Front of 300 Upper Highland Crescent

300 Upper Highland Crescent

North York (St. Andrew-Windfields)
Terminated
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Ontario Real Estate › North York › St. Andrew-Windfields
Front of 300 Upper Highland Crescent

300 Upper Highland Crescent

North York (St. Andrew-Windfields)
Terminated
See all 49 photos
DetachedMLS C13468722
Last asked:Terminated Aug 21, 2026
$4,680,000
5+2 Bedrooms
8 Bathrooms
2 Garage
3.5K~5K Sq.Ft.
75 x 110 ft Lot
$25,766 Tax/yr

Property history

$5,180,000first asked
$4,390,000last asked
▼ 15%since March
MarMayJulSep
TerminatedSep 1, 2026
$4,390,000MLS® C13716590
Listed for saleAug 26, 2026
$4,390,000MLS® C13716590
TerminatedAug 21, 2026
$4,680,000MLS® C13468722
Listed for saleJun 19, 2026
$4,680,000MLS® C13468722
TerminatedJun 19, 2026
$4,780,000MLS® C13050454
Listed for saleApr 27, 2026
$4,780,000MLS® C13050454
TerminatedApr 27, 2026
$5,180,000MLS® C12917192
Listed for saleMar 24, 2026
$5,180,000MLS® C12917192

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About this home

300 Upper Highland Crescent, North York

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.

Ventilation SystemPark

Facts & features

TypeDetached
Style2-storey
Built0-5
Size3.5K~5K Sq.Ft.
Lot75 x 110 ft
Tax$25,766 (2026)
HeatingForced air, gas
CoolingCentral air
BasementFinished, separate entrance
Parking2 drive
WaterMunicipal
FireplaceYes

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Rooms

12 rooms · 8 bathrooms
Main floor5 rooms
  • Family room15′5″ × 15′1″233 sq.ft.
  • Office11′10″ × 11′3″133 sq.ft.
  • Living room17′1″ × 13′1″224 sq.ft.
  • Dining room14′5″ × 13′9″199 sq.ft.
  • Kitchen23′4″ × 8′6″197 sq.ft.
Second floor5 rooms
  • Bedroom 213′5″ × 12′10″172 sq.ft.
  • Bedroom 311′7″ × 12′10″148 sq.ft.
  • Bedroom 516′5″ × 13′3″217 sq.ft.
  • Primary bedroom15′8″ × 26′3″412 sq.ft.
  • Bedroom 415′3″ × 11′10″180 sq.ft.
Basement2 rooms
  • Bedroom12′6″ × 15′3″190 sq.ft.
  • Recreation39′4″ × 15′1″594 sq.ft.
Bathrooms8
5-pcSecond4-pcSecond4-pcSecond4-pcBasement4-pcBasement3-pcSecond3-pcSecond2-pcMain
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Around this home

Yonge/York Mills
4Walking

Schools nearby

School rating, out of 10.

Avondale Alternativeelementary · Public · 0.9 km
10.0/10
Avondaleelementary · Public · 0.9 km
6.8/10
St Anne Catholicelementary · Catholic · 1.4 km
7.6/10

Listing details

MLS® numberC13468722
Listed onJun 19, 2026
Days on market63
UpdatedAug 21, 2026
Listing brokerageROYAL ELITE JERRY WEN REALTY INC.
Possession2026-07-30 / Flexible

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