300 Upper Highland Crescent, Toronto, ON
St. Andrew-Windfields, Toronto · MLS® C13468722
About this home
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.
Key facts
- Property type
- Detached, 2-Storey
- MLS®
- C13468722
- Bedrooms
- 7 (5 + 2)
- Bathrooms
- 8 (1 half)
- Size
- 3500-5000
- Lot
- 75 × 110 ft
- Cross streets
- Yonge/York Mills
- Parking
- 2 garage · 4 parking (attached)
- Driveway
- Private
- Basement
- Finished, Separate Entrance
- Kitchens
- 2 (1 + 1)
- Heating
- Forced Air
- A/C
- Central Air
- Exterior
- Brick, Stone
- Foundation
- Concrete
- Roof
- Asphalt Shingle
- Sewer
- Sewer
- Property tax
- $25,766 / 2026
- Days on market
- 33
- Listing brokerage
- ROYAL ELITE JERRY WEN REALTY INC.
Rooms
b/i bookcase · gas fireplace · hardwood floor
b/i bookcase · hardwood floor · window
walk-in closet(s) · window · 4 pc bath
4 pc bath · closet · heated floor
window · 3 pc bath · walk-in closet(s)
gas fireplace · bay window · hardwood floor
3 pc bath · double closet · hardwood floor
hardwood floor · bay window · combined w/living
b/i appliances · hardwood floor · breakfast area
heated floor · porcelain floor · b/i appliances
5 pc ensuite · walk-in closet(s) · hardwood floor
hardwood floor · 4 pc bath · closet
Listed at $4,680,000, this home is about 34% above what comparable homes suggest. The number above is my independent estimate of value, not the asking price.
Priced above comparable homes overall, but the price per square foot ($1,101/sqft) is below the area, so you are paying for extra space rather than a premium.
In St. Andrew-Windfields lately, sellers have been getting about 96% of asking and homes sell in about 33 days.
Based on 68 similar homes that recently sold nearby, adjusted for size, beds, and baths.Median of 68 recently sold comparable homes — actual closing prices, not asks — adjusted for size, beds, and baths. The city (MPAC) assessment points to about $4.42M, higher than the comparables and worth a second look. The comparable range is wide here, so treat this as a rough read until I run a full CMA.
How I got there
Here is the exact math behind the estimate. I start from the closest comparable listing and adjust for the real differences (size, beds, baths) to land on a like-for-like value for this home.
- Closest comparable, sold for $2.45M
- Bedrooms +$60K
- Bathrooms +$60K
- Adjusts to $2.57M
That comparable adjusts to $2.57M; the $3.50M estimate above is the median of all 68 comparables, which is steadier than any single home.This estimate is grounded in actual closing prices from the last 15 months, not asking prices. Lot, condition, and finishes are still my in-person call.
On schools, this address is zoned for York Mills Collegiate Institute, one of the higher-rated public schools in the area. A strong catchment tends to hold value and widen your resale pool, especially with family buyers.
Total price vs nearby homes. Fair value about $3.50M, median of 68 comparables.
What the listing highlightsThese are claims from the listing. The only way to know for sure is to see it in person, and I am happy to book you a private showing.
- Finished basement: added living space, worth checking ceiling height and that the work was permitted. Value driver
- Upscale kitchen: a genuine value driver, verify the appliances, stone, and finishes in person. Value driver
- Tall ceilings: they transform how a home feels, worth confirming the actual heights room to room. Worth verifying
- Open-concept layout: modern, sought-after flow. Lifestyle
- Sold as-is / needs work: budget for renovation, the price should reflect the condition. Weigh carefully
The closest active listings by size, beds, and price, so you can see what this home is up against.
The 5 closest of 7 active listings nearby.
See all comparable homesThis home lists 13% below the area average of $1,270/sqft.
32 days longer than the Toronto average (1 days).
View comparable listingsPrice per square foot vs the area average.
Neighbourhood & location
St. Andrew-Windfields, Toronto, ON
Enter a workplace or destination and we’ll show the door-to-door time by car, transit and bike.
How asking prices compare in the closest areas to this home. Longer bars mean a pricier market.
Typical asking price of active listings of the same type, per area (outliers removed). Toronto.
Get the full neighbourhood report (schools, parks, transit & safety) →
The public and Catholic schools this address is zoned for, with EQAO results (the share of students meeting Ontario's provincial standard).
School attendance boundaries and EQAO results are Ontario government data and can change. Confirm the current catchment with the school board before relying on it.
Affordability & Mortgage
Income needed assumes a ~32% GDS ratio; weekly is mortgage principal & interest only. Price ÷ income is the home price over the income needed. Fixed reference assumptions so listings compare on equal footing, not a lending decision.
Calculate and customize your mortgage and other expenses
Adjust the down payment, rate, and amortization, and add property tax, condo fees, and heating to see your true monthly cost.
Your numbers
Homes over $1.5M can't be insured, so 20% down or more is required.
Conventional (20%+ down). Best insured 5-year fixed 3.99% via Ratehub.ca (as of July 23, 2026); conventional rates run a little higher.
Mortgage amount $3,744,000 · 4.14% over 25 years
Total monthly cost
- Mortgage payment (monthly equivalent)
- $19,979
- Property tax
- $2,147
- Condo / maintenance fees
- $0
- Heating
- $0
- Estimated monthly cost
- $22,127
Add your own property tax, condo fees, and heating on the left for a sharper total.
One-time closing costs
- Ontario land transfer tax
- $103,475
- Toronto municipal land transfer tax
- $127,075
- Estimated closing costs
- $230,550
Plus your down payment of $936,000. Legal fees, title insurance, and adjustments are extra and vary by deal.
Mortgage stress test
Lenders qualify you at the greater of your rate plus 2% or 5.25%. You do not pay this rate. It just shows you could still handle payments if rates rose, so aim to stay comfortable at this higher number.
Over the full 25 years
At the end of your 5-year term
- Total paid over the term
- $1,198,762
- Principal paid down
- $476,799
- Interest paid
- $721,963
- Balance remaining
- $3,267,201
Talk to Team Asgarian about your options
Rates and programs change often. We will connect you with a trusted mortgage professional and build a plan that fits your budget and goals.
Estimates only, not a mortgage quote or pre-approval. Figures use Canadian semi-annual compounding, current minimum down-payment rules, CMHC premium tiers, and Ontario (plus Toronto, when selected) land transfer tax. Actual rates, taxes, insurance, and closing costs vary by lender and property. Confirm every number with your mortgage professional.
Investor snapshot
Income potential: the basement has a separate entrance, which often supports a rentable in-law or second suite. That can lift real rent well above the figure above and help carry the mortgage. Ask us about permitted use in this area.
Thinking of this home as an investment? We will pull real comparable rents and run the full numbers with you.
Talk about the numbersEstimates only. Rent is modelled on above-grade size and local norms, so a finished basement or second suite (a separate entrance often means one) can push real rent well above this. Taxes, fees, and vacancy vary by property, and cap rate is before financing. A starting point, not a final number, let us run the real ones with you.
Helpful resources
All information deemed reliable but not guaranteed. For personal, non-commercial use only. Listing courtesy of ROYAL ELITE JERRY WEN REALTY INC.. MLS®/PropTx.