Homes under $400K in Winston, OR

14 for sale · 24 homes listed · Updated November 9, 2026

380 Northwest Cary Street, Winston 97496 $350,000 · 4 bd · 2 ba · 1,710 sqft
340 Southeast Darrell Avenue, Winston 97496 $270,000 · 3 bd · 1 ba · 1,000 sqft
3707 Willis Creek Road, Winston 97496 $250,000 · 2 bd · 1 ba · 1,070 sqft
351 Southeast Darrell Avenue, Winston 97496 $309,900 · 3 bd · 1 ba · 960 sqft
76 Southeast Darrell Avenue, Winston 97496 $299,000 · 3 bd · 2 ba · 1,318 sqft
411 Sunnyside Drive, Winston 97496 $340,000 · 3 bd · 2 ba · 1,559 sqft
2461 Northwest Brockway Road, Winston 97496 $399,900 · 3 bd · 2 ba · 1,296 sqft
750 Southeast Tokay Street, Winston 97496 $329,900 · 3 bd · 2 ba · 1,250 sqft
669 Northwest T Street, Winston 97496 $369,500 · 3 bd · 2 ba · 1,416 sqft
410 Northwest Elizabeth Avenue, Winston 97496 $269,900 · 3 bd · 2 ba · 1,066 sqft
271 Southeast Robinson Street, Winston 97496 $300,000 · 3 bd · 2 ba · 1,296 sqft
185 Southeast Lebleu Lane, Winston 97496 $329,900 · 3 bd · 2 ba · 1,257 sqft
11 Northeast Brosi Orchard Road, Winston 97496 $375,000 · 3 bd · 3 ba · 2,610 sqft
78 Southeast Darrell, Winston 97496 $310,000 · 3 bd · 3 ba · 1,355 sqft
1580 Winston Section Road, Winston 97496 Pending $174,000 · 3 bd · 2 ba · 1,188 sqft
66 Northwest Cary Street, Winston 97496 Pending $245,000 · 2 bd · 1 ba · 1,224 sqft
71 Southeast Ronald Street, Winston 97496 Pending $249,000 · 2 bd · 1 ba · 939 sqft
0 Rice Creek Road, Winston 97496 Pending $190,000 · 1 bd · 1 ba · 1,000 sqft
150 Southwest Brantley Drive, Winston 97496 Pending $369,000 · 4 bd · 3 ba · 2,270 sqft
600 Southeast Edgewood Street, Winston 97496 Pending $169,900 · 2 bd · 1 ba · 800 sqft
509 Northwest Elwood Drive, Winston 97496 Pending $259,000 · 3 bd · 1 ba · 960 sqft
340 Northwest Elizabeth Avenue, Winston 97496 Pending $305,000 · 3 bd · 2 ba · 1,594 sqft
1090 East Willis Creek Road, Winston 97496 Pending $399,000 · 3 bd · 2 ba · 2,167 sqft
754 Southeast Hall Street, Winston 97496 Pending $379,900 · 3 bd · 2 ba · 1,245 sqft