Southwest Oakville, Oakville

Southwest Oakville detached homes for sale

Every street in Southwest Oakville is detached, and the choice is between an original mid-century house, a renovated original and a new custom build. Originals span the 1950s to the 1970s, bungalows, split-levels and full two-storeys, often with single or double garages, hardwood under carpet, and lots deep enough for a pool and a large addition. Renovated originals typically have opened-up kitchens, second-storey additions and finished basements, and they are the value buy for families. Custom builds since the 2000s cluster near the water, around Coronation Park and Appleby College and on the cul-de-sacs off Lakeshore Road West, generally with three-car garages, walk-out basements and pools. For an original, check the roof, wiring, plumbing, insulation and whether the house ever had a septic system or oil tank, and ask for a survey and a review of the Town's tree by-law before planning a rebuild. For a new build, ask for the permits, the Tarion enrolment and the grading certificate.

Southwest Oakville detached homes by the numbers

Live from the MLS® feed · updated September 21, 2026

38 For sale now
18 New in 30 days
$2,899,000 Median asking price Middle half $1.8M to $4.4M
$1,144 Asking price per sq ft
32 days Median days listed
11% Listings with a price cut Median cut 4.8%

Newest Southwest Oakville detached homes for sale

See all 38 listings
111 Woodhaven Park Drive
111 Woodhaven Park Drive — photo 2
1 / 40
New
For Sale
$4,225,000
7 bd · 6 ba
111 Woodhaven Park Drive, Oakville
2 days on market
MLS® W13805920 · RE/MAX HALLMARK REALTY LTD.
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Questions people ask about Southwest Oakville

How wide are the lots in Southwest Oakville?

Most run sixty to eighty feet across and a good deal more than a hundred feet deep, with the lakeward streets and the courts off Lakeshore Road West stretching to a hundred feet or more. Streets near Rebecca Street have the narrower fifty-foot lots from the earliest subdivisions.

What should a buyer check on a 1960s side-split here?

Ask about the roof and windows, the furnace and air conditioning, any aluminum wiring, the state of the original galvanized or copper plumbing, and any history of water in the lower level, since some streets drain slowly in spring. Look for permits on additions and finished basements, and get a sewer scope on clay laterals.

Are garden suites or basement apartments permitted in Southwest Oakville?

Provincial rules now allow additional residential units on most urban lots, and the Town of Oakville's zoning allows basement apartments and, under set rules, detached garden suites, subject to setbacks, parking and servicing. The deep lots here suit them. Confirm the current by-law and permit requirements with the Town before relying on rental income.

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