21 Fifeshire Road

FOR SALE
$6,995,000
21 Fifeshire Road, Toronto
21 Fifeshire Road
21 Fifeshire Road
21 Fifeshire Road
21 Fifeshire Road
21 Fifeshire Road
21 Fifeshire Road
21 Fifeshire Road
21 Fifeshire Road
21 Fifeshire Road
21 Fifeshire Road
21 Fifeshire Road
21 Fifeshire Road
21 Fifeshire Road
21 Fifeshire Road
21 Fifeshire Road
21 Fifeshire Road
21 Fifeshire Road
21 Fifeshire Road
21 Fifeshire Road
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5 + 1
BEDROOMS
8
BATHROOMS
1
KITCHENS
12 + 3
ROOMS
C13797004
MLSID
Contact Us
Property Description
Bespoke Residence Set On A Stunning 121' Wide Manicured Lot Which Stands Among The Finest In Prestigious Estates On The Much Sought After St. Andrew-Windfields Neighborhood. Encompassing Approximately 8,300 Square Feet Of Curated Living Space With Ideal Entertainment Flow, The Residence Is Defined By Imported Marble, Rich Hardwood, Tailored Lighting, And Refined Designer Detailing Throughout. Beyond A Tree-Lined Circular Drive, The Stately 6+1 Bedroom, 9 Bathroom Home Reveals A Grand Foyer Of Striking Elegance, Where A Soaring Cathedral Ceiling With Skylight Bathes The Interiors In Natural Light, Accentuating A Sweeping Natural Stone Staircase With Custom Brass And Wrought Iron Railings. Gracious Formal Living And Dining Rooms, Alongside A Distinguished Library Adorned In Brazilian Redwood, And A Custom Chef's Kitchen, Anchor The Main Level With Timeless Sophistication. A Charming Breakfast Area And Expansive Family Room Seamlessly Extend To The Rear Garden Oasis, Creating An Effortless Setting For Both Intimate Gatherings And Entertaining. The Primary Retreat Is A Sanctuary Unto Itself, Featuring A Tranquil Sitting Area With A Custom Fireplace, His And Hers Walk-In Closets, And Accompanying His-And-Hers Ensuites. Five Additional Bedrooms Complete The Second Level. The Lower Level Offers An Exceptional Extension Of Living Space, Including A Nanny Suite, Oversized Recreation Room, Full Bar, Exercise Room With Ensuite Sauna, Cedar Closet, And A Walk-Up To The Gardens, With Ample Opportunity For Further Customization. Outdoors, The Estate Impresses With A 20' X 40' Pool, Multiple Lounging And Entertaining Areas, An Expansive Stone Terrace, And A Serene Koi Pond, All Enveloped By Lush Landscaping To Ensure Ultimate Privacy. A Rare And Distinguished Offering In One Of The City's Most Coveted Enclaves.
Nearby Intersections
Property Features
Golf, Hospital, Library, Park, School, Auto Garage Door Remote, Central Vacuum, ERV/HRV, Sauna, Steam Room, Water Heater, Circular Drive
Property Details
Address
21 Fifeshire Road
Postal Code
M2L 2G4
Property Type
Detached, Detached
Lot Size
122' x 178'
Taxes
$23,377 (2025
Basement
Walk-Up, Finished
Heat Type
Forced Air
Heat Source
Gas
Water
Municipal
Pool
Inground
Parking Spaces
12
Garage Type
Built-In
Listing contracted with Re/Max Realtron Barry Cohen Homes Inc.
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BEDS
7
BATHS
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4+2
BEDS
7
BATHS
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BEDS
8
BATHS
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FOR SALE
Set on a rare 100-foot frontage along an exclusive, child-safe crescent in Toronto's coveted Bridle Path, this renovated, move-in-ready two-storey blends timeless brick architecture with refined modern interiors. Generously scaled principal rooms feature exotic wood finishes, two fireplaces, and walkouts to sun-filled terraces. The modern centre-island kitchen opens to terrace access, ideal for entertaining, while a main-floor office and breakfast room complete the level. Upstairs, the primary suite offers a five-piece ensuite and walk-in closet, joined by four additional bedrooms, several with private ensuites. The fully finished walk-out lower level is a private retreat with a second kitchen, two bedrooms, a recreation room, a media and billiards room, and a playroom, all brightened by above-grade windows with direct garden access. An ideal in-law or nanny suite. Extensively upgraded approximately one year ago: new roof, two new heating systems, whole-home and kitchen water filtration, exterior security cameras, fresh landscaping with a new front-yard sprinkler system, finished basement with kitchen, new pot lights, new blinds throughout, a new terrace floor, and new terrace lighting. All windows have been replaced across every level, and the full staircase connecting the main, second, and lower levels has been upgraded to hardwood with new railings. A built-in three-car garage with parking for six more completes the offering. Set on beautifully manicured, private grounds, this is Bridle Path living at its finest.
11 Dewbourne Avenue, Toronto
5
BEDS
8
BATHS
$5,660,000
FOR SALE
**Captivating residence/exquisite estate--Classic Elegance--This magical home has been meticulously cared for, remodeled/upgraded, and maintained by its owners--Classic/charm centre hall design offers spaces of refined and elegant comfort--5,511 sq.ft (3 storey) + 1,007 sq.ft (basement)---total 6,518 sq.ft of luxurious--where every impeccable detail has been carefully crafted and preserved. The grand principal rooms are designed for both elegance and comfort, a formal dining room and a living room with marble mantle fireplace. The functional gourmet kitchen is equipped with built-in appliances (Sub-Zero/Wolf brand), custom cabinetry & granite countertops. The adjoining family/sun room features a HEATED LIMESTONE floor and 16 ft high glass ceilings, allowing natural sunlight and French doors walkout to south exposure private garden. Upstairs, the hand-carved antique pine paneled library elaborates a story of this home, perfect for versatile use such as 2nd family room and adjoining a mahogany paneled office for a private space. The primary bedroom offers a dressing room, 6 pcs ensuite. The family gym on 2nd floor offers a 18 ft high ceiling with skylights for convenience and comfort. On 3rd floor, the additional all 3 bedrooms provide their own private ensuites, closets, and feature a 3rd furnace and 2nd laundry area. The lower level offers an entertainment room, music and studio room, wine cellar with climate control. Outside, the landscaped lush garden features cheerful trees for privacy and relaxation, and a heated driveway for 5 vehicles, and 2 cars in garage. Surrounded by top ranking private and public schools-UCC/BSS/Havergal College/Forest Hill Junior & Senior PS & Forest Hill CI. A short walk brings you to Forest Hill Village with shops, restaurants & cafes, minutes to sunway station, hwys & more!
4 Forest Wood, Toronto
5+1
BEDS
7
BATHS
$5,500,000
FOR SALE
Exclusive Bedford Park Enclave. Modern Luxury. Over 5,600 sf Of Living Area. 2-1/2 Storeys With Rare 3rd Floor Great Room And Fully Finished Lower Level With 2nd Kitchen/Wet Bar. This Sun Drenched Residence Is Perfectly Suited For A Large Family Or Those Who Love To Entertain And Values A Child Safe Street Community. The Gourmet Kitchen Features High-End Appliances and Waterfall Centre Island, Imported Italian Marble/Quartzite Countertops, Pot Filler, Well-Appointed Servery And Breakfast Area With Open Concept Layout To The Living Room And Dining Room. The 2nd Floor Boasts 3 Generously Sized Bedrooms With 4-Piece Ensuites And Custom Closets, Plus Primary Retreat Complete With Private Balcony Overlooking The Rear Garden, Luxurious Dressing Room And Lavish 8-Piece Marble Ensuite. Additional Living Spaces Include A Third-Level Great Room With Gas Fireplace And 4-Piece Ensuite Which Can Be Converted To A 6th Bedroom If Needed, A Fully Finished Lower Level With A Spacious Rec Room, Nanny's Suite, Wine Cellar, Laundry Room, 2nd Kitchen/Wet Bar, Lounge And Very Convenient Walk-Up To The Rear Garden. Professional Landscaping and Exterior Lighting Provide Stunning Curb Appeal To The Striking Stone Exterior, Complemented By The Equally Impressive Rear Gardens With Modern Horizontal Wood Fencing And Lush Greenery To Provide The Perfect Backdrop For Your Custom Landscape Design. A Perfect Blend Of High-End Finishes, Expert Design And Modern Comforts!
6 Penwood Crescent, Toronto
5+1
BEDS
7
BATHS
$5,495,000
FOR SALE
Windfields Park feels like an extension of your backyard at this classic red-brick Georgian-inspired luxury family home in Bayview & York Mills. Set on a rare 84' x 125' lot in Banbury/Denlow, 6 Penwood Crescent combines timeless architecture, exceptional scale and remarkable privacy with beautiful park and sunset views. Offering approx. 4,500 Sq. Ft. above grade plus a finished walkout lower level that sits at grade and lives like a true third level, the home has been thoughtfully renovated and improved over the years by the current owners. Inside are 5+1 bedrooms, 7 baths, oversized principal rooms, a renovated eat-in kitchen with centre island and premium appliances, and a spacious family room overlooking the park. Multiple walkouts connect the interiors to generous outdoor entertaining spaces, mature landscaping and an inground pool. Traditional architectural details include custom millwork, panelled walls, mouldings, built-ins, beamed ceilings and a graceful curved staircase. The private principal suite is a serene retreat with tranquil park views, a generous walk-in dressing room/closet with built-in organizers and a spa-inspired 8-piece ensuite with heated marble floors, dual vanities, whirlpool tub and separate glass shower. The at-grade lower level is ideal for entertaining, guests or extended family, with a recreation room, wet bar, cedar wine cellar, sauna and an exercise room easily used as a sixth bedroom or nanny's quarters. Two-zone HVAC, a double built-in garage and private drive complete the home. Minutes to Denlow P.S., Windfields Middle School, York Mills Collegiate, Bayview Glen School, Crescent School, the Granite Club, Donalda Club, parks, Shops at Don Mills, Bayview Village and convenient Hwy 401/DVP access. A rare Toronto luxury home where classic Georgian character, family-friendly space and an extraordinary park setting come together.
75 Truman Road, Toronto
4+1
BEDS
7
BATHS
$5,480,000
FOR SALE
Welcome to Villa Lunaire, an exquisitely renovated residence where timeless sophistication meets resort-inspired living. Set on an extraordinary 60' x 267' private lot, this remarkable estate offers nearly 7,000 sq. ft. of beautifully appointed living space designed for elegant entertaining and exceptional everyday living.Sun-filled principal rooms, professionally curated interiors by Qummunicate, and impeccable craftsmanship create a refined yet inviting atmosphere. The designer kitchen, renovated in 2022, features premium Fisher & Paykel, Bosch, KitchenAid and Marvel appliances, seamlessly connecting to expansive living spaces that overlook the spectacular backyard.Outside, discover a private retreat inspired by the world's finest resorts. A heated 18' x 36' saltwater pool, built-in hot tub, composite entertainment deck, cabana with granite countertop and sink, extensive stone landscaping, landscape lighting, and multiple outdoor entertaining areas create an unforgettable setting for relaxing or hosting beneath the stars.The home offers five spacious bedrooms plus a lower-level guest or nanny suite, 5+2 bathrooms, an attached private two-car garage, and an impressive collection of modern conveniences including Sonos whole-home audio, Lutron smart lighting, comprehensive security systems, a Generac whole-home backup generator, EV charging pre-wire, and numerous recent mechanical updates.Ideally located just moments from Bayview Village, the TTC subway, Crescent School, Toronto French School, Crestwood Preparatory College, Bayview Glen, The Granite Club and Donalda Club, Villa Lunaire offers an exceptional balance of privacy, prestige, and convenience.
652 Bedford Park Avenue, Toronto
4+2
BEDS
7
BATHS
$5,388,888
FOR SALE
A True Architectural Showpiece-presenting one of Bedford Park's most extraordinary newly built luxury homes. This masterfully crafted custom SMART HOME, complete with a private 4-stop elevator, offers over 5,000 Sq.Ft. of flawlessly curated living space across four spectacular levels. Designed with commanding presence and constructed with uncompromising precision-premium facade, high-performance windows, and designer roof-the interiors exude the sophistication and drama of a world-class design publication. Step inside to a main level that captivates instantly: exceptional custom millwork, elegant principal rooms, and an ultra-polished chef's kitchen featuring top-tier Miele appliances, all elevated by a discreet catering kitchen for seamless entertaining. Cutting-edge home automation, integrated systems, and meticulously sourced hardware enhance the home with effortless luxury and modern intelligence. The primary retreat is an oasis of indulgence-a private sanctuary offering a spa-inspired ensuite with radiant-heated marble floors, sculptural freestanding tub, curb less steam/rain shower, and private water closet. Every additional bedroom is complete with its own heated ensuite, creating a five-star experience for family and guests alike. The lower levels redefine luxury living with a sleek recreation lounge and wet bar designed for unforgettable gatherings. A rare sub-basement expands the home's capabilities even further, offering a gym room, guest suite, wine/cold storage, and top-of-the-line mechanicals. Heated floors throughout deliver a continuous sense of warmth, comfort, and refinement. A breathtaking fusion of innovation, artistry, and timeless luxury, this residence transcends expectations-an unmistakable statement of prestige in one of Toronto's most coveted neighborhood's.
177 Coldstream Avenue, Toronto
6+2
BEDS
8
BATHS
$6,822,000
FOR SALE
In the heart of coveted Lytton Park, on a quiet tree-lined street, stands a remarkable architectural residence with a West Coast feel designed for exceptional family living. Set on a rare 218-foot-deep lot, the spectacular grounds by Shirley Den Houdyker Landscaping evoke the tranquility of Muskoka in the city. Privately custom-built by acclaimed Toronto builder Richard Wilson of Wilson Project Management (founder of AGNORA), who was personally referred to the owner by legendary architect Siamak Hariri, following private review of the home's drawings, that was built to museum-grade standards. This 8,000+ sq. ft. residence is a masterclass in craftsmanship & design. Clad in honed, polished & dry-laid Owen Sound ledge rock w/elegant copper detailing, the home showcases timeless architecture & extraordinary attention to detail throughout. Custom mahogany doors & windows, expansive walls of glass, wide-plank walnut floors/ceilings & illuminated walnut staircases with custom hand-built stair railings create a warm yet sophisticated atmosphere. Designed for both entertaining & family living, the home offers 6+2 bedrooms & a dramatic great room overlooks landscaped terraces, a pergola, a Todd Pools-designed pool, a cabana with bath & built-in stone jacuzzi. The Scavolini kitchen features Carrara marble countertops, an oversized island, premium Wolf & Miele multiple XL appliances x2 & a walk-in pantry. The luxurious primary suite incl a private sitting room with a fireplace & a spa-inspired ensuite with heated floors, oversized shower & egg soaker tub. Additional highlights include 4 gas fireplaces, heated stone & tile surfaces, cedar roof, reverse osmosis & soft-water systems, lower-level in-law suite, gym with steam shower, media & recreation rooms, & parking for 3 vehicles. Ideally located near Toronto's finest public & private schools, including JRR P.S., Lawrence Park C.I, Havergal & Day Schools. Close to the financial district. A truly exceptional family residence.
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