386 Winona Drive, Toronto C03

Price: $1,199,999

3 bedrooms, 3 bathrooms

1,100 - 1,499 sqft

Property Type: Detached

MLS#: C13698878

Welcome to your new home in the heart of Oakwood Village! Situated on one of the neighbourhood's most sought-after streets, Winona Drive, this extensively renovated home offers the perfect blend of style, comfort, and functionality. The main floor features gleaming hardwood floors, a bright open-concept kitchen designed for family meals and entertaining, and the added convenience of a rare main-floor powder room. Upstairs, you'll find three generously sized bedrooms and a beautifully updated bathroom. Step outside to your private backyard oasis - the perfect setting for summer BBQs, entertaining friends, or simply enjoying your own outdoor space. The finished basement with a separate entrance adds even more flexibility, offering endless possibilities for a family room, home gym, office, or in-law suite. Located just steps from St. Clair West, Wychwood Barns, Cedarvale Ravine, parks, transit, and some of Toronto's top schools, this is a fantastic opportunity to own a move-in-ready home in one of the city's most desirable neighbourhoods. A wonderful home in an exceptional location, this one truly checks all the boxes!

386 Winona Drive - Detached photo 1 of 38 in Forest Hill / Deer Park, Ontario
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New Listing
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$1,199,999 - 386 Winona Drive, Forest Hill

Detached for Sale in Forest Hill

New — Listed 3 days ago

Neighbourhood: Oakwood Village

3Beds
3Baths
1,100 - 1,499Sq Ft
Detached
Property Details
MLS Number
C13698878
Property Type
Detached
Status
active
Days on Site
3
Bedrooms
3
Bathrooms
3
Square Feet
1,100 - 1,499 sqft
Neighbourhood
Forest Hill / Deer Park
Listing Brokerage
RIGHT AT HOME REALTY
Description

Welcome to your new home in the heart of Oakwood Village! Situated on one of the neighbourhood's most sought-after streets, Winona Drive, this extensively renovated home offers the perfect blend of style, comfort, and functionality. The main floor features gleaming hardwood floors, a bright open-concept kitchen designed for family meals and entertaining, and the added convenience of a rare main-floor powder room. Upstairs, you'll find three generously sized bedrooms and a beautifully updated bathroom. Step outside to your private backyard oasis - the perfect setting for summer BBQs, entertaining friends, or simply enjoying your own outdoor space. The finished basement with a separate entrance adds even more flexibility, offering endless possibilities for a family room, home gym, office, or in-law suite. Located just steps from St. Clair West, Wychwood Barns, Cedarvale Ravine, parks, transit, and some of Toronto's top schools, this is a fantastic opportunity to own a move-in-ready home in one of the city's most desirable neighbourhoods. A wonderful home in an exceptional location, this one truly checks all the boxes!

Mortgage Calculator

Estimate your monthly payments for this property

Estimated Payment

$5,308.00/mo

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5-yr fixed avg.

Principal: $959,999Interest: $632,401
Mortgage Amount$959,999
Total Interest$632,401
Est. Property Tax$850/mo
Total Cost$1,592,400

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

386 Winona Drive, Forest Hill / Deer Park

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Investor Analysis

Rental income estimator & ROI calculator

Estimated Monthly Rent
$2,800/mo
Range: $2,380 - $3,220
Cap Rate (ROI)
1.7%
Below Average

Monthly Cash Flow Breakdown

Rental Income+$2,800
Maintenance Fees-$0
Property Tax (est.)-$850
Insurance (est.)-$250
Net Cash Flow+$1,700

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

Fair Market Value

At $1091/sqft, this property is priced in line with current Forest Hill market conditions. The pricing suggests the seller has done their homework. We may have modest room for negotiation, typically 2-4% in today's market.

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.

Starter Home Potential

3 bedrooms works well for couples planning families or small families with one child. Consider whether you might outgrow the space in 5-7 years. If so, factor in potential moving costs when making your decision. Alternatively, some buyers convert a bedroom to an office and make it work long-term.

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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    386 Winona Drive | $1,199,999 | Battaglia Team