The 30 most popular homes for sale in Winchester
People love looking at homes—whether they're seriously searching for their next place or just daydreaming about what could be. Even though the current housing market is difficult, browsing is a well-established pastime and often on people's daily social media rotation.
To see which listings have caught the most attention lately, Redfin Real Estate analyzed the most-viewed homes for sale in the Winchester metro over the past 30 days. From fixer-uppers to move-in-ready dream homes, these listings had that "it" factor. Note: Listings were active on Redfin as of October 27, 2025; square footage was approximated.
#1. 3339 N Frederick, Pike Winchester, VA 22603
- Views: 1,375
- List price: $399,000
- Beds: 5 | Baths: 2 | Square feet: 3,378
- Price per square foot: $118.12
- See 3339 N Frederick, Pike Winchester, VA 22603 on Redfin.com
#2. 108 Comanche Trl, Winchester, VA 22602
- Views: 1,149
- List price: $189,900
- Beds: 3 | Baths: 1 | Square feet: 1,024
- Price per square foot: $185.45
- See 108 Comanche Trl, Winchester, VA 22602 on Redfin.com
#3. 699 Hoover Young Dr, Capon Bridge, WV 26711
- Views: 1,120
- List price: $195,000
- Beds: 2 | Baths: 1 | Square feet: 640
- Price per square foot: $304.69
- See 699 Hoover Young Dr, Capon Bridge, WV 26711 on Redfin.com
#4. 102 Conrad Ct, Winchester, VA 22603
- Views: 1,063
- List price: $89,900
- Beds: 3 | Baths: 2 | Square feet: 1,453
- Price per square foot: $61.87
- See 102 Conrad Ct, Winchester, VA 22603 on Redfin.com
#5. 129 E Cork St, Winchester, VA 22601
- Views: 1,007
- List price: $297,000
- Beds: 2 | Baths: 1.5 | Square feet: 935
- Price per square foot: $317.65
- See 129 E Cork St, Winchester, VA 22601 on Redfin.com
#6. 103 Eastern Cedar Ct, Paw Paw, WV 25434
- Views: 1,005
- List price: $335,000
- Beds: 3 | Baths: 2 | Square feet: 1,470
- Price per square foot: $227.89
- See 103 Eastern Cedar Ct, Paw Paw, WV 25434 on Redfin.com
#7. 70 Radnor Dr, Delray, WV 26714
- Views: 959
- List price: $265,000
- Beds: 2 | Baths: 2 | Square feet: 2,476
- Price per square foot: $107.03
- See 70 Radnor Dr, Delray, WV 26714 on Redfin.com
#8. 1251 Delray Rd, Augusta, WV 26704
- Views: 904
- List price: $309,000
- Beds: 2 | Baths: 2 | Square feet: 1,635
- Price per square foot: $188.99
- See 1251 Delray Rd, Augusta, WV 26704 on Redfin.com
#9. 103 Sharon Dr, Winchester, VA 22602
- Views: 895
- List price: $599,900
- Beds: 5 | Baths: 3 | Square feet: 4,047
- Price per square foot: $148.23
- See 103 Sharon Dr, Winchester, VA 22602 on Redfin.com
#10. 14 River Glen Rd, Paw Paw, WV 25434
- Views: 873
- List price: $299,500
- Beds: 4 | Baths: 2 | Square feet: 2,256
- Price per square foot: $132.76
- See 14 River Glen Rd, Paw Paw, WV 25434 on Redfin.com
#11. 212 NW Whitacre Rd, Gore, VA 22637
- Views: 763
- List price: $575,000
- Beds: 4 | Baths: 2.5 | Square feet: 2,184
- Price per square foot: $263.28
- See 212 NW Whitacre Rd, Gore, VA 22637 on Redfin.com
#12. 939 Woodland Ave, Winchester, VA 22601
- Views: 762
- List price: $279,900
- Beds: 2 | Baths: 2 | Square feet: 897
- Price per square foot: $312.04
- See 939 Woodland Ave, Winchester, VA 22601 on Redfin.com
#13. 0 Opossum Trl, Winchester, VA 22602
- Views: 755
- List price: $295,000
- Beds: 3 | Baths: 2 | Square feet: 1,300
- Price per square foot: $226.92
- See 0 Opossum Trl, Winchester, VA 22602 on Redfin.com
#14. 280 Graystone Ln, Winchester, VA 22603
- Views: 752
- List price: $830,000
- Beds: 5 | Baths: 5 | Square feet: 4,549
- Price per square foot: $182.46
- See 280 Graystone Ln, Winchester, VA 22603 on Redfin.com
#15. 175 Nixon Dr, Gore, VA 22637
- Views: 731
- List price: $409,900
- Beds: 3 | Baths: 2 | Square feet: 2,366
- Price per square foot: $173.25
- See 175 Nixon Dr, Gore, VA 22637 on Redfin.com
#16. 821 Apple Pie Ridge Rd, Winchester, VA 22603
- Views: 724
- List price: $1,999,999
- Beds: 5 | Baths: 5 | Square feet: 5,590
- Price per square foot: $357.78
- See 821 Apple Pie Ridge Rd, Winchester, VA 22603 on Redfin.com
#17. 514 Sleigh Dr, Cross Junction, VA 22625
- Views: 687
- List price: $590,000
- Beds: 4 | Baths: 2.5 | Square feet: 2,524
- Price per square foot: $233.76
- See 514 Sleigh Dr, Cross Junction, VA 22625 on Redfin.com
#18. 534 Grouse Dr, Winchester, VA 22602
- Views: 670
- List price: $330,000
- Beds: 3 | Baths: 3 | Square feet: 1,966
- Price per square foot: $167.85
- See 534 Grouse Dr, Winchester, VA 22602 on Redfin.com
#19. 301 Liberty Ave, Winchester, VA 22601
- Views: 653
- List price: $349,900
- Beds: 3 | Baths: 2 | Square feet: 1,293
- Price per square foot: $270.61
- See 301 Liberty Ave, Winchester, VA 22601 on Redfin.com
#20. 513 Van Fossen St, Winchester, VA 22601
- Views: 644
- List price: $360,000
- Beds: 4 | Baths: 2.5 | Square feet: 2,804
- Price per square foot: $128.39
- See 513 Van Fossen St, Winchester, VA 22601 on Redfin.com
#21. 100 Bubbling Spring Rd, Capon Bridge, WV 26711
- Views: 615
- List price: $79,995
- Beds: 2 | Baths: 1 | Square feet: 826
- Price per square foot: $96.85
- See 100 Bubbling Spring Rd, Capon Bridge, WV 26711 on Redfin.com
#22. 252 Punkin Ridge Dr, Clear Brook, VA 22624
- Views: 610
- List price: $725,000
- Beds: 4 | Baths: 3 | Square feet: 4,296
- Price per square foot: $168.76
- See 252 Punkin Ridge Dr, Clear Brook, VA 22624 on Redfin.com
#23. 1666 Apple Pie Ridge Rd, Winchester, VA 22603
- Views: 607
- List price: $309,900
- Beds: 2 | Baths: 1 | Square feet: 1,631
- Price per square foot: $190.01
- See 1666 Apple Pie Ridge Rd, Winchester, VA 22603 on Redfin.com
#24. 125 Whispering Knolls Dr, Winchester, VA 22603
- Views: 586
- List price: $245,000
- Beds: 3 | Baths: 2 | Square feet: not available
- Price per square foot: not available
- See 125 Whispering Knolls Dr, Winchester, VA 22603 on Redfin.com
#25. 580 N Braddock St, Winchester, VA 22601
- Views: 584
- List price: $425,000
- Beds: 4 | Baths: 2 | Square feet: 2,200
- Price per square foot: $193.18
- See 580 N Braddock St, Winchester, VA 22601 on Redfin.com
#26. 428 Westside Station Dr, Winchester, VA 22601
- Views: 584
- List price: $575,000
- Beds: 5 | Baths: 3.5 | Square feet: 4,235
- Price per square foot: $135.77
- See 428 Westside Station Dr, Winchester, VA 22601 on Redfin.com
#27. 707 E Cork St, Winchester, VA 22601
- Views: 583
- List price: $399,999
- Beds: 3 | Baths: 2.5 | Square feet: 1,680
- Price per square foot: $238.09
- See 707 E Cork St, Winchester, VA 22601 on Redfin.com
#28. 281 Light Rd, Winchester, VA 22603
- Views: 574
- List price: $609,900
- Beds: 3 | Baths: 2.5 | Square feet: 2,618
- Price per square foot: $232.96
- See 281 Light Rd, Winchester, VA 22603 on Redfin.com
#29. 562 Logger Dr, Gore, VA 22637
- Views: 565
- List price: $742,400
- Beds: 3 | Baths: 4 | Square feet: 4,088
- Price per square foot: $181.60
- See 562 Logger Dr, Gore, VA 22637 on Redfin.com
#30. 185 S Apple Ridge Rd, Romney, WV 26757
- Views: 550
- List price: $375,000
- Beds: 4 | Baths: 3 | Square feet: 3,640
- Price per square foot: $103.02
- See 185 S Apple Ridge Rd, Romney, WV 26757 on Redfin.com
