Fifeshire homes for sale & real estate

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OPEN SAT, 2PM TO 4PM

ABOUT THIS HOME
Fifeshire Homes for Sale
Welcome To This Prestigious Executive Residence In The Heart Of York Mills, Offering A Rare Opportunity To Own A Stunning Luxury Home On One Of The Area's Most Sought-After Streets. This Exceptional Home Features Grand Principal Rooms, Soaring Ceilings, Elegant Mouldings, And Timeless Architectural Details Throughout. The Expansive Chef's Kitchen Opens To A Sun-Filled Breakfast Area And Family Room, Creating The Perfect Space For Everyday Living And Entertaining. The Main Level Also Offers Formal Living And Dining Rooms, A Private Office, And Beautiful Views Of The Manicured Grounds. Upstairs, The Spacious Primary Suite Features A Spa-Inspired Ensuite And Custom Walk-In Closets, Along With

$6,998,000

7 beds7 baths— sq ft

9 Fifeshire Rd, North York, ON M2L 2G4

Private office • Luxury home • Executive residence

ABOUT THIS HOME
Fifeshire Homes for Sale
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. Gr

$7,500,000

6 beds8 baths— sq ft

21 Fifeshire Rd, North York, ON M2L 2G4

Grand foyer • 0.5 acre lot • Garage

ABOUT THIS HOME
Fifeshire Homes for Sale
Stunning Custom Residence, Windermere Homes Built On A Quiet Exclusive Cul-De-Sac In Prestigious Family-Friendly Neighbourhood of St. Andrew-Windfields. 187' Of Frontage, Soaring Ceilings, Crown Moulding, Integrated Speakers, And Luxurious Finishes Throughout. Generously-Sized Principal Rooms Overlooking The Serene Rear Rock Garden Set Against A Lush Verdant Landscape. Open Concept Gourmet Kitchen With Breakfast Area And Family Room Features Custom Finishes, Cathedral Ceiling And Sun-Drenched Interior With Walkouts To The Sprawling Side Garden. The Tranquil Primary Retreat Features Ante-Room Entrance, Vaulted Ceiling, Sitting Area With Custom Fireplace, Walk-In Closet, And Lavish 8-Piece En

$4,998,000

5 beds6 baths— sq ft

3 Legacy Crt, North York, ON M2L 2Y7

Custom fireplace • Exclusive cul-de-sac • Sprawling rec room

ABOUT THIS HOME
Fifeshire Homes for Sale
Completely Renovated!This Attractive Residence Is Nestled On Tranquil Professionally Landscape Garden Setting In One Of Toronto's Finest Areas. Featuring Over 20 Feet Ceiling In Living Room Overlooking Backyard With Open Concept. Unique Loft At Top Floor, Gourmet Kitchen With Granite Central Island Counter Top, Built In Appliances. Second Kitchen in main floor, Office With Wet Bar, Sauna, Jacuzzi, Walk Out Basement With Wet Bar And Fireplace. professionally designed back yard with Pool.

$9,380,000

7 beds8 baths— sq ft

19 Fifeshire Rd, North York, ON M2L 2G4

Sauna • Second kitchen • Gourmet kitchen

ABOUT THIS HOME
Fifeshire Homes for Sale
This spectacular, custom-crafted, architecturally designed 24-year-new residence is nestled on a quiet cul-de-sac in the prestigious St. Andrew-Windfields family-friendly neighborhood. Situated on a 270 ft wide private treed lot (15,750 sqft) with park-like yards, it offers over 6,500 square feet of luxurious living space, including a 1,670 sqft separate-entrance basement. This home features a striking four sides stone exterior and soaring ceilings. A circular iron staircase anchors the elegant interior, where every bedroom includes its own ensuite bathroom. The spacious primary suite offers a large sitting area and a 6-piece ensuite, while the second-floor laundry room adds daily convenien

$4,990,000

5 beds7 baths— sq ft

7 Legacy Crt, North York, ON M2L 2Y7

Private treed lot • Quiet cul de sac • Ensuite bathroom

ABOUT THIS HOME
Fifeshire Homes for Sale
A rare legacy estate awaits! Seize the opportunity to build your dream home on one of Toronto's most prestigious streets. Nestled in the heart of the coveted Bayview and York Mills enclave, 38 Fifeshire Road presents an exceptional offering to create a bespoke masterpiece in one of the city's most distinguished neighbourhoods. Spanning nearly 1/2 an acre, this expansive ravine lot is a canvas of serenity and prestige, framed by lush greenery, mature trees, and the tranquil beauty of its natural surroundings. With exceptional frontage, depth, and breathtaking ravine vistas, this property is a dream for visionary architects and discerning homeowners. The existing residence, boasting nearly 5,

$4,995,000

5 beds5 baths— sq ft

38 Fifeshire Rd, North York, ON M2L 2G6

Outdoor terraces • Lush greenery • Ravine lot

Property at 2638A Bayview Ave, North York, ON M2L 1B7, 4 beds, 4 baths

$2,850,000

4 beds4 baths— sq ft

2638A Bayview Ave, North York, ON M2L 1B7

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OPEN SAT, 3PM TO 5PM

ABOUT THIS HOME
Fifeshire Homes for Sale
An Exceptional Recently Built Custom Residence By Casa Unique Homes, Set On A Quiet Dead-End Street In Prestigious York Mills. Offering Approximately 6,300 Sq. Ft. Of Impeccably Crafted Living Space, This Remarkable Home Is A Showcase Of Timeless Architecture, Bespoke Detailing, And Sophisticated Contemporary Design. A Striking Limestone Facade And Handcrafted Mahogany Entry Introduce Interiors Defined By Soaring Ceilings, Wide-Plank Oak Floors, And A Private Elevator Connecting All Levels. Extraordinary Finishes Include A Sculptural Custom Staircase With 14K Gold Accents, Marble Foyer With Brass Inlay, And Exquisite Stonework Throughout. Grand Principal Rooms Flow Effortlessly For Both Ele

$5,998,000

5 beds8 baths— sq ft

148 Munro Blvd, North York, ON M2P 1C8

Marble foyer • Limestone facade • Private elevator

ABOUT THIS HOME
Fifeshire Homes for Sale
A Rare Opportunity In One Of St. Andrew-Windfields' Most Desirable And Quiet Pockets. Set On An Impressive Lot Backing Onto A Beautiful Treed Green Space, This Home Offers Exceptional Privacy, Peaceful Views And A Wonderful Sense Of Seclusion. Located In The Highly Sought-After York Mills/Bayview Community, Close To Excellent Schools, Parks, Transit, Highway 401, Bayview Village, Shops, Restaurants And Everyday Amenities. Offering 5+1 Bedrooms And 4 Bathrooms, The Home Features Generous Principal Rooms, Multiple Living Spaces Overlooking The Greenery, A Spacious Kitchen And Family Room, And A Primary Suite With Peaceful Rear Views. The Finished Walk-Out Lower Level Provides A Large Recreati

$3,400,000

6 beds4 baths— sq ft

30 Medalist Rd, North York, ON M2P 1Y5

Spacious kitchen • Impressive lot • Exceptional privacy

ABOUT THIS HOME
Fifeshire Homes for Sale
Welcome to this spectacular custom-built residence offering approx. 6,150 sq. ft. across 3 levels on a premium. A timeless limestone façade, soaring ceilings and exceptional craftsmanship define this impressive home. The grand foyer and private office feature 13'4" ceilings, with 9.5' on the main floor, 10' on the second and 11'6" in the basement. The open-concept living, dining, family room and gourmet kitchen create an impressive setting for living and entertaining. The elegant living room features a dramatic bookmatched natural-stone feature wall and fireplace. The chef's kitchen boasts marble countertops, matching backsplash, Sub-Zero, Wolf & Miele appliances, a 9

$3,288,000

7 beds7 baths— sq ft

15 Calvin Ave, North York, ON M2N 5E4

Open concept living • Private office • Limestone facade

ABOUT THIS HOME
Fifeshire Homes for Sale
* * * PRIDE OF OWNERSHIP * * * Welcome to 158 Owen Blvd. This elegant & owner's own custom-built residence boasts blend of sophistication and warmth with exquisite materials thru-out and beautiful home nestled in a highly sought-after, prestigious St Andrew neighbourhood. This UNIQUE architectural masterpiece offers approximately 7000 sf luxurious living space(4800 sf for 1st/2nd floors), meticulously-maintained by its, original owner, to capture tranquil-private views of backyard. The main floor offers an expansive living & dining space, ideal for entertaining or relaxing at home with airy atmosphere and grand & open-feel. The gourmet kitchen is equipped with built-in

$4,888,000

6 beds6 baths— sq ft

158 Owen Blvd, North York, ON M2P 1G7

Gourmet kitchen • Outdoor deck • Patio

ABOUT THIS HOME
Fifeshire Homes for Sale
Renovated in 2025, this updated 3-bedroom, 2-bathroom suite offers over 1,000 sqft of efficient, well-planned living in the highly connected Willowdale East area, designed for buyers who prioritize everyday convenience and a low-maintenance lifestyle in the heart of North York. Fresh improvements including new flooring, modern vanities, fresh paint, and updated light fixtures create a clean, move-in ready space that supports a streamlined, no-fuss way of living. The bright combined living and dining area extends to a large private balcony overlooking quiet landscaped grounds and stunning western views, offering a simple outdoor escape without leaving home. The functional kitchen features cl

$565,000

3 beds2 baths— sq ft

20 Fashion Roseway N/A #408, North York, ON M2N 6B5

Functional kitchen • Landscaped grounds • Private balcony

3D WALKTHROUGH

ABOUT THIS HOME
Fifeshire Homes for Sale
Rarely Offered Ground Floor 2 Bedroom Suite In Sought-After Bayview Place Condominiums. Vibrant Uptown North York Locale Steps To nearby park, TTC/Subway, Boutique Shops, and Restaurants. Quick Commute To Downtown Toronto. Laminate Floors In the living-dining room, Foyer, Hallway & Primary Bdrm. Kitchen with Glass tile back-splash. Granite counter in bathroom. In-suite Laundry and storage locker. This bright and spacious unit offers 9' ceilings, and a combined living-dining room with Walk-Out To Patio facing the courtyard. Enjoy Breakfast In The Sun On Your Own Private Patio surrounded by greenery. A truly rare find!

$499,990

2 beds1 bath— sq ft

20 Fashion Roseway N/A #105, North York, ON M2N 6B5

In-suite laundry • Nearby park • Storage locker

Property at 1 Rean Dr #1606, North York, ON M2K 3C1, 2 beds, 2 baths

$538,888

2 beds2 baths— sq ft

1 Rean Dr #1606, North York, ON M2K 3C1

Property at 48 Berkindale Dr, North York, ON M2L 1Z8, 8 beds, 7 baths

$3,645,000

8 beds7 baths— sq ft

48 Berkindale Dr, North York, ON M2L 1Z8

Property at 164 Munro Blvd, North York, ON M2P 1C8, 5 beds, 3 baths

$2,898,000

5 beds3 baths— sq ft

164 Munro Blvd, North York, ON M2P 1C8

Property at 122 Fenn Ave, North York, ON M2P 1X6, 4 beds, 4 baths

$2,250,000

4 beds4 baths— sq ft

122 Fenn Ave, North York, ON M2P 1X6

Property at 115 Scenic Mill Way, North York, ON M2L 1T1, 4 beds, 3 baths

$990,000

4 beds3 baths— sq ft

115 Scenic Mill Way, North York, ON M2L 1T1

Property at 10 Brassbell Mill Way, North York, ON M2L 1P7, 3 beds, 3 baths

$749,000

3 beds3 baths— sq ft

10 Brassbell Mill Way, North York, ON M2L 1P7

Property at 26 Danville Dr, North York, ON M2P 1J1, 6 beds, 7 baths

$4,790,000

6 beds7 baths— sq ft

26 Danville Dr, North York, ON M2P 1J1

Property at 64 Montressor Dr, North York, ON M2P 1Z4, 5 beds, 6 baths

$3,680,000

5 beds6 baths— sq ft

64 Montressor Dr, North York, ON M2P 1Z4

Property at 21 Forest Heights Blvd, North York, ON M2L 1G4, 6 beds, 7 baths

$5,998,000

6 beds7 baths— sq ft

21 Forest Heights Blvd, North York, ON M2L 1G4

Property at 164 Owen Blvd, North York, ON M2P 1G7, 5 beds, 5 baths

$4,390,000

5 beds5 baths— sq ft

164 Owen Blvd, North York, ON M2P 1G7

Property at 1 Rean Dr #2503, North York, ON M2K 3C1, 3 beds, 2 baths

$599,000

3 beds2 baths— sq ft

1 Rean Dr #2503, North York, ON M2K 3C1

Property at 34 Medalist Rd, North York, ON M2P 1Y5, 5 beds, 8 baths

$10,995,000

5 beds8 baths— sq ft

34 Medalist Rd, North York, ON M2P 1Y5

Property at 135 Scenic Mill Way #102, North York, ON M2L 1T1, 3 beds, 3 baths

$1,059,999

3 beds3 baths— sq ft

135 Scenic Mill Way #102, North York, ON M2L 1T1

Property at 11 Montressor Dr, North York, ON M2P 1Y9, 5 beds, 4 baths

$3,050,000

5 beds4 baths— sq ft

11 Montressor Dr, North York, ON M2P 1Y9

Average home prices near Fifeshire, ON

Neighborhoods

Scarborough homes for sale
$744,500
North York homes for sale
$785,000
Uptown homes for sale
$1,095,000
Bathurst Manor homes for sale
$1,126,000
Bayview Village homes for sale
$734,440
Willowdale homes for sale
$689,000
Bedford Park homes for sale
$1,724,500
Bridle Path homes for sale
$10,487,500
Lawrence Park homes for sale
$3,025,000
Don Mills homes for sale
$1,099,440

Fifeshire, ON real estate trends

$800K

Sale price

-92.6%
since last year

—

Sale $/sq ft

Over list price

0.1%

Days on market

218

Down payment

—

Total homes sold

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Source: Statistics Canada, Census Divisions and Census Subdivisions, December 2018. Reproduced and distributed on an "as is" basis with the permission of Statistics Canada.

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