Homes under $500K in Winston, OR

26 for sale · 41 homes listed · Updated September 25, 2026

• 1941 byron creek road, Winston 97496 $469,900 · 2 bd · 2 ba · 1,764 sqft
• 150 wil way, Winston 97496 $499,900 · 3 bd · 3 ba · 1,999 sqft
• 160 wil way, Winston 97496 $499,900 · 3 bd · 3 ba · 2,089 sqft
• 90 southeast darrell avenue, Winston 97496 $205,000 · 2 bd · 2 ba · 924 sqft
• 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
• 311 southeast grape avenue, Winston 97496 $459,000 · 3 bd · 1 ba · 1,250 sqft
• 186 woodduck street, Winston 97496 $366,000 · 3 bd · 2 ba · 1,613 sqft
• 572 dillard gardens road, Winston 97496 $498,000 · 2 bd · 2 ba · 1,440 sqft
• 2581 brockway road, Winston 97496 $499,900 · 3 bd · 3 ba · 2,576 sqft
• 3707 willis creek road, Winston 97496 $250,000 · 2 bd · 1 ba · 1,070 sqft
• 10 southwest peach lane, Winston 97496 $364,900 · 3 bd · 1 ba · 1,440 sqft
• 2620 northwest brockway road, Winston 97496 $469,900 · 3 bd · 2 ba · 4,024 sqft
• 185 southeast lebleu lane, Winston 97496 $329,900 · 3 bd · 2 ba · 1,257 sqft
• 675 southeast brush court, Winston 97496 $399,000 · 3 bd · 2 ba · 1,498 sqft
• 351 southeast darrell avenue, Winston 97496 $309,900 · 3 bd · 1 ba · 960 sqft
• 261 southeast darrell avenue, Winston 97496 $285,000 · 2 bd · 1 ba · 1,080 sqft
• 623 southeast garden way drive, Winston 97496 $409,900 · 3 bd · 2 ba · 1,680 sqft
• 104 kenya court, Winston 97496 $487,000 · 3 bd · 2 ba · 1,800 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 $319,000 · 3 bd · 2 ba · 1,318 sqft
• 411 sunnyside drive, Winston 97496 $364,000 · 3 bd · 2 ba · 1,559 sqft
• 70 northeast brosi orchard road, Winston 97496 $219,000 · 2 bd · 1 ba · 1,242 sqft
• 754 southeast hall street, Winston 97496 $379,900 · 3 bd · 2 ba · 1,245 sqft
• 2461 northwest brockway road, Winston 97496 $399,900 · 3 bd · 2 ba · 1,296 sqft
• 624 willis creek road, Winston 97496 Pending $495,000 · 3 bd · 2 ba · 1,782 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
• 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
• 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
• 600 southeast parkway drive, Winston 97496 Pending $409,000 · 3 bd · 3 ba · 1,761 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