2099 Helmsley Avenue

2099 Helmsley Avenue
2099 Helmsley Avenue
2099 Helmsley Avenue
+44
4+1
 bed
4
 bath
5
 parking
3000 - 3500
 sqft
Detached
$2,450,000
For Sale
9 hours
 on site
$2,450,000
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Size
-
Lot size
10193 sqft
Street frontage
-
Possession
Flexible
Price per sqft
$700 - $817
Taxes
$9,782 (2026)
Parking Type
-
Style
2-Storey
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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 Real MVP): A massive, sun-drenched lot with an in-ground pool, gazebo, and still tons of grass for the kids/pups to run. It is the spot for summer 2026. Meticulously Maintained: Extended driveway and oversized rooms that actually fit your furniture. The Neighborhood Perks: Top-ranked schools (Captain R. Wilson & Garth Webb) Minutes to the Oakville Trafalgar Memorial Hospital, Shops, Oakville Transit, and easy Hwy 407/QEW access are right around the corner.
Broker: Century 21 Miller Real Estate Ltd.
MLS®#: W12810144
Property details
Parking:
5
Parking type:
-
Property type:
Detached
Heating type:
Forced Air
Style:
2-Storey
MLS Size:
3000-3500 sqft
Lot front:
35 Ft
Lot depth:
140 Ft
Listed on:
Feb 22, 2026
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Instant estimate:
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$54,493
lower than listed price
i
High
$2,512,469
Mid
$2,395,507
Low
$2,289,960
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About 2099 Helmsley Avenue

2099 Helmsley Avenue is an Oakville detached house for sale. 2099 Helmsley Avenue has an asking price of $2450000, and has been on the market since February 2026. This detached house has 4+1 beds, 4 bathrooms and is 3000-3500 sqft. 2099 Helmsley Avenue resides in the Oakville West Oak Trails neighbourhood, and nearby areas include Palermo West, Glen Abbey, Bronte Creek and Orchard.

There are a lot of great restaurants around 2099 Helmsley Ave, Oakville. If you can't start your day without caffeine fear not, your nearby choices include Starbucks. For groceries there is The Gallant Baker which is only a 11 minute walk.

If you are looking for transit, don't fear, there is a Bus Stop (Westoak Trails Blvd / Grand Oak Trail) a 3-minute walk.