305 Winona Drive, Toronto C03

Price: $1,289,000

4 bedrooms, 3 bathrooms

1,100 - 1,499 sqft

Property Type: Semi-Detached

MLS#: C13696966

Grow in one of Toronto's most walkable, family loved pockets. Fully renovated to the studs with permits in 2015, this home offers an open concept main floor built for everyday family life: cook, play and keep an eye on the kids. The versatile sunroom can be a playroom or a home office. Upstairs, three generous bedrooms, modern bathroom and a large balcony are located. Overlooking the backyard, the balcony is a peaceful retreat for morning coffee. The lower level has its own walkout entrance, 7ft ceiling, and separate hydro meter ideal as a nanny suite, in-law space, or income unit to help offset the mortgage as your family settles in. Tucked between Wychwood Barns and the shops and patios of Corso Italia, you're steps from parks, cafes, and everyday errands, the kind of neighbourhood where kids grow up knowing their block. This is a home your family can plant down roots and grow with for years to come.

305 Winona Drive - Semi-Detached photo 1 of 30 in Forest Hill / Deer Park, Ontario
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New Listing
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$1,289,000 - 305 Winona Drive, Forest Hill

Semi-Detached for Sale in Forest Hill

New — Listed 3 days ago

Neighbourhood: Oakwood Village

4Beds
3Baths
1,100 - 1,499Sq Ft
Semi-Detached
Property Details
MLS Number
C13696966
Property Type
Semi-Detached
Status
active
Days on Site
3
Bedrooms
4
Bathrooms
3
Square Feet
1,100 - 1,499 sqft
Neighbourhood
Forest Hill / Deer Park
Listing Brokerage
RE/MAX ULTIMATE REALTY INC.
Description

Grow in one of Toronto's most walkable, family loved pockets. Fully renovated to the studs with permits in 2015, this home offers an open concept main floor built for everyday family life: cook, play and keep an eye on the kids. The versatile sunroom can be a playroom or a home office. Upstairs, three generous bedrooms, modern bathroom and a large balcony are located. Overlooking the backyard, the balcony is a peaceful retreat for morning coffee. The lower level has its own walkout entrance, 7ft ceiling, and separate hydro meter ideal as a nanny suite, in-law space, or income unit to help offset the mortgage as your family settles in. Tucked between Wychwood Barns and the shops and patios of Corso Italia, you're steps from parks, cafes, and everyday errands, the kind of neighbourhood where kids grow up knowing their block. This is a home your family can plant down roots and grow with for years to come.

Mortgage Calculator

Estimate your monthly payments for this property

Estimated Payment

$5,701.68/mo

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5-yr fixed avg.

Principal: $1,031,200Interest: $679,305
Mortgage Amount$1,031,200
Total Interest$679,305
Est. Property Tax$913/mo
Total Cost$1,710,505

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: Oakwood Village

Discover Oakwood Village

Oakwood Village 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 Oakwood Village

  • Convenient location in Forest Hill / Deer Park
  • 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

Oakwood Village 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

305 Winona Drive, Forest Hill / Deer Park

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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)
1.9%
Below Average

Monthly Cash Flow Breakdown

Rental Income+$3,200
Maintenance Fees-$0
Property Tax (est.)-$913
Insurance (est.)-$269
Net Cash Flow+$2,018

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 $1172/sqft, this property is priced above the Forest Hill 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.

Just Listed - Act Strategically

This property hit the market within the last week. In Forest Hill's current market, desirable homes often receive multiple offers within 5-7 days. If you're seriously interested, I recommend booking a showing immediately. However, never let urgency override due diligence - we'll still do proper inspections.

Detached Home Advantages

Detached homes in Forest Hill 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 Forest Hill. 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 Oakwood Village

I know Oakwood Village 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.

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    305 Winona Drive | $1,289,000 | Battaglia Team