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44 Cotswold Crescent, Toronto
$4,888,000
6 Beds ⋅ 5 Baths ⋅ C13731758 MLS® #
Perfectly situated on one of St.Andrew-Windfield's most coveted Streets-Welcome to 44 Cotswold Crescent-A Distinguished Custom Built Residence Offering Over 4000 Square Feet of Beautifully Appointed Living Space. Grand Principal Rooms, 3 Prestigious Fireplaces, A perfect blend of refined finishes and thought out floorplan. The Main Floor Features Distinctive Architectural Details-Greeted by a grand foyer with Columns framing the entrances to two principal rooms at both sides- An impressive library featuring solid wood built-in bookcases and on the other, a guest room with intricate detailed mouldings and grandeur wooden fireplace mantle. Step into the grand formal foyer with a soaring masterpiece staircase with a distinguished white turned balusters with detailed craftsmanship. Graciously sized- kitchen handcrafted and custom designed by the renowned Falcon Kitchen with a generous sized island perfect for entertaining and breakfast area surrounded by green lush backyard view and plenty of sunlight. Walk alongside the sun filled oak doors and oak framed windows of the backyard, you will be greeted to a wonderfully curated family room with oakwood ceiling beams and built-in shelves. The floorplan flows beautifully upstairs: Four well-proportioned bedrooms, including a spacious Primary bedroom with a formal ensuite retreat & A walk-in closet. Oversized recreation room, a private sauna and plenty of storage space in the basement level. A rare architectural masterpiece rarely available In The Heart Of St.Andrew-Windfield's, steps from Top-Ranked Public and Private Schools. Beautiful South East Exposure, Well-Landscaped Backyard Creates A Private Outdoor Retreat Perfect for Effortless Summer Entertaining. Lot is surrounded by mature trees offering private sanctuary in the heart of the city and backing onto the park for even more privacy. A gated two car garage allows for added security.

44 Cotswold Crescent, Toronto

Listing courtesy of KELLER WILLIAMS REFERRED URBAN REALTY.

40 Thelma Avenue, Toronto
$4,888,000
4 Beds ⋅ 6 Baths ⋅ C13713204 MLS® #
Welcome to 40 Thelma Avenue, a masterfully designed four-level home in the heart of Forest Hill Village. Just steps from the neighbourhood's beloved shops, cafes, and restaurants, and moments from prestigious private schools including Upper Canada College and The Bishop Strachan School, this residence offers an exceptional blend of luxury, location, and lifestyle. Designed by renowned architect Richard Wengle and completed in 2023, this custom-built home spans over 4,500 square feet of beautifully curated living space. Exquisite custom cabinetry and millwork elevate every room, while a fully integrated smart home system provides seamless control of lighting, audio, TVs, window coverings, climate, and security. Generous ceiling heights and floor-to-ceiling windows on every level flood the home with natural light, while built-in surround sound enhances the living experience throughout. Outside, a heated driveway and heated rear patio provide year-round comfort and convenience, complemented by discreet security bollards for added peace of mind. The stunning kitchen is designed for both everyday living and entertaining, complemented by a temperature-controlled wine cabinet ideal for collectors. The second floor features two spacious bedrooms, each with an ensuite, plus a versatile den or play area with its own ensuite that can easily be converted into a fourth bedroom. A dedicated laundry room adds convenience. Occupying the entire top floor, the primary suite is a luxurious private sanctuary featuring a spacious bedroom with walkout balcony, oversized glass-enclosed shower, separate soaking tub, double vanity, custom makeup station, private office, and dedicated wellness space. With timeless architecture, exceptional finishes, intelligent design, and an unparalleled location, 40 Thelma Avenue is a rare opportunity to own an extraordinary home in one of Toronto's most prestigious and walkable neighbourhoods.

40 Thelma Avenue, Toronto

Listing courtesy of HARVEY KALLES REAL ESTATE LTD..

38 Avenue Road Unit 700, Toronto
$4,880,000
3 Beds ⋅ 4 Baths ⋅ C13686632 MLS® # ⋅ The Prince Arthur BLDG.
Join the residents of The Prince Arthur, nestled between Yorkville and The Annex, and experience the luxury of privacy with an attentive Concierge, valet parking and the delivery of packages to your suite in one of Toronto's most sought after locations. Enjoy the space (approx. 3,115 sq ft) combining quality traditional finishing and built-ins with a renovated modern kitchen featuring exquisite high-end appliances. A thoughtful layout presents several separate private areas: primary/sitting room bedroom and second bedroom at one end, 3rd bedroom at the opposite end, a double door private library off the living room and separate formal dining room with a balcony. There are 3 bedrooms, 4 washrooms, library, 3 parking spaces, 2 lockers and 2 balconies for your family to enjoy. The south tower has a welcoming lobby entrance with tasteful art and decor. Generous ensuite laundry area with laundry sink. Wonderful amenities include the Annex and Yorkville Lounges, Fitness and Rejuvenation Center with sauna, theatre, library and car wash. Live in the innovative and cultural heart of Toronto.

38 Avenue Road Unit 700, Toronto

Listing courtesy of SUTTON GROUP OLD MILL REALTY INC..

11 Country Club Drive, Toronto
$4,850,000
4 Beds ⋅ 6 Baths ⋅ W13574284 MLS® #
Looking for Privacy? Hidden within the coveted Lincoln Wood Neighbourhood, Welcome to 11 Country Club Dr. This remarkable residence offers timeless architecture, refined elegance, and an impressive collection of luxury upgrades designed for sophisticated living & effortless entertaining. From the moment you arrive, the beautifully crafted exterior & award winning landscaping create a stunning first impression. Inside, every detail reflects quality and comfort, with thoughtfully designed living spaces, rich finishes, and exceptional craftsmanship throughout. The gourmet kitchen is a chef's dream, featuring premium Sub-Zero refrigeration, Wolf six-burner gas range, built-in microwave, pot filler, heated flooring, and reverse osmosis water filtration. The luxurious primary suite offers a private retreat with a stunning skylit ensuite, while heated floors in all second-floor bathrooms provide year-round comfort. Entertain with ease with a whole home multi zone sound system extending throughout the main floor, lower level, and backyard oasis. The recreation room features built-in speakers and a complete entertainment system ready for streaming. Step outside into your own private resort style retreat featuring a inground salt water pool & dramatic waterfall, gas fire pit, custom cabana with bathroom, outdoor tv, outdoor granite kitchen with sink, bar & refrigerator. The professionally landscaped grounds provide exceptional privacy with mature Japanese Maples, Birch, Beech, Cherry Blossoms, Cedars, Hydrangeas, and Boxwoods. Recent enhancements include artificial turf and a putting green installed in 2025. Located moments from the prestigious St. George's Golf and Country Club, this extraordinary residence presents a rare opportunity to enjoy luxury, privacy, and convenience in one of the area's most desirable neighbourhoods. 11 Country Club Drive is more than a home, it is an exceptional lifestyle.

11 Country Club Drive, Toronto

Listing courtesy of KELLER WILLIAMS REFERRED URBAN REALTY.

8 Canary Crescent, Toronto
$4,838,000
5 Beds ⋅ 7 Baths ⋅ C13823792 MLS® #
Tucked away on a quiet crescent in the heart of Bayview Village, this fine residence offers luxurious design, owner-built quality and convenience with a snow-melting driveway and four-stop elevator. Step inside and you will be greeted with a wide and welcoming foyer and main floor office with soaring 14' ceilings, wall paneling and built-in shelves. Living room with gas fireplace, herringbone wide plank engineered hardwood floors, tray ceiling and cove lighting showcases an utmost luxurious impression. Spacious dining room connects to the main kitchen through a convenient second kitchen with its own cooktop and sink. Main kitchen is spacious and thoughtfully finished with porcelain flooring, built-in Miele appliances and slab centre-island, countertops and backsplash. Sizable family room with coffered ceiling, gas fireplace and built-in shelves seamlessly connects to the breakfast area, overlooking through a beautiful picture window the serene backyard and swimming pool. Upstairs, four large bedrooms, Primary with walk-out balcony, 6-piece heated-floor ensuite adorned with high-end plumbing fixtures and large walk-in closet, all bedrooms with their own ensuites. Elevator with 3 stops connects all floors. Basement features fifth bedroom with its own ensuite bath, large recreation area with heated floors, wet bar, exercise room and walk-out to the backyard and pool. Garage entry thoughtfully appointed with an abundance of closet space. Experience the finest of Bayview Village living at a convenient yet tranquil location.

8 Canary Crescent, Toronto

Listing courtesy of ROYAL LEPAGE TERREQUITY CONFIDENCE REALTY.

63 Gordon Road, Toronto
$4,800,000
6 Beds ⋅ 7 Baths ⋅ C14030588 MLS® #
Stunningly Renovated '25 Luxe Residence Nestled On A Coveted Corner Lot In One Of St. Andrews Most Desirable Enclaves With A Rare 3 Door Garage. This Extraordinary Residence Offers Exceptional Design, Soaring Ceilings, And Modern Finishes Throughout. A Grand Foyer Welcomes You With A Sweeping Staircase Cascading In Natural Light From A Skylight Above. Designed For Both Elegance And Functionality. The Gourmet Kitchen Is A Chefs Dream, Complete With A Breakfast Area And Walkout To A Deck That Overlooks Beautifully Landscaped Rear Gardens. A Sophisticated Main Floor Library Showcases Custom Wall-To-Wall Built-Ins And Rich Paneling. The Luxurious Primary Suite Is A Private Retreat With A Lavish Dressing Room Offering Both Open And Closed Storage, A Decadent 6-Piece Ensuite, And A Secluded Deck With Serene Garden Views. Four Additional Bedrooms And Three Well-Appointed Bathrooms Complete The Upper Level. The Expansive Lower Level Is Designed For Relaxation And Versatility, Featuring A Nanny Suite, Recreation Room With Gas Fireplace, An Exercise Room, Cedar Sauna, And A Bright Walk-Up. Outdoor Living Is Enhanced By A Stone Patio And An Inground Pool With Waterfall, All Surrounded By Mature Landscaping For Ultimate Privacy. Just Steps To Renowned Schools, Shops And Eateries.

63 Gordon Road, Toronto

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

155 Gough Avenue, Toronto
$4,795,000
7 Beds ⋅ 6 Baths ⋅ E13855270 MLS® #
An impressive new residence in Playter Estates, 155 Gough Avenue pairs a refined design with superior craftsmanship, generous scale and remarkable versatility. Approx 4,800 sqft unfolds across three levels plus a lower-level suite, backed by Tarion warranties. A gracious foyer introduces elegant principal rooms with European oak flooring, custom millwork and curated lighting. The living room features a Napoleon linear gas fireplace with a dramatic book-matched slab surround, while the dining room is ideal for formal entertaining. The sophisticated chef's kitchen combines custom white oak cabinetry, quartz surfaces, a waterfall island with seating for four and premium Miele appliances, including a 36-inch dual-fuel range and integrated refrigerator/freezer. A butler's pantry, speed oven and stylish dry bar with temperature-controlled wine fridge complete the entertaining spaces. The family room opens through a double sliding-door walkout to the rear deck. The private primary retreat offers a fireplace, custom built-ins, two walk-in closets and a spa-inspired ensuite w/ heated floors, freestanding tub and frameless glass shower. Four additional bedrooms, beautifully finished bathrooms & dedicated laundry provide comfort and convenience. The fully finished lower level functions as a self-contained extended-family suite with living and dining areas, eat-in kitchen, two bedrooms, laundry and terrace access ideal for multi-generational living, guests or private accommodation. Outside, a Unilock driveway, walkway & patio, and concrete porch & stairs w/ snow-melt technology, two natural-gas BBQ connections and a 48-amp Level 2 EV charger extend the home's functionality. Ideally situated in coveted Playter Estates area, close to the Danforth's restaurants, cafes and shops, Pape subway & the desired Jackman school. A rare turnkey luxury residence offering impressive scale, refined finishes and outstanding flexibility in one of Toronto's most desirable east-end neighbourhoods.

155 Gough Avenue, Toronto

Listing courtesy of BOUTIQUE REAL ESTATE CORPORATION.

108 Heath Street W, Toronto
$4,795,000
5 Beds ⋅ 6 Baths ⋅ C13793092 MLS® #
Stunning New Build In The Heart Of Deer Park. This Gorgeous Newly Constructed Home, Designed And Built By Khales Corp., Showcases Executive Living Over Three Stories With Exceptional Attention To Detail, Beautiful Proportions And Stunning Finishes Throughout. Offering A Thoughtfully Designed Layout Ideal For Both Everyday Living And Entertaining, This Beauty Includes A Main Floor With Large Living And Dining Areas, An Open-Concept Gourmet Kitchen With Pantry, Eat-In Island And Breakfast Area, And A Huge Family Room With Flush Walkout To The Deck And Large Yard. The Primary Bedroom Is Situated Over The Sprawling Third Floor, Creating A Private Retreat Complete With Its Own Deck, Large Walk-In His-And-Hers Closets, And A Spacious Ensuite With An Additional Study And/Or Nursery. The Second Floor Has An Open-Concept Lounge With Additional Sizeable Bedrooms Plus A Laundry Room, Offering Comfort And Flexibility For Family Living. The Basement Offers Radiant Flooring Throughout, With A Large Recreation Room And Walkout To The Rear Yard, Providing Even More Exceptional Living And Entertaining Space. Easy Mobility Throughout The Home With A Built-In Garage And Elevator Access To All Levels. Steps To Yonge Street And St. Clair, With Easy Access To Public Transportation And Just Steps To Summerhill, Offering Outstanding Convenience In One Of Toronto's Most Desirable Neighbourhoods. This Masterpiece Is Not To Be Missed.

108 Heath Street W, Toronto

Listing courtesy of HARVEY KALLES REAL ESTATE LTD..

25 Strathgowan Crescent, Toronto
$4,795,000
6 Beds ⋅ 5 Baths ⋅ C13758824 MLS® #
This Grande Dame of Lawrence Park is an absolute treasure. Sitting on a 96 x 144 foot wide double lot set back from the street on a hill, this majestic home greets you with a rare combination of warmth and elegance. A centre hall plan seamlessly offers a formal living room to the left and sophisticated office to the right, before leading down the hall to the separate formal dining room with a stamped metal tile ceiling. The bright family kitchen overlooking the stunning yard is a delight with a large centre island and premium stainless steel appliances. The adjoining breakfast room with banquet seating overlooks an oversized family room, with built-in shelving, separate desk area and fireplace. French doors lead to a stunning outdoor haven with a covered outdoor deck, an inground pool and cabana under a canopy of trees. A chic powder room and side-door mudroom round out this traditional elegant main floor. Five generous-sized bedrooms, one with an ensuite, along with a three-piece bath and full-size laundry make up the substantial second floor, with room for everyone in the family. The third floor primary suite is a serene oasis with an oversized five-piece bath, two large walk-in closets, two balconies flanking each side of the room and floor, and an especially spacious living space, making it the perfect retreat. The lower level offers an oversized recreation/media room with a kitchen conveniently attached, a nearby sauna, a private wine cellar, utility room and plenty of storage. Built in 1913 and extensively redesigned in 1996, this distinguished home is a rare find in the city. Boasting a total of 6,000 square feet over four floors this classic Edwardian offers endless opportunities to convene as a family or entertain both indoors and out. Steps to ravine walks and situated in the catchment for top-rated Blythwood Public School, Lawrence Park CI, Blessed Sacrament and close to private schools such as Toronto French School, Crescent School and Havergal.

25 Strathgowan Crescent, Toronto

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

26 Danville Drive, Toronto
$4,790,000
6 Beds ⋅ 7 Baths ⋅ C13567586 MLS® #
This Stunning Luxury Home Offers a Meticulously Designed Multi-Level Layout, Where No Detail Has Been Overlooked. Situated on a Quiet Street near Top Schools, Parks, and Shopping, It Features a Chef's Dream Kitchen with a Butler's Pantry, Pot-Filler Faucet, 6-Gas Stove, Paneled Fridge, Wall Oven/Microwave, Dishwasher, and a Spectacular Skylit Ceiling. The Spacious Interiors Boast 10-Ft Main-Floor Ceilings, Heated Floors(Basement & All Ensuite Washrooms), a Combined Family/Playroom, Extensive Wood Trim, Exotic Marble Finishes, and Elegant Designer Lighting. Additional Luxuries Include a Hotel-Style Wet Bar, Built-in Bose Sound System, CVAC, 2 Furnaces, a Steam Humidifier, Gas Fireplace, Washer/Dryer, Stylish Light Feature Walls, and Designer Window Treatments Truly a Masterpiece of Modern Living.

26 Danville Drive, Toronto

Listing courtesy of AVION REALTY INC..

35 Longwood Drive S, Toronto
$4,788,800
6 Beds ⋅ 8 Baths ⋅ C13669680 MLS® #
A rare offering in one of Toronto's most prestigious neighbourhoods, this exceptional residence embodies timeless elegance, uncompromising attention to detail and effortless luxury. Thoughtfully designed for both grand entertaining and comfortable family living, every space has been meticulously crafted to the highest standard, showcasing soaring ceilings, exquisite millwork, designer lighting and expansive principal rooms filled with natural light. At the heart of the home is a spectacular chef's kitchen featuring premium built-in appliances, custom cabinetry, a walk-in pantry, and an oversized marble waterfall island, all beautifully complemented by an elegant tray ceiling with crown moulding that adds architectural sophistication to the space. Seamlessly connected to the family room and breakfast area, it creates the perfect setting for everyday living and effortless entertaining while overlooking the beautifully landscaped backyard. Throughout the home, exceptional craftsmanship is paired with thoughtfully integrated modern conveniences, including automatic blinds and a heated driveway, ensuring comfort and convenience in every season. Offering 5 spacious bedrooms plus an additional lower-level bedroom, each with its own private ensuite, along with 2 elegant powder rooms, the home is thoughtfully designed to provide exceptional comfort and privacy for both family and guests. The generously proportioned primary suite serves as a luxurious private retreat, while the beautifully finished lower level offers exceptional additional living and entertaining space, perfect for hosting guests, a home theatre, gym or recreation area. Every detail has been carefully considered to create a home that is as functional as it is beautiful-an exceptional opportunity to experience luxury living in one of Toronto's most sought-after neighbourhoods.

35 Longwood Drive S, Toronto

Listing courtesy of HOMELIFE/VISION REALTY INC..

27 Berkinshaw Crescent, Toronto
$4,788,000
5 Beds ⋅ 6 Baths ⋅ C13835630 MLS® #
Thoughtfully envisioned and executed by renowned Arklab Design Build, this custom residence is a study in modern architecture balanced with the warmth and practicality of a true family home. Featured on Amazon's Luxe Listings Toronto, the home is flooded with natural light and occupies a generous lot on a quiet crescent. Beyond the solid mahogany entry door, a dramatic double-height dining room, sculptural red-oak staircase and glass railings make an immediate impression without feeling overstated. The main living spaces unfold naturally around the home's central gathering points. The kitchen is designed for serious cooking and entertaining, with two substantial islands and Wolf and Thermador appliances. The adjoining family room centres on a three-sided gas fireplace, custom bar and wine display, while an architectural ethanol fireplace gives the living room its own distinctive character. Upstairs, all four bedrooms feature private ensuites, giving every family member a sense of their own space. The primary suite is particularly considered, with his-and-hers closets, a custom entertainment unit and a heated ensuite featuring a skylit shower that draws in natural light. The lower level is equally impressive, with soaring ceilings, polished concrete, heated floors, two additional bedrooms, awalkout and wet bar. Technology is seamlessly integrated throughout: smart-home controls, built-in speakers, smart PDLC window film, security cameras and battery-operated blinds complement the design. Outside, a heated front porch, walkway and driveway add year-round comfort. A two-car garage and driveway parking for four additional vehicles ensure the practical details are as carefully resolved as the architectural ones. Dramatic yet comfortable, highly designed yet genuinely livable, and sophisticated without sacrificing the ease of family life, this is a rare combination of architectural pedigree, generous scale and thoughtful execution.

27 Berkinshaw Crescent, Toronto

Listing courtesy of KELLER WILLIAMS REFERRED URBAN REALTY.

67 Lynwood Avenue, Toronto
$4,750,000
5 Beds ⋅ 5 Baths ⋅ C13794624 MLS® #
Imagine walking into a home that truly has it all: a gorgeous, NEWLY renovated detached home! Pool! Elevator! Private drive leading to an integrated 2-car grg! Incredible family & entertaining space! Triple A+ school district! All on one of South Hill's most coveted streets. If you've been waiting for the house that checks every box - run, don't walk or you'll miss this unbelievable opportunity! Design savvy thru/out & move-in ready, this south-facing grand home delivers from the moment you walk in. A stunning entrance w/heated marble floors opens to a fabulous combined living/dining rm w/beautiful proportions, a gas f/pl & generous space to entertain. At the rear, a massive kitchen/family rm is the heart of the home w/ a wood-burning fireplace, breakfast area, & wall of glass overlooking the spectacular south-facing garden providing incredible natural light throughout the home. Step outside to a completely pvt, tree-lined oasis w/an oversized pool, hot tub, & multiple areas to lounge, dine, & entertain. The 2nd flr features a serene primary retreat overlooking the garden w/ large ensuite & amazing His A.N.D. Her walk-in closets, plus the family rm/den everyone wants, an additional bedroom, & a 2nd bath. Upstairs, two more huge bedrooms feature cathedral ceilings, a large bathroom, & a sun-filled deck w/city views. The staircase is an architectural feat w/streaming sunlight cascading in from the massive skylight. The lower lvl is just as impressive: gym, rec room, fantastic storage, & w/o to the backyard. The elevator servicing all 4 lvls is a rare & highly desired feature. Walk in from the integrated 2-car garage to a fabulous mudrm,private drive & parking for 4 & this house is almost impossible to beat. And then there's the LOCATION! Walk to UCC, BSS, The York School & Brown Public School, + ravines, parks, shops & restaurants. The space. The renovation. The pool. The garage. The elevator. The schools. The location. It's all here. See it before someone else does!

67 Lynwood Avenue, Toronto

Listing courtesy of ROYAL LEPAGE REAL ESTATE SERVICES OXLEY REAL ESTATE.

65 Bellwoods Avenue, Toronto
$4,749,999
5 Beds ⋅ 6 Baths ⋅ C13478726 MLS® #
Rare opportunity to acquire an iconic Trinity Bellwoods landmark offering approximately 11,634 sq. ft. across two levels. Originally constructed over a century ago, this extraordinary post-and-beam building showcases exposed triple-brick walls, heavy timber construction, soaring ceilings, expansive windows, and exceptional natural light throughout. Rich in history and character, the property was once home to the first Coca-Cola bottling operation outside the United States, established in 1906, and retains architectural features rarely found in Toronto today. Currently configured with residential and office components, the property presents a remarkable opportunity for a spectacular custom residence, live/work environment, creative studio, or other permitted uses, subject to purchaser due diligence and approvals. Situated moments from Trinity Bellwoods Park and the vibrant shops, cafes, restaurants, and culture of Queen West and Ossington, the property offers an unparalleled combination of scale, character, and location. Residential zoning with existing legal non-confirming office use provides exceptional flexibility for end-users, investors, architects, designers, and creative entrepreneurs seeking a truly irreplaceable asset in one of Toronto's most coveted neighbourhoods. A rare opportunity to restore, reimagine, and create a one-of-a-kind property where history, architecture, and future potential converge. Property being sold under Power of Sale in "as-is, where-is" condition.

65 Bellwoods Avenue, Toronto

Listing courtesy of THE BEHAR GROUP REALTY INC..

54 Plymbridge Road, Toronto
$4,688,000
5 Beds ⋅ 4 Baths ⋅ C14086116 MLS® #
A Rare Opportunity to Enjoy an Elegant Residence or Create a Bespoke Luxury Estate in Prestigious Hogg's Hollow! Nestled within one of Toronto's most coveted luxury enclaves, this exceptional property occupies a magnificent approximately114.48 x 328.39 ft(Irregular) estate-sized lot, offering extraordinary depth, privacy, and remarkable future potential. **Surrounded by mature trees, lush greenery, and a picturesque ravine setting, the property offers breathtaking natural surroundings, exceptional privacy, and a rare sense of tranquility in the heart of the city.** This distinguished property presents an exceptional setting for refined family living or the creation of a magnificent custom-built estate. The existing 4+1 bedroom, 4-bathroom residence offers generous living spaces and thoughtful updates, including an elegant stucco and stone exterior, interlock driveway, and renovated powder room. The expansive, fully fenced backyard features an in-ground swimming pool and a serene, resort-inspired retreat, ideal for family enjoyment and sophisticated outdoor entertaining. 200-Amp Electrical Service. Complete with parking for six vehicles, the property offers exceptional versatility for immediate enjoyment, future enhancements, or redevelopment. Ideally located near renowned public and private schools, picturesque parks, upscale amenities, transit, and major highways, this prestigious address seamlessly blends natural tranquility with urban convenience. An Extraordinary Opportunity to Embrace the Hogg's Hollow Lifestyle Today or Create a Landmark Estate for Generations to Come!

54 Plymbridge Road, Toronto

Listing courtesy of SOTHEBY'S INTERNATIONAL REALTY CANADA.

18 Chipstead Road, Toronto
$4,688,000
5 Beds ⋅ 5 Baths ⋅ C13440660 MLS® #
Welcome to 18 Chipstead Road, an entertainer's dream home, conveniently located in the heart of Denlow near Bayview and 401 with great schools and lots of local shopping nearby. This fully renovated 4200 + square foot home is one of the nicest homes in the area. Interior designers Jeffrey Douglas and Chantal Philippe contributed to the designs and furnishing choices. Landscape architect Wendy Berger and her team contributed to the landscape architecture. From the moment you walk in the front door, you know this home is calming and special. Super spacious, yet oh so warm and cozy. New custom stairs and railings. Massive 2-story upper hallway with 4 oversized skylights. The brand new open concept custom kitchen/family room has tons of natural light and a new linear Regency gas fireplace. The almost 45-foot-long lounge/living/dining room combination is great for entertaining. The powder room is stunning. The pantry/mud room is off the main hall and has plenty of cupboards and counter space. It also has a separate full-size fridge, wine fridge and dishwasher. The pantry connects to the garage which has polyaspartic floors. The primary suite is an open concept retreat with a coffered ceiling and plenty of natural light. The Regency 3-sided gas fireplace enhances the bedroom and the primary lounge area. The primary bath has a 2-person shower and a separate soaking tub, overlooking the primary upper deck that overlooks the pool. The primary custom backlit closet is expansive with 2 skylights. All other bedrooms are king-size rooms with 2 additional en-suites and custom finishes. The basement has an open concept media area with a gas fireplace and room for a card table, pool table, and multiple workout areas. The backyard oasis has dining under the primary upper deck as well as a lounge area off the pool. Recent renovations in excess of $1,000,000. Main floor ceiling height 8 feet, second floor ceiling height 8.5 feet, 2-story atrium.

18 Chipstead Road, Toronto

Listing courtesy of THE OTHER GUYS REALTY CORP..

108 Yorkminster Road, Toronto
$4,650,000
6 Beds ⋅ 6 Baths ⋅ C14096276 MLS® #
Stunning Custom-Built Family Home In The Prestigious St. Andrew-Windfields neiboorhood. Offering over 7,200 Sq. Ft. Of Luxury Living Space. Sun Filled Living room oversees the front yard garden, connected to the spacious Dining room surrounded professional millwork and coffered ceiling. Featured Family room equipped with a fireplace and B/I Shelves, and overlooks the backyard Oasis. Chef inspired kitchen includes a large centre island, beautiful granite countertops and backsplash, top of the line appliances, Custom Kitchen Cabinetry, and a Built-in Pantry. The private office with Mahogany panelled wood walls. Classic Wrought iron Staircase with a skylight leads to the upper floor, which features a luxurious primary bedroom with a fireplace, sitting area, walk in dressing room and 6pc ensuite with heated floors. Four other bedrooms all with access to ensuites. The lower level Boasts an entertainment and relaxation paradise, Large Rec Room with Wet Bar, Exercise Rm, Red Wood Rack Wine Cellar, Home Cinema and Cedar Closet. Also an extra bedroom with 3pc Bath. Walk up to the backyard. Radiant Heated Floors on Main Floor & Basement. Minutes To Golf, Highway and Public Transit. Top tier Private & Public Schools, branding Shopping & Dining. An exceptional family home offering timeless craftsmanship, refined living, and an enviable address in one of Toronto's most prestigious neighbourhoods.

108 Yorkminster Road, Toronto

Listing courtesy of ROYAL LEPAGE PEACELAND REALTY.

94 Roxborough Drive, Toronto
$4,650,000
3 Beds ⋅ 3 Baths ⋅ C14027922 MLS® #
A rare blend of sophistication, privacy & serenity at 94 Roxborough Drive, an extraordinary North Rosedale residence. Nestled beneath a lush canopy of mature trees with no immediate houses on either side, this architectural gem offers a peaceful retreat just minutes from downtown. Originally built in the 1950s by Howard Chapman, son of renowned Canadian architect Alfred Chapman, the home was extensively renovated in 2021, marrying its architectural heritage with contemporary design & exceptional craftsmanship. Spanning approximately 3,000 sq. ft., light-filled interiors feature refined entertaining spaces, 3 beautifully appointed full bathrooms & flexible bedroom configurations. At the heart of the home, a spectacular custom kitchen boasts a 13' island, 8' picture window overlooking the forest-like gardens, Canadian granite counters, bespoke cabinetry, Wolf gas cooktop, steam oven, warming drawer & Miele dishwasher. The adjoining great room evokes the warmth of a luxurious modern chalet, with soaring ceilings, loft, gas fireplace & white oak flooring. Architectural details include a marble foyer, bevelled-glass entry, designer lighting & sculptural staircase. The private upper-level primary suite offers a luxurious ensuite, separate shower room & elegant dressing room. A versatile office or additional bedroom enjoys tranquil treetop views. A secluded side terrace provides an intimate setting for outdoor dining & entertaining. Automatic blinds, 1.5-car garage & private double driveway add everyday convenience. Featured in an international architecture publication & luxury home series, this remarkable property offers the presence of a larger estate without its maintenance demands. Steps to Summerhill Market & ravine trails, with Yonge St., transit, shops & fine dining nearby. A rare opportunity to own an exceptional North Rosedale sanctuary where architecture, nature & urban living exist in perfect harmony.

94 Roxborough Drive, Toronto

Listing courtesy of CHESTNUT PARK REAL ESTATE LIMITED.

41 Nanton Avenue, Toronto
$4,650,000
4 Beds ⋅ 3 Baths ⋅ C13135368 MLS® #
Visit REALTOR website for additional information. Exquisite Georgian Revival Residence on Coveted Nanton Avenue, Rosedale Seldom does an opportunity of this magnitude present itself.Situated on one of Rosedale's most prestigiousstreets,this grand three-storey Georgian Revival residence occupies a rare 50x150-foot lot,offering exceptional privacy and expansive outdoor living.Designed by renowned architectBeaumont Jarvis as his own personal residence, the home is rich in history,elegance,andarchitecturalsignificance. Its timeless beauty has also attracted Hollywood attention,havingbeen featured in acclaimed television productions including Suits and 12Monkeys.Thedistinctive Dutch Gambrel roof and stately façade create an unforgettable first impression.Inside,the home has been meticulously restored to preserve its original charm whileincorporating modern luxury.Extraordinary period details include soaring 4x16-foot beams,leaded and stained-glass windows,intricate mouldings,and grand principal rooms designed forelegant entertaining and comfortable family living.A chef-inspired kitchen features aFrench-imported Lacanche range and premium Gaggenau refrigeration.Two staircases connect the thoughtfully designed three levels, balancing sophistication withpracticality. The rear mudroom opens to breathtaking mature gardens and an oversized backyardoasis with private garage,perfect for entertaining, alfresco dining,or even a private skatingrink beneath the stars in winter.Offering four spacious bedrooms and three beautifully appointed bathrooms,the home provides abundant natural light and refined comfort throughout.One of Toronto's original poured concrete homes,it boasts remarkable durability and structuralintegrity rarely found today.Located steps from the subway, this exceptional residence combinesserene luxury with effortless downtown Toronto access.Surrounded by top-tier schools and acelebrated family-friendly community,this is a rare opportunity to own a landmark property

41 Nanton Avenue, Toronto

Listing courtesy of PG DIRECT REALTY LTD..

57 Wimpole Drive, Toronto
$4,599,888
4 Beds ⋅ 4 Baths ⋅ C13536678 MLS® #
***A Rare Offering In The Prestigious Bayview And York Mills Enclave***This Beautifully Renovated Ranch-Style Bungalow Sits On An Exceptional South Facing 110x132 Ft Estate Lot Surrounded By Mature Trees And Timeless Elegance. The Home Has Been Meticulously Updated And Renovated Over The Years, Blending Refined Finishes With The Warmth And Ease Of Single-Level Living. Its Three-Bedroom Layout Is Bright, Sophisticated, And Designed For Comfort, Creating A Welcoming Atmosphere From The Moment You Arrive. Live In It Today, Make It Your Dream For The Future. The Property's Expansive Grounds Are Truly Extraordinary. A Serene Pond, Lush Perennial Gardens, And Towering Trees Form A Private Natural Sanctuary That Feels Worlds Away From The City, Offering An Unmatched Sense Of Calm And Retreat. The Backyard's Scale And Beauty Provide Endless Opportunities For Outdoor Living, Entertaining, And Quiet Relaxation. Whether Enjoyed As-Is Or Envisioned As The Foundation For A Future Custom Residence, The Lot Delivers Exceptional Value In One Of Toronto's Most Coveted Neighbourhoods. The Curb Appeal With Stunning Grounds Enhance The Estate-Like Presence Of The Home. Inside, Thoughtful Renovations Have Created A Move-In-Ready Environment With Stylish Updates, Generous Principal Rooms, And A Seamless Connection To The Outdoors. This Is A Rare Chance To Secure A Beautifully Maintained Bungalow On A Premium Oversized Lot In An Area Known For Luxury Homes, Top-Tier Schools, And Unparalleled Convenience. 57 Wimpole Offers A Stunning Blend Of Tranquility, Prestige, And Long-Term Potential, An Exceptional Opportunity For The Discerning Buyer.

57 Wimpole Drive, Toronto

Listing courtesy of ROYAL LEPAGE SIGNATURE REALTY.

101 Banbury Road, Toronto
$4,599,000
5 Beds ⋅ 4 Baths ⋅ C14129722 MLS® #
Architecture That Moves You. A Home That Stays With You.An architectural masterpiece where extraordinary design meets exceptional living.Defined by dramatic proportions, natural light, and timeless sophistication, this remarkable residence offers over 6,000 sq. ft. of living space across three levels, including approximately 4,000 sq. ft. above grade.A breathtaking 20-foot foyer, artistic skylights, soaring ceilings, and floor-to-ceiling windows create an unforgettable first impression. Warm white oak flooring and refined finishes bring elegance and character to every space.At the heart of the home, a spectacular designer kitchen showcases natural marble countertops, a hand-carved sculptural marble island, Sub-Zero refrigeration, and integrated Miele appliances.The luxurious primary retreat features a spa-inspired ensuite with heated floors and a custom Oceania bathtub, while a rooftop deck, versatile living spaces, and two fireplaces elevate everyday comfort.Outdoors, a beautifully landscaped backyard with an in-ground swimming pool and entertaining terrace offers a private oasis. An impressive 111-foot frontage, extensive recent upgrades, and integrated smart-home features complete this exceptional property.Bold in architecture. Refined in every detail. Unforgettable by design.More than a home, it's an experience.

101 Banbury Road, Toronto

Listing courtesy of THE AGENCY.

94 Munro Boulevard, Toronto
$4,599,000
6 Beds ⋅ 6 Baths ⋅ C13835204 MLS® #
Welcome to an exceptional custom residence in prestigious St. Andrews, where refined architecture, timeless finishes and sophisticated family living come together on a beautifully landscaped 50 x 136 ft lot. Meticulously maintained, the home offers striking curb appeal with stone and brick construction, copper accents and a professionally landscaped front rock garden. Inside, elegant details include oak hardwood, vaulted and coffered ceilings, skylights throughout, wainscotting, crown moulding, cove lighting in living and dining, beautiful designer chandeliers and 10-ft ceilings on both the main and second floors. Featuring 4 bedrooms, each with an ensuite bathroom and heated floors, including a spacious primary retreat with fireplace, sitting area, walk-in closet and spa-like 5-piece ensuite with steam shower. A skylight adds incredible light to primary ensuite. Two additional lower-level rooms are currently used as a gym and nanny suite. The main level offers formal living and dining rooms, a richly finished mahogany office, family room with fireplace and walkout to the backyard. Stunning chef's kitchen with Sub-Zero refrigerator, Dacor 6-burner gas range, double ovens, centre island and butler's pantry. The lower level is designed for entertaining with a large rec room, built-in maple bar w fridge, home theatre with gas fireplace, games area, heated floors and walkout to the backyard. Storage room roughed in for another bathroom or 2nd laundry room. 2 high efficiency Lennox furnaces and AC units. A double-car garage w EV charger and private drive provide parking for 6 cars. Over 5200 total square feet of elegant living space, it's truly an exceptional custom home in one of Toronto's most coveted neighbourhoods.

94 Munro Boulevard, Toronto

Listing courtesy of PSR.

239 Borden Street, Toronto
$4,599,000
4 Beds ⋅ 5 Baths ⋅ C13792922 MLS® #
Located just south of Bloor in the heart of the Annex, this exceptional residence is within walking distance of some of Toronto's best restaurants, shops, cafés and neighbourhood amenities. Completely rebuilt and completed in July 2023, the home retains only its original facade, with every other element thoughtfully reimagined to deliver over 3,400 sq. ft. of refined living space across four levels. The second floor offers 3 spacious bedrooms, including a stunning principal retreat with a luxurious 5-piece ensuite, while the fully self-contained lower level provides a 4th bedroom or ideal in-law suite with its own kitchen, laundry and private walkout. Five beautifully appointed washrooms feature elevated materials and meticulous attention to detail. Designed by Lyndsay Jacobs Interiors and featured in House & Home and Timeless Living, the interiors showcase custom millwork, restored 1878 stained glass, white oak herringbone floors, and hand-selected marble and limestone imported from Greece. A dramatic3-storey staircase illuminated by skylights fills the home with natural light. The showpiece kitchen features custom cabinetry, a 17-ft floating Nero Borghini marble shelf, Thermador appliances and a 10-ft bifold door creating seamless indoor-outdoor living. The landscaped backyard offers an incredible opportunity for a 2-storey laneway house or garage with accommodations, adding tremendous future flexibility and potential. A rooftop terrace with saltwater hot tub and gas hookup offers treetop and CN Tower views. The lower level also features a custom media room with Bowers & Wilkins surround sound, a 400-bottleclimate-controlled wine cellar, dog wash station and extensive built-in storage.

239 Borden Street, Toronto

Listing courtesy of HARVEY KALLES REAL ESTATE LTD..

33 Tarlton Road, Toronto
$4,595,000
5 Beds ⋅ 5 Baths ⋅ C13790816 MLS® #
A distinguished collaboration of design, craftsmanship and modern elegance, 33 Tarlton Rd is an exceptional residence originally built by renowned Shram Homes and architecturally designed by celebrated Richard Wengle. Set on an impressive 35 x 124 ft lot, this sophisticated 4-bedroom, 5-bathroom home offers exceptional indoor-outdoor living, refined finishes and effortless entertaining. Rich hardwood floors complement a curated selection of sophisticated finishes, while the spectacular custom kitchen features top-of-the-line appliances, bespoke cabinetry and an expansive centre island. The elegant living room features a striking fireplace, while the family room, with custom built-ins and a second fireplace, opens seamlessly to the beautifully landscaped rear garden. A Lutron lighting system and integrated surround sound throughout the home and outdoor entertainment space further elevate the experience. The private rear garden features a tranquil water feature, covered entertainment area and expansive BBQ deck, creating an exceptional setting for entertaining. The luxurious primary suite includes a spa-like ensuite with heated floors, complemented by three additional generously sized bedrooms. A bright finished lower level with heated floors, recreation room and bedroom currently serves as an artist's studio and offers exceptional versatility. A two-car garage and heated driveway provide year-round convenience. Ideally located near exceptional schools, parks, shopping, dining and transit, 33 Tarlton Rd represents a rare convergence of architectural pedigree, contemporary luxury and sophisticated family living.

33 Tarlton Road, Toronto

Listing courtesy of HARVEY KALLES REAL ESTATE LTD..

29 Oaklands Avenue, Toronto
$4,595,000
4 Beds ⋅ 5 Baths ⋅ C13715072 MLS® # ⋅ The Charbonnel BLDG.
The Charbonnel is an architecturally distinguished boutique enclave of just 18 luxury townhomes in prestigious Summerhill. Like a freehold property with low monthly maintenance fees (covering manicured front gardening), this exceptional Richard Wengle-designed residence offers nearly 3,500 sq ft of sleek interior space, complemented by approximately 1,000 sq ft of private outdoor terraces & balconies, all connected by A PRIVATE ELEVATOR extending from the oversized two-car garage to the rooftop terrace. Designed for effortless indoor-outdoor living, this dynamic home showcases a privacy-screened main-level terrace with firepit adjoining the captivating family / great room, a spectacular rooftop retreat featuring a stone-clad fireplace, & multiple balconies all with transparent glass railings to maximize the uninterrupted panoramas, from the glittering downtown skyline to the ever-green, park-like vistas overlooking the De La Salle playing fields. Customized with an outstanding Brian Gluckstein finish package, the impeccable interiors combine timeless sophistication with contemporary design. Elegant European oak floors, exquisite marble & stone surfaces, dramatic, black-framed walls of glass, & a striking floating staircase crowned by an expansive skylight create an atmosphere of light & understated luxury. Numerous owner upgrades enhance both form & function, including a generous kitchen island, premium Miele appliances, & extensive custom built-ins. Heated floors throughout the kitchen, family rm, current dining rm, primary suite, & 1st floor ensure year-round comfort, while the highly versatile floor plan offers remarkable flexibility, including an ideal office or den near the entrance. All four bedrooms feature ensuite baths & generous walk-in closets. The serene primary retreat is particularly impressive, offering custom cabinetry & a luxurious six-piece spa-inspired ensuite illuminated by its own window.

29 Oaklands Avenue, Toronto

Listing courtesy of CHESTNUT PARK REAL ESTATE LIMITED.

2 Addison Crescent, Toronto
$4,558,000
5 Beds ⋅ 6 Baths ⋅ C13782388 MLS® #
A rare offering on coveted Addison Crescent, where sophisticated design, exceptional privacy and resort inspired outdoor living come together on an expansive, serene lot. Completely renovated to the studs, the home pairs refined finishes with exceptional craftsmanship and an effortless, light-filled flow. The custom chef's kitchen features porcelain surfaces, an oversized island and integrated Fisher & Paykel appliances, including a 48" gas range, built-in coffee system and wine fridge. Open-concept living and dining are framed by expansive windows overlooking the grounds, with a gas fireplace and integrated speakers. Generous principal rooms include a beautifully appointed primary retreat with spa inspired ensuite and walk-in closet, complemented by a skylit sitting room, private office with custom millwork and upper level laundry.The underpinned lower level offers 9' ceilings, hydronic in-floor heating, wet bar, lower level laundry, 5th bedroom, 3 piece bath and sauna. Outside, an in-ground pool and covered outdoor kitchen create an exceptional setting for summer entertaining. A built-in double garage, gated private drive and EV rough-in complete the property. Extensively upgraded with new HVAC, plumbing, electrical, high efficiency furnace and A/C, pool mechanicals, windows, metal roof, custom motorized front entry gate and garage doors. An exceptional offering where considered design, privacy and quality converge.

2 Addison Crescent, Toronto

Listing courtesy of SAGE REAL ESTATE LIMITED.

38 Fifeshire Road, Toronto
$4,549,999
5 Beds ⋅ 5 Baths ⋅ C13784786 MLS® #
A rare ravine lot, nearly half an acre in size! Seize the opportunity to build your dream home on one of Toronto's most prestigious streets, in the coveted Bayview and York Mills enclave. 38 Fifeshire Road offers a canvas of serenity and prestige - framed by mature trees and lush natural surroundings - ideal for visionary architects and discerning homeowners. The existing residence offers nearly 5,000 square feet of living space, but the true allure lies in the land's potential: imagine a custom estate with sweeping terraces, an infinity pool, or private gardens, tailored to your vision. Just moments from Bayview Village, top schools, fine dining, and easy access to major highways. This is more than a home - it's a legacy in the making on one of Toronto's most iconic streets.

38 Fifeshire Road, Toronto

Listing courtesy of HARVEY KALLES REAL ESTATE LTD..

23 Vernham Court, Toronto
$4,500,000
4 Beds ⋅ 7 Baths ⋅ C14132104 MLS® #
Set On An Impressive 157-Ft-Wide Lot At Courts End, This Sprawling, Stunning Updated Bungalow Offers The Space And Functionality Of A Two-Storey Home With The Convenience Of Main-Level Living. Thoughtfully Designed With An Emphasis On Scale, Natural Light, And Seamless Indoor-Outdoor Flow, The Residence Features Soaring 14-Ft Vaulted Ceilings, Skylights, And Dramatic Walls Of Windows Overlooking The Private Rear Gardens And Swimming Pool. Expansive Principal Rooms And An Open-Concept Layout Provide An Ideal Setting For Both Entertaining And Everyday Living, While The Beautifully Appointed Bellini Eat-In Kitchen Serves As The Heart Of The Home. Fine Craftsmanship And Carefully Considered Details Are Evident Throughout. An Elevator Connects To The Generously Sized Lower Level, Complete With Two Additional Bedrooms, A Large Recreation Room, Wet Bar, And Dedicated Office Area, Providing Versatile Space For Family, Guests, Or Extended Living. Outdoors, Mature Landscaping Creates A Private, Tranquil Setting Featuring A Swimming Pool And Spacious Deck, Perfect For Relaxing Or Entertaining. Complete With A Four-Car Garage, Heated Driveway And Access To The Renowned Harrison International Baccalaureate Program, This Distinctive Property Offers A Rare Combination Of Space, Privacy, And The Ease Of Bungalow Living.

23 Vernham Court, Toronto

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

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