29 Highbourne Avenue, Toronto C02

Price: $2,283,600

4 bedrooms, 3 bathrooms

1,100 - 1,499 sqft

Property Type: Detached

MLS#: C13658016

An unrivalled real estate opportunity in prestigious Forest Hill South, 29 Highbourne Rd balances the British Influence Colonial Revival architectural character with extraordinary future development potential. Positioned prominently near the corner of Highbourne Rd and Oxton Ave, this elegant residence offers a rare foothold in one of Toronto's most exclusive enclaves, commanding unique street exposure that presents lucrative long-term expansion options or premium land value within a blue-chip postal code. Beyond its unique prosperity, the property provides immediate access to Canada's elite educational institutions, situated just steps from the Upper Canada College campus, minutes to BSS and high rank Brown Junior Public School district. The surroundings foster a luxurious urban lifestyle, where the natural serenity of Beltline Trail, Oriole Park, and tranquil ravine systems seamlessly pair with unmatched connectivity, placing the upscale boutiques, fine dining, both Davisville and Yonge & St. Clair subway stations just minutes away. Private driveway and detached garage for easy parking. Symmetrical facades and striking black door and window fenestrations create a balanced, graceful architectural presence. Black iron fence wraps around the front garden enhance the curb appeal. Versatile 3-bed 3-bath layout features a rare main-floor bedroom with a heated-floor ensuite, complemented by two bright upper-level retreats including a principal suite with a walk-in closet and built-in organizers. Seamlessly blending period artistry with modern comfort, the renovated interior shines with rich hardwood, classic wainscoting, crown moldings, and a stately bay window, alongside contemporary refinements featuring a gas fireplace, ambient pot lights, stone countertops, marble backsplash, and sleek basement bathroom. Flowing effortlessly to a private back deck, this home is as perfect for sophisticated family residence today as it is for visionary redevelopment tomorrow.

29 Highbourne Avenue - Detached photo 1 of 33 in Annex / Yorkville / Summerhill, Ontario
29 Highbourne Avenue - Detached photo 2 of 33 in Annex / Yorkville / Summerhill, Ontario
29 Highbourne Avenue - Detached photo 3 of 33 in Annex / Yorkville / Summerhill, Ontario
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29 Highbourne Avenue - Detached photo 5 of 33 in Annex / Yorkville / Summerhill, Ontario
29 Highbourne Avenue - Detached photo 6 of 33 in Annex / Yorkville / Summerhill, Ontario
29 Highbourne Avenue - Detached photo 7 of 33 in Annex / Yorkville / Summerhill, Ontario
29 Highbourne Avenue - Detached photo 8 of 33 in Annex / Yorkville / Summerhill, Ontario
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29 Highbourne Avenue - Detached photo 11 of 33 in Annex / Yorkville / Summerhill, Ontario
29 Highbourne Avenue - Detached photo 12 of 33 in Annex / Yorkville / Summerhill, Ontario
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29 Highbourne Avenue - Detached photo 17 of 33 in Annex / Yorkville / Summerhill, Ontario
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29 Highbourne Avenue - Detached photo 20 of 33 in Annex / Yorkville / Summerhill, Ontario
29 Highbourne Avenue - Detached photo 21 of 33 in Annex / Yorkville / Summerhill, Ontario
29 Highbourne Avenue - Detached photo 22 of 33 in Annex / Yorkville / Summerhill, Ontario
29 Highbourne Avenue - Detached photo 23 of 33 in Annex / Yorkville / Summerhill, Ontario
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29 Highbourne Avenue - Detached photo 27 of 33 in Annex / Yorkville / Summerhill, Ontario
29 Highbourne Avenue - Detached photo 28 of 33 in Annex / Yorkville / Summerhill, Ontario
29 Highbourne Avenue - Detached photo 29 of 33 in Annex / Yorkville / Summerhill, Ontario
29 Highbourne Avenue - Detached photo 30 of 33 in Annex / Yorkville / Summerhill, Ontario
29 Highbourne Avenue - Detached photo 31 of 33 in Annex / Yorkville / Summerhill, Ontario
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$2,283,600 - 29 Highbourne Avenue, Yorkville

Detached for Sale in Yorkville

Popular Listing

Neighbourhood: Yonge-St. Clair

4Beds
3Baths
1,100 - 1,499Sq Ft
Detached
Property Details
MLS Number
C13658016
Property Type
Detached
Status
active
Days on Site
13
Bedrooms
4
Bathrooms
3
Square Feet
1,100 - 1,499 sqft
Neighbourhood
Annex / Yorkville / Summerhill
Listing Brokerage
SOTHEBY'S INTERNATIONAL REALTY CANADA
Description

An unrivalled real estate opportunity in prestigious Forest Hill South, 29 Highbourne Rd balances the British Influence Colonial Revival architectural character with extraordinary future development potential. Positioned prominently near the corner of Highbourne Rd and Oxton Ave, this elegant residence offers a rare foothold in one of Toronto's most exclusive enclaves, commanding unique street exposure that presents lucrative long-term expansion options or premium land value within a blue-chip postal code. Beyond its unique prosperity, the property provides immediate access to Canada's elite educational institutions, situated just steps from the Upper Canada College campus, minutes to BSS and high rank Brown Junior Public School district. The surroundings foster a luxurious urban lifestyle, where the natural serenity of Beltline Trail, Oriole Park, and tranquil ravine systems seamlessly pair with unmatched connectivity, placing the upscale boutiques, fine dining, both Davisville and Yonge & St. Clair subway stations just minutes away. Private driveway and detached garage for easy parking. Symmetrical facades and striking black door and window fenestrations create a balanced, graceful architectural presence. Black iron fence wraps around the front garden enhance the curb appeal. Versatile 3-bed 3-bath layout features a rare main-floor bedroom with a heated-floor ensuite, complemented by two bright upper-level retreats including a principal suite with a walk-in closet and built-in organizers. Seamlessly blending period artistry with modern comfort, the renovated interior shines with rich hardwood, classic wainscoting, crown moldings, and a stately bay window, alongside contemporary refinements featuring a gas fireplace, ambient pot lights, stone countertops, marble backsplash, and sleek basement bathroom. Flowing effortlessly to a private back deck, this home is as perfect for sophisticated family residence today as it is for visionary redevelopment tomorrow.

Mortgage Calculator

Estimate your monthly payments for this property

Estimated Payment

$10,101.13/mo

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5-yr fixed avg.

Principal: $1,826,880Interest: $1,203,460
Mortgage Amount$1,826,880
Total Interest$1,203,460
Est. Property Tax$1,618/mo
Total Cost$3,030,340

Rates shown are estimates based on typical Ontario 5-year fixed rates. Canadian mortgages use semi-annual compounding as required by law. CMHC insurance applies to purchases under $1.5M with less than 20% down. Estimated property tax uses an approximate 0.85% rate. Contact us for current rate options and pre-approval.

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Neighbourhood Guide: Yonge-St. Clair

Discover Yonge-St. Clair

Yonge-St. Clair is a vibrant community in the Greater Toronto Area, offering excellent amenities, schools, and transportation options. This area is popular with families and professionals seeking a balanced lifestyle with access to urban conveniences and natural spaces.

Why Live in Yonge-St. Clair

  • Convenient location in Annex / Yorkville / Summerhill
  • Access to local shops and dining
  • Good public transit connections
  • Community parks and green spaces
  • Well-maintained neighbourhoods

Nearby Schools

Local Elementary SchoolPublic Elementary
Local Secondary SchoolPublic High School

Transit & Commuting

  • MiWay bus routes throughout the area
  • GO Transit stations within driving distance
  • Easy highway access to 401/403/QEW
  • Walking distance to local amenities

Parks & Amenities

  • Local parks and recreational facilities
  • Community centres
  • Shopping plazas nearby
  • Restaurants and cafes

Lifestyle & Community

Yonge-St. Clair offers a wonderful quality of life with a mix of residential charm and urban convenience. Residents enjoy easy access to schools, parks, and shopping, making it an ideal location for families and professionals alike.

70
Walk Score
Varies
Price Range

29 Highbourne Avenue, Annex / Yorkville / Summerhill

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Investor Analysis

Rental income estimator & ROI calculator

Estimated Monthly Rent
$3,200/mo
Range: $2,720 - $3,680
Cap Rate (ROI)
0.6%
Below Average

Monthly Cash Flow Breakdown

Rental Income+$3,200
Maintenance Fees-$0
Property Tax (est.)-$1,618
Insurance (est.)-$476
Net Cash Flow+$1,106

Note: These are estimates only. Actual figures may vary based on market conditions, property condition, and other factors. Consult with a financial advisor for personalized advice.

Joe Battaglia - Top Real Estate Agent in Mississauga, REMAX Realty Specialists

Joe's Thoughts

Honest perspective from 30+ years of GTA real estate experience

Premium Pricing

At $2076/sqft, this property is priced above the Yorkville average of $950/sqft. I'd want to see upgraded finishes, premium location, or recent renovations to justify this price point. During our showing, I'll point out exactly what you're paying extra for.

Detached Home Advantages

Detached homes in Yorkville are increasingly scarce and valuable. You'll have no shared walls, full control over renovations, and typically stronger appreciation. Consider the lot size and potential for future additions or basement apartment income. Detached homes also offer the most flexibility for growing families.

Family-Friendly Layout

4 bedrooms hits the sweet spot for most families. You'll have room for 2-3 children plus a home office or guest room. This is the most sought-after configuration for families relocating to Yorkville. Good resale value as demand remains consistent.

Bathroom Count Matters

With 3 bathrooms, morning routines are much smoother. Multiple bathrooms significantly improve daily livability and are a major selling point for resale. Buyers consistently pay more for adequate bathroom counts - this is a strong feature.

About Yonge-St. Clair

I know Yonge-St. Clair well from working with many buyers and sellers here. Each pocket has its own character - let me share what I've learned about this specific street and block. During our showing, I'll point out local amenities, school catchments, and what similar homes have sold for recently.

Investment Perspective

Looking at this as an investment: Yorkville properties have averaged 5-7% annual appreciation over the past decade. Your estimated monthly carrying costs would be around $9,515 (mortgage, taxes, insurance). Consider whether you're comfortable with this as both a home and a financial commitment.

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    29 Highbourne Avenue | $2,283,600 | Battaglia Team