Homes for Sale in Winston Park, Oakville

4
For sale now
$3,900,000
Median asking price
$750,000 to $17,650,000
Stop anytime.

Newest homes in Winston Park, Oakville

Page 1 of 1 · 4 for sale · newest first

2078 Upper Middle Road E
For Sale
$3,900,000
2078 Upper Middle Road E, Oakville
· MLS® W13626156
2078 Upper Middle Road E
For Sale
$3,900,000
2078 Upper Middle Road E, Oakville
· MLS® W13626230
2300 Winston Park Drive
For Sale
$17,650,000
2300 Winston Park Drive, Oakville
· MLS® W13565890
2578 Bristol Circle
For Sale
$750,000
2578 Bristol Circle, Oakville
· MLS® W12834600
Page 1 of 1

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Communities
Bronte (91) Bronte Creek (30) Central (58) Clearview (13) College Park (34) Falgarwood (23) Ford (34) Glen Abbey (76) Glenorchy (110) Joshua Creek (29) Joshua Meadows (65) Morrison (57) Northwest (12) Old Oakville (54) Queen Elizabeth (61) River Oaks (84) Rural Oakville (10) Southwest (37) Wedgewood Creek (23) West (101) West Oak Trails (23) Westmount (74) Winston Park (4)
Popular searches
New construction (1) 3,000+ sq ft (3) Vacant (3) 60+ days on market (4) Under $750K (1) Under $1M (1) Luxury ($2M+) (3)
Price ranges
$700,000 to $800,000 $800,000 to $900,000 $900,000 to $1,000,000 Over $1,000,000

As of November 1, 2026, there are 4 homes for sale in Winston Park, Oakville, with a median asking price of $3,900,000 (from $750,000 to $17,650,000).

Price mix

$700K–$800K1
$800K–$900K0
$900K–$1,000K0
$1,000K+3

Nearby communities

Glenorchy110 listings · median $1,048,950 West101 listings · median $1,999,900 Bronte91 listings · median $1,469,900 River Oaks84 listings · median $949,388 Glen Abbey76 listings · median $1,324,450 Westmount74 listings · median $839,500 Joshua Meadows65 listings · median $799,900 Queen Elizabeth61 listings · median $940,000

Questions, answered

How many homes are for sale in Winston Park, Oakville?

4 as of November 1, 2026.

What is the median asking price for homes in Winston Park, Oakville?

$3,900,000, with listings from $750,000 to $17,650,000.

Copyright 2026 All rights reserved. Toronto Regional Real Estate Board (TRREB) assumes no responsibility for the accuracy of any information shown. The information provided herein must only be used by consumers that have a bona fide interest in the purchase, sale or lease of real estate and may not be used for any commercial purpose or any other purpose.
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