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300 Upper Highland Crescent
St. Andrew-Windfields Toronto M2P 1V5

$5,180,000
Residential Freehold beds: 5+2 baths: 8.0

Main Photo: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 1: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 2: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 3: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 4: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 5: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 6: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 7: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 8: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 9: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 10: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 11: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 12: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 13: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 14: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 15: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 16: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 17: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 18: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 19: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 20: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 21: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 22: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 23: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 24: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 25: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 26: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 27: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 28: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 29: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 30: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 31: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 32: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 33: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 34: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 35: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 36: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 37: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 38: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 39: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 40: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 41: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 42: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 43: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 44: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 45: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 46: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 47: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 48: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 49: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Photo 50: 300 Upper Highland Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12)  : MLS®# C12917192
Status:
Active
Prop. Type:
Residential Freehold
MLS® Num:
C12917192
Bedrooms:
5+2
Bathrooms:
8
Nestled in the highly sought-after St. Andrews neighbourhood, surrounded by multi-million dollar estates, this custom-built home (2019)Situated on a premium 75' corner lot overlooking Tournament Park, offering privacy, space, and an abundance of natural light throughout. 4,645 sq ft above grade plus ~2,000 sq ft of professionally finished basement, this residence showcases refined craftsmanship and a thoughtfully designed layout ideal for both family living and elegant entertaining. The main level features 10' ceilings, a grand open-concept layout with formal living and dining rooms, a private home office, and a stunning gourmet chef's kitchen seamlessly connected to a sun-filled family room. A well-appointed mudroom and powder room complete the space. Upstairs offers 9' ceilings and 5 spacious bedrooms, each with access to beautifully designed bathrooms, delivering both comfort and privacy. The bright 9' basement is an entertainer's retreat, featuring a second kitchen/bar, expansive recreation space, 2 bedroom and a sauna, perfect for relaxation and hosting. Step outside to a professionally upgraded backyard, where hundreds of thousands have been invested to create a private outdoor oasis. Minutes to Rosedale Golf Club, Don Valley Golf Course, and the prestigious Granite Club, Convenient access to major routes, shopping, and amenities. Top-Ranked Schools: Owen Public School, St. Andrew's Middle School, York Mills Collegiate Institute. Nearby Private Schools: Crescent School - One of Toronto's top all-boys private schools (Grades 3-12), Toronto French School (TFS) - Leading bilingual IB school (Pre-K to Grade 12), The York School- Renowned IB private school with strong academic reputation, Bayview Glen School - Prestigious co-ed private school (JK-Grade 12), A rare opportunity to own a luxury custom home on an oversized lot in one of Toronto's most prestigious communities. Perfect for discerning buyers seeking space, quality, and top-tier education.
Property Type:
Residential Freehold
Property Sub Type:
Detached
Home Style:
2-Storey
Approx. Age:
0-5
Total Approx Floor Area:
3500-5000
Lot Depth:
110'
Lot Frontage:
75'
Lot Details:
75.00 x 110.00 Feet (Corner Lot)
Direction Faces:
South
Bedrooms:
5+2
Bathrooms:
8.0
Water supply:
Municipal
Kitchens:
2
Kitchens in Basement:
1
Bedrooms Above Grade:
5
Bedrooms Below Grade:
2
Kitchens Above Grade:
1
# Main Level Bedrooms:
0
# Main Level Bathrooms:
0
Rooms Above Grade:
10
Rooms Below Grade:
2
Rooms:
15
Zoning:
Residential
Heating type:
Forced Air
Heating Fuel:
Gas
Cooling:
Yes
Foundation:
Concrete
Roof:
Asphalt Shingle
Basement:
Finished, Separate Entrance
Fireplace/Stove:
Yes
Attached Garage:
Yes
Garage:
Attached
Garage Spaces:
2.0
Parking Features:
Private
Parking Spaces:
2
Total Parking Spaces:
4.0
Family Room:
Yes
Lot Irregularities:
Corner Lot
Pool:
None
Link:
No
HST Applicable To Sale Price:
Not Subject to HST
Taxes:
$25,322.24 / 2025
Assessment:
$- / -
Toronto
Toronto C12
St. Andrew-Windfields
Park
Irregular Lot
Ventilation System
Hot water tank
fridge, stove, washer, dryers, dishwasher, existing electrical light features, existing window coverings.
Brick, Stone
No
Floor
Type
Size
Other
Second
Primary Bedroom
26'3" × 15'8"
5 Pc Ensuite, Walk-In Closet(s), Hardwood Floor
Second
Bedroom 2
13'5" × 12'9½"
Walk-In Closet(s), Window, 4 Pc Bath
Second
Bedroom 3
12'9½" × 11'7"
Window, 3 Pc Bath, Walk-In Closet(s)
Second
Bedroom 4
15'3" × 11'9¾"
Hardwood Floor, 4 Pc Bath, Closet
Second
Bedroom 5
16'5" × 13'3"
3 Pc Bath, Double Closet, Hardwood Floor
Main
Family Room
15'5" × 15'1"
B/I Bookcase, Gas Fireplace, Hardwood Floor
Main
Kitchen
23'3½" × 8'6"
B/I Appliances, Hardwood Floor, Breakfast Area
Main
Dining Room
14'5¼" × 13'9"
Hardwood Floor, Bay Window, Combined w/Living
Main
Living Room
17'1" × 13'1½"
Gas Fireplace, Bay Window, Hardwood Floor
Main
Office
11'9¾" × 11'3"
B/I Bookcase, Hardwood Floor, Window
Basement
Recreation
39'4½" × 15'1"
Heated Floor, Porcelain Floor, B/I Appliances
Basement
Bedroom
15'3" × 12'6"
4 Pc Bath, Closet, Heated Floor
UFFI:
No
Special Designation:
Unknown
Sewers:
Sewer
Air Conditioning:
Central Air
Central Vacuum:
No
Seller Property Info Statement:
No
Laundry Level:
Upper Level
Date Listed:
Mar 24, 2026
Original Price:
Previous Price:
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Listed by ROYAL ELITE JERRY WEN REALTY INC.
Data was last updated March 25, 2026 at 04:15 AM (UTC)
Area Statistics
Listings on market:
62
Avg list price:
$4,443,000
Min list price:
$1,699,000
Max list price:
$18,000,000
Avg days on market:
50
Min days on market:
1
Max days on market:
414
These statistics are generated based on the current listing's property type and located in St. Andrew-Windfields. Average values are derived using median calculations. This data is not produced by the MLS® system.
JARROD  ARMSTRONG
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.