautifully crafted and exceptionally complete, this residence offers a rare combination of scale, sophistication, privacy and resort-calibre amenities in the heart of Lytton Park.

424 Lytton Boulevard, Toronto

Listing courtesy of HARVEY KALLES REAL ESTATE LTD..

$9,880,000

8 Beds ⋅ 8 Baths ⋅ C13864318 MLS® #

Nestled in Toronto's prestigious Rosedale neighbourhood, this landmark mansion occupies an expansive 100' x 122' estate-sized lot and offers over 7,500 square feet of impeccably designed living spaces. With 7 + 1 generously proportioned bedrooms, 8 bathrooms, and an exceptional third-floor loft, this grand residence seamlessly blends historic architecture with the scale, elegance, and functionality. Originally built circa 1900 for the distinguished Applegath family, the home has been meticulously restored and thoughtfully maintained to preserve it's architectural heritage including a self portrait stain glass window of Mrs. Applegath herself. Drawing inspiration from the classical traditions of Italian Renaissance architect Andrea Palladiio - most notably his iconic Villa Rotunda in Vicenza, Italy - the home reflects timeless design and exceptional craftmanship. A majestic octagonal central hall, framed by twelve lonic columns, creates an unforgettable first impression and sets the tone for the rest of the residence. Throughout the home, rich period details abound: original oak hardwood floors, finely hand-craved oak mouldings and wainscoting, intricate millwork, and 6 fireplaces with decorative tile and brick hearths. The soaring 10-foot ceilings are adorned with ornate plaster crown mouldings, ceiling medallions, and oak-beamed details that speak to the home's historical significance. Expansive bow windows and beautifully preserved stained glass flood the interior with natural light and highlight the warm, elegant atmosphere. Outside, the property is a private oasis, surrounded by mature trees, lush landscaping, and tranquil gardens that offer rare serenity in the heart of the city. A detached two-car garage and additional parking for three vehicles provide added convenience. This is a once-in-a-generation opportunity to own a truly iconic Rosedale residence - an architectural treasure steeped in history and timeles

114 Glen Road, Toronto

Listing courtesy of HARVEY KALLES REAL ESTATE LTD..

$9,800,000

8 Beds ⋅ 13 Baths ⋅ C13847788 MLS® #

A Truly One-Of-A-Kind Gated Legacy Residence, Thoughtfully Designed And Built To Be Treasured From Generation To Generation. Accessible Through Three Gated Entrances, This Sprawling Estate Offers Approximately 13,000 Sq. Ft. Of Luxurious Living Space, With Eight Bedrooms And Thirteen Bathrooms. A Grand, Bright And Airy Foyer Creates An Impressive First Impression, While A Dramatic Two-Story Bay Window Floods The Interior With Natural Light. Exceptional Craftsmanship Is Showcased Throughout With Exotic Materials And Natural Stone Finishes In The Kitchen And Bathrooms. A Private Second-Floor Suite Provides Ideal Accommodation For Extended Family, In-Laws Or Guests And Features Its Own Bar With Illuminated Shelving And Custom Cabinetry. An Elevator Provides Convenient Access Throughout The Residence. The Lower Level Is Designed For Exceptional Living And Entertaining, Featuring A Private Home Theatre, Wine Cellar, Beauty Room With Sink, Multiple Walk-In Closets For Luxury Collections, And An Impressive Billiards And Smoking Lounge With Custom Cigar-Display Cabinetry. The Private Backyard Showcases A Massive In-Ground Pool Surrounded By A Stone Patio, Complete With An Outdoor Kitchen And Spacious 800 Sq. Ft. Pool House, Creating An Exceptional Resort-Style Setting. The Garage Features A Car Lift And Accommodates Up To Five Vehicles, With Total Parking For Up To Thirteen Cars. A Rare And Distinctive Residence Created For Grand-Scale Living, Entertaining And Enduring Family Memories.

42 Wimpole Drive, Toronto

Listing courtesy of ROYAL LEPAGE REAL ESTATE SERVICES NANCY SAEDI.

$9,799,000

4 Beds ⋅ 7 Baths ⋅ W13584224 MLS® #

Welcome to 57 Baby Point Crescent, a breathtaking 1929 Tudor estate reimagined into a modern masterpiece, blending timeless character with contemporary luxury and cutting-edge technology. Set on an extraordinary 100' x 277' ravine lot, this exceptional home has undergone over $6 million in renovations in one of Toronto's most prestigious neighbourhoods.The restored exterior features a J.W. Fiske cast-iron fountain, heated cobblestone driveway, and parking for up to 10 vehicles. Inside, exceptional craftsmanship is showcased throughout, including a Scavolini chef's kitchen with premium Wolf and Gaggenau appliances, radiant-heated herringbone oak floors, and floor-to-ceiling European folding glass doors opening to a private ravine.Spa-inspired bathrooms feature heated marble floors, European wall-mounted toilets, concealed HVAC, motorized blinds, and recessed lighting. A premium audio system with 60+ Bowers & Wilkins speakers, powered by Bryston, Sonos, and NAD amplifiers, extends throughout the home and outdoor entertaining areas.The lower level is designed for entertainment and wellness with 10-foot ceilings, polished concrete floors, a full-size arcade, professionally designed gym, indoor sauna, and walkout to a year-round heated pool, hot tub, and all-season patio with infrared heaters.App-controlled smart home automation manages lighting, blinds, HVAC, security, Audio access, pool, spa, and sauna. Residents also enjoy exclusive access to the Baby Point Club with tennis courts, lawn bowling, and community events. A durable composite cedar roof with an expected lifespan of up to 60 years completes this truly one-of-a-kind luxury residence.

57 Baby Point Crescent S, Toronto

Listing courtesy of REMAX YOUR COMMUNITY REALTY.

$9,500,000

6 Beds ⋅ 8 Baths ⋅ C13158740 MLS® #

A rare offering in the heart of prestigious Teddington Park, this extraordinary custom residence sits on an impressive 71 x 180 ft landscaped lot surrounded by some of Toronto's most distinguished homes. Thoughtfully redesigned with exceptional craftsmanship and luxurious finishes throughout, this landmark property blends timeless elegance with sophisticated modern living. Featuring over three levels of meticulously designed living space, the home offers 5+1 bedrooms, 8 bathrooms, soaring ceilings, stunning hardwood & herringbone floors, designer marble and porcelain finishes, and a dramatic open riser glass staircase anchoring the grand foyer. The chef-inspired kitchen is a true showpiece with floor-to-ceiling windows, premium appliances, extensive custom cabinetry, servery and seamless flow into the family and entertaining spaces. Designed for both family living and upscale entertaining, the residence features multiple walk-outs, a home theatre, exercise room, lower-level guest/nanny suite, and beautifully appointed formal and informal living areas. The professionally landscaped grounds offer exceptional privacy, manicured gardens, and an elegant circular driveway.Ideally located steps to the Rosedale Golf Club, Yonge Street shops and restaurants, top-rated schools, parks, and transit, this exceptional home offers refined living in one of Toronto's most coveted neighbourhoods.

27 Teddington Park Avenue, Toronto

Listing courtesy of ROYAL LEPAGE SIGNATURE REALTY.

$9,499,000

5 Beds ⋅ 6 Baths ⋅ C13753586 MLS® #

A Custom Built Estate of Rare Distinction, Masterfully Crafted With an Uncompromising Commitment to Quality, Architectural Integrity, and Timeless Design. A Commanding Gated Presence Introduces the Residence, Clad in Distinguished Indiana Limestone and Crowned With a Handcrafted Copper Dome Roof-an Iconic Silhouette of Prestige and Permanence. The Grounds Are Nothing Short of Extraordinary, Showcasing Meticulously Curated Gardens and Masterful Landscape Design That Create a Breathtaking Arrival and a Private Botanical Sanctuary. Inside, Grandeur And Functionality Exist in Perfect Harmony. The Dramatic Entrance Hall Captivates Beneath a Soaring Double height Domed Ceiling, Anchored by a Sweeping Circular Staircase and Complemented By a Private Elevator Servicing All Levels. Principal Rooms Unfold With Effortless Flow, Framed By Expansive Windows That Capture Tranquil Garden Vistas From Every Vantage Point. Each Secondary Bedroom is Generously Proportioned, Complete With Its Own Walk-in Closet and Private Ensuite. Ideally Situated in the Heart of the Prestigious Bridle Path widely Regarded Among the World's Most Exclusive Neighbourhoods-moments to Sunnybrook Park, Premier Schools, Renowned Hospitals, Elite Golf Clubs, the Granite Club, and Convenient Highway Access.

18 Suncrest Drive, Toronto

Listing courtesy of THE AGENCY.

$9,488,888

6 Beds ⋅ 7 Baths ⋅ C13685530 MLS® #

A Rare Forest Hill Landmark - Rich in History, Character & Possibility Set on an exceptional 75 x 175 ft lot in prestigious Forest Hill, this distinctive pink stone residence, built in 1913, is a rare offering of architectural character, scale and privacy. Originally a private residence, it later served as Cantab College, a boys' school during the Depression, before being acquired by the current owners in 1985 and lovingly restored from the ground up.The home offers an elegant balance of period character and modern family living. A welcoming vestibule opens to a gracious central hall, leading to a library, formal dining room with fireplace and expansive living room with bay window and fireplace. The heart of the home is an integrated kitchen, eating and family living area with a dramatic two-way fireplace, opening directly to the large patio, landscaped gardens and private swimming pool.The upper levels provide generous bedroom accommodation, including a principal bedroom with fireplace and ensuite, additional ensuite bedrooms and a substantial third-floor bedroom/sitting room with three-piece ensuite and cedar closet.The lower level features approximately seven-foot ceilings and exceptional flexibility, with a gym, private movie theatre with fireplace, bathroom, rooms historically used for live-in help, wine cellar and extensive storage. The space can readily accommodate offices, hobbies, wellness or additional living areas.A detached two-car garage and pool cabana with washroom complete the property. Minutes from Upper Canada College and B.S.S., with Forest Hill's renowned schools, parks and amenities nearby.A truly special residence offering history, character, privacy, exceptional outdoor living and the rare potential of a 75 x 175 ft lot.

287 RUSSELL HILL Road, Toronto

Listing courtesy of RIGHT AT HOME REALTY.

$9,280,000

5 Beds ⋅ 8 Baths ⋅ W13487728 MLS® #

The North Drive Manor is a bold celebration of majestic design built by a master builder. This crown jewel in Humber Valley is beautifully positioned on the ravine with mature green vistas. A reflection of great success, it offers life in the lap of luxury.Blending visionary design, exquisite detail, and artistic touches, North Drive Manor exudes opulence reserved for a select few. Shielded by the ravine, the estate redefines privacy. A grand entrance leads to a splendid motor court ideal for gatherings or entertaining. The brick and limestone facade with slate roof enwraps sumptuous interiors introduced by a magnificent entry. The great room boasts a grand fireplace, while the formal dining and living rooms set the stage for elegant affairs.A chefs dream, the gourmet kitchen features professional appliances and a walk-in pantry overlooking the pool and ravine. Other highlights include a games room, grand library, walk-in wine cellar, and terrace.The upper-level principal suite offers a grand entrance, sitting room with fireplace, walk-in dressing room, and private spa ensuite. Four additional bedroom suites provide lavish accommodations for family and guests.The lower level presents endless recreation: a billiards room, home gym, bar, and home theatre. A three-car garage with height for lifts adds convenience.Designed by a renowned landscape architect, the grounds feature vast lawns, mature trees, and gardens. Enjoy alfresco dining poolside under the stars while hosting grand celebrations or intimate gatherings.Every element reveals extraordinary care and attention. North Drive Manor is unmatched a superlative estate designed for a modern-day dynasty, close to the country's finest schools, golf clubs, boutique shops, and restaurants.A world of magnificence awaits!

43 North Drive, Toronto

Listing courtesy of HAMMOND INTERNATIONAL PROPERTIES LIMITED.

$9,199,000

4 Beds ⋅ 5 Baths ⋅ C14081650 MLS® #

115 St. Leonard's Avenue Presents A Rare Opportunity To Create An Extraordinary Custom Residence In The Heart Of Lawrence Park. Architecturally Designed And To Be Built By ARKLAB Design Build, With Plans And Approvals Already In Place, This Is An Opportunity To Become Involved Before Construction Begins And Work Directly With The Architect/Builder As The Home Comes To Life. With Construction Yet To Begin, There Is Still Time To Personalize Select Finishes And Details, Allowing The Home To Feel Even More Uniquely Yours From The Moment You Move In. Envisioned With The Scale, Refinement And Presence Of A Showhome, The Residence Pairs Timeless Architecture With Rich Natural Materials, Sculptural Details, Extensive Custom Millwork And Beautifully Considered Lighting Throughout. Grand Principal Rooms, Dramatic Ceiling Treatments, Statement Stone, A Spectacular Chef's Kitchen And An Indulgent Primary Retreat Are Designed To Feel Both Impressive And Exceptionally Livable, While The Private Rear Grounds Are Conceived As A Resort-Like Extension Of The Home With A Pool And Beautifully Landscaped Entertaining Spaces. Set On One Of Lawrence Park's Tree-Lined Residential Streets, The Property Is Surrounded By The Ravines, Parks And Established Character That Have Defined The Neighbourhood For Generations, While Remaining Close To Yonge Street, Transit, Shops, Dining And Many Of Toronto's Most Respected Schools. This Is Not Simply A New Build, But An Opportunity To Create A Truly Exceptional Residence In One Of The City's Most Established Neighbourhoods.

115 St Leonard's Avenue, Toronto

Listing courtesy of HARVEY KALLES REAL ESTATE LTD..

$8,998,000

5 Beds ⋅ 7 Baths ⋅ C13224476 MLS® #

Some homes are built to a budget. This one was built without compromise - a rare residence of extraordinary quality and craftsmanship that would be nearly impossible to replicate today for the asking price. Set in prestigious Lytton Park, this custom-built three-storey estate offers approximately 6,500 sq. ft. of impeccably designed living space where luxury and meticulous attention to detail are evident throughout. Wrapped in custom-cut Indiana limestone and crowned with a premium Inspire roof, it is a true landmark residence. Inside, custom coffered ceilings, plaster mouldings, designer Restoration Hardware lighting, and marble finishes create rare sophistication. The chef-inspired kitchen is a showpiece: custom lacquer cabinetry, Italian marble slab counters and backsplash, premium appliances, an oversized centre island, and a butler's pantry. The family room centres on a dramatic floor-to-ceiling illuminated onyx fireplace surround. The third-floor suite offers exceptional flexibility, with a custom lacquer bar and illuminated onyx countertop. The primary suite is a private retreat with a spa-inspired ensuite and heated marble floors. The lower level rivals the finest private clubs - a gym, home theatre, wet bar, wine cellar, nanny's suite, sauna, and radiant heated floors throughout. Outside, the resort-inspired rear yard showcases a breathtaking stone pool and entertaining spaces worthy of a country club. Additional features include a heated driveway, automated lighting, multi-floor elevator access, and a garage with a two-car lift. This is more than a home; it is a statement of craftsmanship and architectural excellence - a one-of-a-kind offering in one of Toronto's most coveted neighbourhoods, setting a new benchmark for luxury living.

327 Cortleigh Boulevard, Toronto

Listing courtesy of HARVEY KALLES REAL ESTATE LTD..

$8,995,000

8 Beds ⋅ 7 Baths ⋅ C14098876 MLS® #

Re-Imagine This Amenity Rich Signature French Country Estate, Dramatic Facade With Exquisite Stone Accents, With A Spectacular Premium Corner Locale On Ravine With Panoramic City Views And The Rosedale Golf Club. Located Within On One Of The Most Sought After Enclaves Of The Exclusive Bridle Path-Sunnybrook-York Mills Neighborhood. A Tranquil Oasis Of Classic Luxury. This Estate Features A Main Floor Primary Retreat Complete With Spa-Like 5-Piece Ensuite And Walk-In His/Hers Dressing Room Plus Gym, A Separate In-Law Or Guest Suite Complete With Kitchen And Living Room, Bedroom & Ensuite, Five Additional Bedrooms Suites On Its Upper Level. Rich In Hardwood Floors, Elegant Custom Mouldings, Numerous Walk-Outs, And The Finest Luxury Appointments Throughout. The Main Floor Boasts A Gourmet Kitchen With Breakfast Area Plus Servery, Formal Dining Room and Living Room With Fireplace Featuring Custom Stone Surround, Library With Masterful Millwork, Sunken Great Room With 24' Vaulted Ceiling and Walkout To The Rear Garden With Towering Windows With Private Views To Its Lush Ravine. A Sprawling Lower Level Completes The Residence With Rec Room, Games Room, Craft Room, Gift Wrapping Room, Nanny Suite With Kitchenette, And Ample Space For Your Customization. The Exterior Features Are Rich In Resort-Like Amenities Such As An In-Ground Paradise Pool, Hot Tub, Stone Walkways, Cabana, Integrated Lighting, Irrigation, Private Sport Court, Cabana With Full Bathroom Plus Wet Bar, Multiple Lounge Areas, Majestic Lawns, All Surrounded By Lush Greenery And Mature Trees, And Wood Deck Overlooking The Ravine. The True Pinnacle Of Elegance, Privacy, And Luxury, All Near To Renowned Public And Private Schools, York Mills Shopping Centre, Trendy Eateries, Granite Club And Rosedale Golf Club.

17 Bayview Ridge, Toronto

Listing courtesy of RE/MAX REALTRON BARRY COHEN HOMES INC..

$8,995,000

5 Beds ⋅ 5 Baths ⋅ C13820026 MLS® #

Nestled on a 66 X 102 Ft Lot on Ardwold Gate, this exceptional custom-built residence offers sophisticated design,impeccable craftsmanship, and thoughtfully curated living spaces. A landscaped front entrance, concrete drivewaywith parking for six, and keyless entry set the tone for this remarkable family home.A marble floor foyer welcomes you into beautiful principal rooms, including a private home office with custom built-ins, formal living room, intimate dining area, and an impressive sunken family room with soaring ceilings, fireplace,and floor-to-ceiling sliding glass doors overlooking the backyard. The designer kitchen is a true showpiece,featuring an centre island, premium Wolf, Sub-Zero and Fisher & Paykel appliances, pantry, and seamless accessto the outdoor entertaining space. A temperature-controlled glass wine cellar, wet bar, integrated Sonos speakersystem, custom millwork, and wide-plank hardwood flooring elevate every level of the home.The second floor offers three spacious secondary bedrooms, a dedicated office, laundry room, and an extraordinaryprimary retreat complete with fireplace, private rooftop terrace, custom walk-in dressing room with centre island,and a luxurious heated 6-piece ensuite with steam shower and skylight.The finished lower level features a spacious recreation room, full bathroom, and abundant storage.Designed for effortless indoor-outdoor living, the professionally landscaped backyard boasts a covered outdoorkitchen with Lynx BBQ and bar fridge, expansive entertaining areas, swim spa, lush green space, and direct accessto Glen Edyth Drive.Located moments from Toronto's finest schools, parks, and amenities, this is an extraordinary opportunity to owna truly distinguished family residence.

75 Ardwold Gate, Toronto

Listing courtesy of HARVEY KALLES REAL ESTATE LTD..

$8,995,000

7 Beds ⋅ 5 Baths ⋅ C13782178 MLS® #

Situated in the heart of North Rosedale, Whitney Avenue is a picturesque street of established homes set beneath a leafy canopy. For more than a century, it has held sway as one of Toronto's most established addresses; minutes from the ravine and the shops of Yonge and Summerhill, and within reach of the city's best public and private schools. Number 20 is a centre-hall home in the classical style, taken back to its bones and reimagined by designer Connie Braemer in a contemporary renovation featured in House & Home. The result keeps the formality and proportion of the original architecture while opening the house up to create spaces perfectly-tailored for today's families. A striking foyer in concrete-look slab sets the palette that carries through the home: charcoal and warm rift-cut white oak, ebony-stained millwork, and black-framed glass doors that keep sight lines open while defining each room and setting the tone.The formal living and dining rooms at the front of the house have been reimagined through a modern lens while maintaining a sophisticated edge. Behind them, the wall between kitchen and family room has dissolved, creating an expansive open space for family living and entertaining, a striking kitchen anchored by a La Cornue range, and a rare servery kept within the expanded footprint. Oversized sliding doors open the family room onto the patio with outdoor living, swimming pool, and integrated hot tub. Upstairs, the primary suite has two walk-in closets and a marble-look porcelain ensuite, with a second bedroom and dedicated library on the same floor. The third floor holds three more bedrooms, and the lower level adds a recreation room, a wine cellar, and an additional bedroom. Secluded and private, yet minutes from the amenities those who call Rosedale home enjoy.

20 Whitney Avenue, Toronto

Listing courtesy of ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM.

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