Proudly Canadian
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 1 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 2 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 3 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 4 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 5 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 6 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 7 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 8 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 9 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 10 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 11 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 12 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 13 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 14 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 15 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 16 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 17 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 18 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 19 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 20 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 21 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 22 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 23 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 24 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 25 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 26 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 27 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 28 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 29 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 30 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 31 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 32 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 33 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 34 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 35 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 36 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 37 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 38 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 39 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 40 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 41 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 42 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 43 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 44 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 45 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 46 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 47 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 48 of 49
Detached for sale at 300 Upper Highland Crescent, Toronto C12 - 7 bedroom, 8 bathroom - Photo 49 of 49
1 / 4946 locked
View on map
Active

$4,390,000

300 Upper Highland Cres

Toronto C12, ON M2P 1V5

300 Upper Highland Cres, Toronto C12Listed at $4,390,000. 7 bedroom, 8 bathroom 2-Storey Detached. MLS® C13716590.

Possession · seller's timeline

Immediate

7Beds
8Baths
3500-5000sqft
Detached
2-Storey
4Parking
$25,766.31Taxes/yr · 2026

What's this home worth?

Get a free estimate for 300 Upper Highland Cres

Description

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 Details

Property TypeDetached
Style2-Storey
CommunitySt. Andrew-Windfields
Approximate Age0-5
Rooms10+2
Kitchens2
Washrooms8
Square Feet3500-5000 sqft
Lot Dimensions75 × 110 ft
Fronting OnSouth
Dir/Cross StYonge/York Mills
Garage TypeAttached
Garage Parking Spaces2
DrivePrivate
Parking Drive Spaces2
Total Parking Spaces4
ExteriorBrick, Stone
RoofAsphalt Shingle
FoundationConcrete
BasementFinished, Separate Entrance
Fireplace FeaturesYes
Heating TypeForced Air
Heating SourceGas
A/CCentral Air
SewersSewer
Taxes (2026)$25,766.31
HSTNot Subject to HST
UFFINo
Listed Date8/27/2026
Days on Market9 days

Virtual Tour

Explore from home

Same-day showings available
5.0Rated 5 stars on Google ReviewsWhatsApp Us About This Listing

Property Insights

Home Value
Estimate

Listing Courtesy of: ROYAL ELITE JERRY WEN REALTY INC.

MLS® #C13716590

TRREBMLS®

The listing data is provided under copyright by the Toronto Regional Real Estate Board (TRREB). The listing data is deemed reliable but is not guaranteed accurate by TRREB. The trademarks REALTOR®, REALTORS®, and the REALTOR® logo are controlled by The Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by CREA and identify the quality of services provided by real estate professionals who are members of CREA. Used under license.

© 2026 Toronto Regional Real Estate Board. All rights reserved.

Thinking about living in Toronto?

Explore the neighbourhood guide for Toronto — market trends, popular areas, buyer tips, and more.

HouseIndex Take: 300 Upper Highland Crescent

This detached (2-Storey) is located in the St. Andrew-Windfields neighbourhood of Toronto.

The home offers 7+2 bedrooms, 8 bathrooms.

Features include a finished, separate entrance basement, 4 parking spaces including a 2-car garage, a fireplace.

Additional details: lot dimensions of 75 × 110 feet.

Listed at $4,390,000 CAD with annual property taxes of $25,766.31 (2026).

About Toronto Real Estate

This Detached is located in the St. Andrew-Windfields community in Toronto. Toronto is Canada's largest city and the economic hub of the Greater Toronto Area. With world-class transit, diverse neighbourhoods from the Annex to Scarborough, and proximity to major employers in the Financial District, it remains the most sought-after real estate market in Ontario. Buyers benefit from extensive GO Transit and TTC subway connectivity. Detached homes in Toronto are in high demand among families seeking space, privacy, and long-term equity growth.

TTC subway & streetcar networkWorld-class dining & entertainmentUniversity of Toronto & major hospitals nearbyWaterfront trails & ravine parks
Walkability: Highly walkable — many neighbourhoods score 80+ on Walk Score
View full Toronto neighbourhood guide →