Southwest Oakville homes for sale & real estate

38 homes

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NEW 8 HRS AGO

ABOUT THIS HOME
Southwest Oakville Homes for Sale
Welcome to 1194 Stirling Drive—an exceptional value and rare opportunity to own a substantial 4,294 sq. ft. home on an expansive private corner lot in one of SW Oakville’s most desirable neighbourhoods. The impressive scale, space and setting of this property truly must be experienced in person. Offering remarkable indoor and outdoor living, this home provides an incredible setting for family life, entertaining and enjoyment through every season. The spectacular backyard retreat features a newly built (2023) Gib-San Gunite pool, professionally landscaped grounds, a sprawling 1,500 sq. ft. deck and powered pergola, creating a private oasis and seamless extension of the home. Insi

$2,999,000

4 beds3.5 baths4,294 sq ft

1194 STIRLING Dr, Oakville, ON L6L 1E6

Sprawling deck • Powered pergola • Gib-san gunite pool

Listing provided by CREA

OPEN SAT, 2PM TO 4PM

ABOUT THIS HOME
Southwest Oakville Homes for Sale
Steps from the shoreline of Lake Ontario and Coronation Park. One of only seven homes on this secluded street, properties in this tightly held pocket rarely come to market. Occupying an oversized lot of more than 10,000 sq ft with nearly 90 ft of frontage (RL2-0 zoning), this fully renovated bungalow offers an exceptional combination of immediate enjoyment and long-term potential. The main level has been completely transformed with an open-concept layout featuring wide-plank hardwood flooring, custom millwork, crown moulding and pot lighting throughout. The kitchen anchors the space with HanStone quartz countertops, updated cabinetry, new hardware and backsplash, along with a full suite of

$1,789,900

3 beds2 baths— sq ft

1491 Trenton Rd, Oakville, ON L6L 1K9

Secluded street • Custom millwork • Oversized lot

NEW 22 HRS AGO

ABOUT THIS HOME
Southwest Oakville Homes for Sale
Welcome to 1399 Willowdown Road, an exceptional custom residence inspired by Frank Lloyd Wright's iconic Prairie designs, nestled on a spectacular ravine lot with a picturesque creek in prestigious South Oakville. Offering over 6,800 sq. ft. of beautifully finished living space, this remarkable home features 5 bedrooms upstairs plus 2 additional bedrooms in the finished lower level. The main floor impresses with soaring 10' ceilings, wide-plank oak flooring, custom millwork and an open-concept layout. At its heart is a chef-inspired kitchen with an oversized island, quartz counters, JennAir Professional Series appliances, extensive cabinetry and a butler pantry, opening to the expansive gre

$4,248,000

7 beds7 baths— sq ft

1399 Willowdown Rd, Oakville, ON L6L 1X2

Home theatre • Picturesque creek • Covered lanai

VIDEO TOUR

ABOUT THIS HOME
Southwest Oakville Homes for Sale
Straight from the pages of a design magazine, this beautifully renovated, on-trend home offers more than 4,500 sq. ft. of thoughtfully designed living space. Tucked away on a quiet cul-de-sac in prestigious Southwest Oakville, it's just steps from Appleby College and the shores of Lake Ontario. The property is professionally landscaped by award-winning Gildermans, creating a stunning setting that perfectly complements this exceptional home. Designed for both everyday living and effortless entertaining, the main floor features a spacious formal dining room and a warm, inviting family room with a wood-burning fireplace. The stunning chef's kitchen is a true showpiece, featuring a Wolf inducti

$2,999,000

4 beds6 baths— sq ft

105 Whittington Pl, Oakville, ON L6K 3W1

Chef's kitchen • 0.25 acre lot • Garage

VIDEO TOUR

ABOUT THIS HOME
Southwest Oakville Homes for Sale
Located in coveted West Harbour, come discover tranquility and elegance at 235 Lakewood Drive. Nestled on a generous . 56-acre lot, embraced by majestic foliage in a private cul-de-sac, this residence epitomizes serene living mere steps from the lake. Crafted by renowned architect Gren Weis, the fusion of stone and wood siding spans over 6,200 square feet. Step into the foyer with its soaring cathedral ceilings, offering glimpses of the expansive living spaces beyond. Designed for seamless flow, this sophisticated layout effortlessly accommodates both grand and intimate gatherings. A bespoke oak staircase adorned with shimmering Schonbek chandeliers leads to the upper levels, where solid oa

$4,390,000

5 beds5 baths— sq ft

235 Lakewood Dr, Oakville, ON L6K 1B3

Generous lot • Custom fireplace • Exquisite millwork

ABOUT THIS HOME
Southwest Oakville Homes for Sale
Welcome To Your Signature Address in Prestigious South Oakville. An exceptional opportunity to own a charming residence on a rare premium 75 x 150 ft lot, nestled in one of South West Oakville's most sought-after enclaves, surrounded by luxury custom homes. Ideally located within walking distance to the lake and top-ranked schools, this home offers the perfect blend of lifestyle, location, and future potentials.

$1,699,000

6 beds2 baths— sq ft

1350 Rebecca St, Oakville, ON L6L 1Z4

Top-ranked schools • 0.26 acre lot • Garage

Property at 1387 Willowdown Rd, Oakville, ON L6L 1X2, 4 beds, 4 baths

$2,849,000

4 beds4 baths— sq ft

1387 Willowdown Rd, Oakville, ON L6L 1X2

Property at 56 Birch Hill Lane, Oakville, ON L6K 2N9, 5 beds, 5 baths

$3,999,000

5 beds5 baths— sq ft

56 Birch Hill Lane, Oakville, ON L6K 2N9

Property at 224 Valleyview Crt, Oakville, ON L6L 5H8, 6 beds, 4 baths

$2,180,000

6 beds4 baths— sq ft

224 Valleyview Crt, Oakville, ON L6L 5H8

Property at 1566 Venetia Dr, Oakville, ON L6L 1K7, 3 beds, 2 baths

$1,778,000

3 beds2 baths— sq ft

1566 Venetia Dr, Oakville, ON L6L 1K7

Property at 70 Shorewood Pl, Oakville, ON L6K 3Y4, 4 beds, 6 baths

$5,250,000

4 beds6 baths— sq ft

70 Shorewood Pl, Oakville, ON L6K 3Y4

Property at 456 Lakeshore Rd W, Oakville, ON L6K 1G5, 5 beds, 7 baths

$4,898,000

5 beds7 baths— sq ft

456 Lakeshore Rd W, Oakville, ON L6K 1G5

Property at 150 Wolfdale Ave, Oakville, ON L6L 4S1, 5 beds, 7 baths

$4,999,369

5 beds7 baths— sq ft

150 Wolfdale Ave, Oakville, ON L6L 4S1

Property at 1358 Sedgewick Cres, Oakville, ON L6L 1X8, 3 beds, 1 bath

$1,600,000

3 beds1 bath— sq ft

1358 Sedgewick Cres, Oakville, ON L6L 1X8

Property at 1551 Warland Rd, Oakville, ON L6L 1N4, 4 beds, 5 baths

$3,498,000

4 beds5 baths— sq ft

1551 Warland Rd, Oakville, ON L6L 1N4

Property at 1392 Rebecca St, Oakville, ON L6L 1Z5, 3 beds, 2 baths

$1,795,000

3 beds2 baths— sq ft

1392 Rebecca St, Oakville, ON L6L 1Z5

Property at 104 Whittington Pl, Oakville, ON L6K 3V9, 5 beds, 4 baths

$2,599,999

5 beds4 baths— sq ft

104 Whittington Pl, Oakville, ON L6K 3V9

Property at 45 Shorewood Pl, Oakville, ON L6K 3Y3, 4 beds, 5 baths

$4,895,000

4 beds5 baths— sq ft

45 Shorewood Pl, Oakville, ON L6K 3Y3

Property at 225 Prince George Cres, Oakville, ON L6L 6P2, 5 beds, 7 baths

$3,789,988

5 beds7 baths— sq ft

225 Prince George Cres, Oakville, ON L6L 6P2

Property at 145 Wolfdale Ave, Oakville, ON L6L 4R9, 4 beds, 4 baths

$2,610,000

4 beds4 baths— sq ft

145 Wolfdale Ave, Oakville, ON L6L 4R9

Property at 84 Pebbleridge Pl, Oakville, ON L6K 3Y4, 7 beds, 9 baths

$7,499,999

7 beds9 baths— sq ft

84 Pebbleridge Pl, Oakville, ON L6K 3Y4

Property at 129 Wolfdale Ave, Oakville, ON L6L 4R9, 5 beds, 7 baths

$7,470,000

5 beds7 baths— sq ft

129 Wolfdale Ave, Oakville, ON L6L 4R9

Property at 89 Holyrood Ave, Oakville, ON L6K 2V4, 4 beds, 4 baths

$2,222,000

4 beds4 baths— sq ft

89 Holyrood Ave, Oakville, ON L6K 2V4

Property at 255 Spring Garden Rd, Oakville, ON L6L 5H5, 4 beds, 3 baths

$1,899,000

4 beds3 baths— sq ft

255 Spring Garden Rd, Oakville, ON L6L 5H5

Property at 168 Walby Dr, Oakville, ON L6L 4E2, 5 beds, 5 baths

$3,049,000

5 beds5 baths— sq ft

168 Walby Dr, Oakville, ON L6L 4E2

Property at 406 Christina Dr, Oakville, ON L6K 1H6, 4 beds, 4 baths

$2,380,000

4 beds4 baths— sq ft

406 Christina Dr, Oakville, ON L6K 1H6

Property at 1098 Lakeshore Rd W, Oakville, ON L6L 1E9, 5 beds, 5 baths

$4,650,000

5 beds5 baths— sq ft

1098 Lakeshore Rd W, Oakville, ON L6L 1E9

Property at 1601 Venetia Dr, Oakville, ON L6L 1K8, 7 beds, 5 baths

$3,188,000

7 beds5 baths— sq ft

1601 Venetia Dr, Oakville, ON L6L 1K8

Property at 125 Paliser Crt, Oakville, ON L6K 2H1, 5 beds, 5 baths

$2,797,000

5 beds5 baths— sq ft

125 Paliser Crt, Oakville, ON L6K 2H1

Property at 15 Lambert Common, Oakville, ON L6K 0H6, 6 beds, 8 baths

$7,900,000

6 beds8 baths— sq ft

15 Lambert Common, Oakville, ON L6K 0H6

Property at 183 Westminster Dr, Oakville, ON L6L 4H8, 3 beds, 3 baths

$1,899,900

3 beds3 baths— sq ft

183 Westminster Dr, Oakville, ON L6L 4H8

Property at 1373 Hixon St, Oakville, ON L6L 1R9, 3 beds, 2 baths

$1,775,000

3 beds2 baths— sq ft

1373 Hixon St, Oakville, ON L6L 1R9

Property at 370 Christina Dr, Oakville, ON L6K 1H6, 5 beds, 6 baths

$2,898,000

5 beds6 baths— sq ft

370 Christina Dr, Oakville, ON L6K 1H6

Property at 227 Sandwell Dr, Oakville, ON L6L 4P3, 3 beds, 2 baths

$1,649,999

3 beds2 baths— sq ft

227 Sandwell Dr, Oakville, ON L6L 4P3

Property at 1528 Warland Rd, Oakville, ON L6L 1N5, 3 beds, 2 baths

$1,899,000

3 beds2 baths— sq ft

1528 Warland Rd, Oakville, ON L6L 1N5

Property at 408 Lakeshore Rd W, Oakville, ON L6K 1G1, 6 beds, 8 baths

$4,295,000

6 beds8 baths— sq ft

408 Lakeshore Rd W, Oakville, ON L6K 1G1

Property at 489 Lakeshore Rd W, Oakville, ON L6K 1G4, 4 beds, 6 baths

$4,350,000

4 beds6 baths— sq ft

489 Lakeshore Rd W, Oakville, ON L6K 1G4

Property at 251 Third Line, Oakville, ON L6L 4A2, 4 beds, 2 baths

$1,499,000

4 beds2 baths— sq ft

251 Third Line, Oakville, ON L6L 4A2

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Average home prices near Southwest Oakville, ON

Neighborhoods

Old Oakville homes for sale
$3,199,000
College Park homes for sale
$1,213,500
Glen Abbey homes for sale
$1,208,944
West Oakville homes for sale
$1,999,000
Rural Oakville homes for sale
$994,500
Westmount homes for sale
$915,000
Central Oakville homes for sale
$1,286,940
Eastlake homes for sale
$3,499,999
River Oaks homes for sale
$964,450
Bronte homes for sale
$1,499,000

Southwest Oakville, ON real estate trends

$3.94M

Sale price

+97.1%
since last year

$1.06K

Sale $/sq ft

Under list price

Days on market

Down payment

—

Total homes sold

More to explore in Southwest Oakville, ON

How to buy a house in Southwest Oakville, ON

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Source: Statistics Canada, Census Divisions and Census Subdivisions, December 2018. Reproduced and distributed on an "as is" basis with the permission of Statistics Canada.

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