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Copyright © 2026 The Canadian Home Realty Inc.
  • Ontario
  • Oakville
  • 1019 - WM Westmount
  • 2099 Helmsley Avenue
2099-helmsley-avenue-oakville-ontario-w12810144
2099-helmsley-avenue-oakville-ontario-w12810144
2099-helmsley-avenue-oakville-ontario-w12810144
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  • Sold Sold in Mar 2026
  • Detached

2099 Helmsley Avenue

Oakville, 1019 - WM Westmount
  • 4 + 1 Bedrooms
  • 4 Bathrooms
  • 2 Garage
  • Share
Sold Price: $ 2,400,000
2.04%
Listed Price: $ 2,450,000
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Key Facts About 2099 Helmsley Avenue, Oakville

  • Tax $9,782 / 2025
  • Property Type Residential
  • Building Type Detached
  • Building Style 2-Storey
  • Building Age 16-30
  • Size 3000 - 3500 feet²
  • Lot Irregularities Large Pie Lot
  • Lot Size 35.27 x 140.35 feet
  • Parking 2 garage, 3 parking
  • Basement Finished
  • Listing # W12810144
  • Data Source PROPTX
  • Days on Market 24
  • Listed On 22/02/2026
  • Updated On 23/03/2026
  • Market Demand
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Description

Your Private Summer Oasis in Westmount! Stop scrolling! 2099 Helmsley Ave has officially hit the market, and it's the definition of "turn-key." This isn't just a house; it's a 3,300+ sq. ft. lifestyle upgrade in one of Oakville's most coveted pockets. Why you'll fall in love: Fully Renovated: Brand-new kitchen and spa-like baths. No carpet on the main or upper floors-just sleek, clean lines. Room for Everyone: 4+1 Bedrooms plus a separate office on the main floor, 4 Baths, and a massive finished basement for gym/office/play. The Backyard (The R

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Property Details of 2099 Helmsley Avenue, Oakville

Property

  • Property Type Detached
  • Style 2-Storey
  • Fronting On E
  • Community 1019 - WM Westmount
  • Municipality Oakville

Inside

  • Bedrooms 4
  • Bathrooms 4
  • Bathroom Details 1, 2pc Main
  • Bathroom Details 1, 3pc Basement
  • Bathroom Details 1, 4pc Second
  • Bathroom Details 1, 5pc Second
  • Basement Finished
  • Kitchen 1
  • Rooms 10
  • Family Rooms Y
  • Central Vac N
  • Fireplace Y

Utilities

  • Water Municipal
  • Cooling Central Air
  • Heating Type Forced Air
  • Heating Fuel Gas
    • Cable Y
    • Gas Y
    • Telephone Y
    • Electricity Y

Building

  • Size 3000 - 3500 feet²
  • Architecture Style 2-Storey
  • Exterior Feature Brick
  • Pool Inground
  • Building Age 16-30

Parking

  • Drive Way Private Double
  • Garage Type Built-In
  • Garage 2
  • Parking Places 3
  • Total Parking Places 5

Land

  • Sewer Sewer
  • Frontage 35.27
  • Depth 140.35
  • Zoning RL6
  • Lot Size 35.27 x 140.35 feet
  • Lot Size Code Feet
  • Cross Street Upper Middle & Bronte

Features

  • Fenced Yard Y
  • Golf Y
  • Hospital Y
  • Marina Y
  • Public Transit Y

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Our Estimate

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Estimated Rent

$ 5,822

Rental Yield

2.47%

School Score

8.8/10

Rental Score

0.5/5

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Rooms

Bathroom (2 pcs)
Level: Main
Bathroom (3 pcs)
Level: Basement
Bathroom (4 pcs)
Level: Second
Bathroom (5 pcs)
Level: Second

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Expense Breakdown

Monthly Mortgage Payment

$0/monthly

30 Year , 3.99% interest

Cash Expenditure for Home Purchase

$1,000

  • Downpayment
    $0
  • PST on Mortgage Insurance
    $0
  • Land Transfer Tax
    $0
  • Lawyer Fees
    $1,000
  • Title Insurance
    $0

Monthly Expenses After Home Purchase

$569

  • Mortgage Payment
    $0
  • Property Insurance
    $50
  • Property Tax
    $250
  • Phone
    $40
  • Monthly debt payments
    $0
  • Cable
    $60
  • Utilities
    $124
  • Internet
    $45
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Copyright:© The Canadian Home Realty Inc. All rights reserved. The Canadian Home Realty Inc is a registered real estate brokerage.

About 2099 Helmsley Avenue, Oakville

Welcome to your private summer oasis in Westmount! This stunning house for sale in Oakville , located at 2099 Helmsley Avenue, Oakville, is an exceptional opportunity for those seeking a spacious and beautifully renovated home. With over 3,300 square feet of living space, this detached two-storey brick residence is perfect for families or anyone looking to upgrade their lifestyle in one of Oakville's most sought-after communities.

As you approach 2099 Helmsley Avenue, Oakville, you will be greeted by an extended private double driveway that leads to a built-in garage, providing ample parking for up to three vehicles. The exterior of the house is not only attractive but also meticulously maintained, showcasing the pride of ownership that is evident throughout the property.

Step inside this house for sale in Oakville, and you will immediately appreciate the modern finishes and thoughtful design. The main floor boasts a spacious family room, perfect for entertaining or relaxing with loved ones. The heart of the home is undoubtedly the brand-new kitchen, which has been fully renovated to meet the needs of any aspiring chef. With sleek, clean lines and high-quality appliances, this kitchen is both functional and stylish.

This house features a total of four bedrooms, providing ample space for everyone. In addition to the bedrooms, there is a separate den on the main floor, which can be used as a home office or study, making it ideal for those who work from home. With four bathrooms, including spa-like facilities, there will never be a shortage of space for everyone to get ready in the morning.

One of the standout features of this property is the massive finished basement, which offers endless possibilities. Whether you envision a gym, office, or play area, this space is versatile and ready to be tailored to your needs. The total number of rooms in this house for sale in Oakville is ten, ensuring that there is room for everyone to enjoy their own space.

The backyard is truly the real MVP of this home. Set on a generous 35 x 140 feet lot, the outdoor space is sun-drenched and perfect for summer gatherings. The inground pool is a fantastic feature for those hot summer days, while the gazebo provides a shaded retreat for relaxation. There is still plenty of grassy area for children or pets to run and play, making it an ideal setting for family fun and entertaining.

This house for sale in Oakville is not just about the home itself; it is also about the community. The property is located in a neighbourhood that boasts top-ranked schools, including Captain R. Wilson and Garth Webb, making it an excellent choice for families. Additionally, you will find that the Oakville Trafalgar Memorial Hospital, various shops, and Oakville Transit are all just minutes away, ensuring convenience in your daily life. Access to Highway 407 and the QEW is also within easy reach, making commuting a breeze.

With central air conditioning and forced air heating, this home ensures comfort throughout the year. The property is connected to municipal water and sewer systems, providing peace of mind. Although there is no central vacuum system, the unfurnished nature of the home allows you to personalise the space to your liking.

In summary, 2099 Helmsley Avenue, Oakville, is a remarkable house for sale in Oakville that combines modern living with a fantastic outdoor space. With its extensive renovations, spacious layout, and desirable location, this property is a must-see for anyone looking to make a lifestyle upgrade. Don't miss your chance to own this exceptional home in a vibrant community.

WM Westmount is a charming residential area located in the picturesque town of Oakville, Ontario. This community is characterised by its tree-lined streets, well-maintained parks, and a variety of family-friendly amenities, making it an ideal place for those seeking a tranquil yet vibrant environment. The neighbourhood boasts a mix of modern homes and established properties, providing a welcoming atmosphere for residents of all ages. With convenient access to local shops, schools, and recreational facilities, WM Westmount offers a perfect blend of suburban comfort and urban convenience, making it a delightful choice for prospective residents looking to settle in a thriving community.

Schools in the Neighbourhood

This property is ideally situated near several reputable schools, making it a great choice for families. The closest is Captain R. Wilson Public School, just 0.1 km away, which offers English-language education for grades JK to 8 and boasts a commendable school rating of 8.6. For secondary education, Garth Webb Secondary School is located 0.8 km from the property, providing a strong academic program for grades 9 to 12, with an impressive rating of 8.8. Additionally, St. Joan of Arc Catholic Elementary School is a mere 0.4 km away, offering a Catholic education in English for grades JK to 8, rated at 8.4. Other nearby options include Palermo Public School and St. Mary Catholic Elementary School, both within 1.4 km and 1.1 km, respectively, providing diverse educational experiences in both English and French. For secondary education, St. Ignatius of Loyola Catholic Secondary School is 2.8 km away, offering a solid program for grades 9 to 12. With a variety of schools catering to different educational preferences and languages, this location is perfect for families seeking quality education for their children.

FAQs About 2099 Helmsley Avenue, Oakville

How many bathrooms does this property have?

This property features 4 bathroom(s) and 4 bedroom(s).

Does this 4 bedroom property have additional bedrooms or a den?

This Detached property includes 1 additional bedrooms.

What is the square footage (sqft) of this Detached property?

The total square footage of this Detached 4 bed property in Oakville is 3000 - 3500.

How many parking spaces are available with this property?

2099 Helmsley Avenue boasts 3 convenient parking spaces.

How many cars can be parked in the garage of 2099 Helmsley Avenue?

This property features a garage with space for 2 cars.

What type of garage does this property have?

This property includes an Built-In garage with space for 2 cars.

Does this property have a basement?

Yes, this property has a basement.

What type of basement is it?

This property features Finished basement.

Does this property have a swimming pool?

Yes, this property has a Inground swimming pool.

Does this property have a fireplace?

A fireplace is available in this property.

How many kitchens does this property have?

This property includes 1 kitchen(s).

Is there a maintenance fee associated with this property?

Information about the maintenance fee is not available.

Is this property furnished?

Information about whether this property is furnished is not available.

What type of heating system is in place?

The heating system in place is a Forced Air.

What utilities are available for this property?

This property include following utilities : Cable, Gas, Telephone, Electricity.

School Rating for 2099 Helmsley Avenue, Oakville

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Listing History

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