Single Family Homes in Winston, OR

24 for sale · 41 homes listed · Updated November 9, 2026

• 411 Woodland Drive, Winston 97496 $669,000 · 4 bd · 2 ba · 2,240 sqft
• 6700 Upper Olalla Road, Winston 97496 $1,050,000 · 3 bd · 3 ba · 2,720 sqft
• 380 Northwest Cary Street, Winston 97496 $350,000 · 4 bd · 2 ba · 1,710 sqft
• 1349 Willis Creek Road, Winston 97496 $1,099,900 · 3 bd · 3 ba · 2,856 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
• 128 Watusi Court, Winston 97496 $430,000 · 3 bd · 2 ba · 1,832 sqft
• 351 Southeast Darrell Avenue, Winston 97496 $309,900 · 3 bd · 1 ba · 960 sqft
• 623 Southeast Garden Way Drive, Winston 97496 $409,900 · 3 bd · 2 ba · 1,680 sqft
• 161 Collins Court, Winston 97496 $469,900 · 3 bd · 2 ba · 1,770 sqft
• 158 Collins Court, Winston 97496 $439,900 · 3 bd · 2 ba · 1,564 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
• 591 Northwest Douglas Boulevard, Winston 97496 $979,500 · 3 bd · 2 ba · 1,526 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
• 756 Southeast Hall Street, Winston 97496 $449,000 · 3 bd · 2 ba · 1,512 sqft
• 740 Southeast Hall Street, Winston 97496 $459,900 · 3 bd · 2 ba · 1,580 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
• 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
• 630 Southeast Rose Ridge Drive, Winston 97496 $409,900 · 3 bd · 2 ba · 1,580 sqft
• 78 Southeast Darrell, Winston 97496 $310,000 · 3 bd · 3 ba · 1,355 sqft
• 66 Northwest Cary Street, Winston 97496 Pending $245,000 · 2 bd · 1 ba · 1,224 sqft
• 260 Southeast Logan Street, Winston 97496 Pending $439,900 · 3 bd · 2 ba · 1,629 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
• 265 Southeast Logan Street, Winston 97496 Pending $409,900 · 3 bd · 2 ba · 1,555 sqft
• 150 Southwest Brantley Drive, Winston 97496 Pending $369,000 · 4 bd · 3 ba · 2,270 sqft
• 330 Wil Way, Winston 97496 Pending $509,999 · 4 bd · 2 ba · 2,091 sqft
• 509 Northwest Elwood Drive, Winston 97496 Pending $259,000 · 3 bd · 1 ba · 960 sqft
• 600 Southeast Parkway Drive, Winston 97496 Pending $409,000 · 3 bd · 3 ba · 1,761 sqft
• 2620 Northwest Brockway Road, Winston 97496 Pending $469,900 · 3 bd · 2 ba · 4,024 sqft
• 340 Northwest Elizabeth Avenue, Winston 97496 Pending $305,000 · 3 bd · 2 ba · 1,594 sqft
• 535 Southeast Parkway Drive, Winston 97496 Pending $439,900 · 3 bd · 2 ba · 1,442 sqft
• 1090 East Willis Creek Road, Winston 97496 Pending $399,000 · 3 bd · 2 ba · 2,167 sqft
• 61 Southwest Oak Street, Winston 97496 Pending $420,000 · 2 bd · 2 ba · 1,294 sqft
• 754 Southeast Hall Street, Winston 97496 Pending $379,900 · 3 bd · 2 ba · 1,245 sqft
• 635 Wil Way, Winston 97496 Active Under Contract $619,900 · 4 bd · 4 ba · 3,072 sqft
• 375 Porter Creek Road, Winston 97496 Sold on Sep 22, 2026 $775,000 · 4 bd · 5 ba · 3,000 sqft