Most expensive homes for sale in Winchester
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November 17, 2025
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Most expensive homes for sale in Winchester
Stacker compiled a list of the most expensive homes in Winchester listed for sale on realtor.com. Homes are ranked by price with ties broken by price per square foot.
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Where people in Winchester are looking to buy homes
#30. 111 Pawn Ct, Winchester
- Price: $699,999
- 5 bedrooms, 4 full bathrooms
- Square feet: 3,850
- Price per square foot: $181
- Days on market: 3 days (-$10,000 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms
- Square feet: 3,850
- Price per square foot: $181
- Days on market: 3 days (-$10,000 price reduction since listing)
- View listing on realtor.com
#29. 137 Stonebrook Rd, Winchester
- Price: $710,000
- 4 bedrooms, 4 full bathrooms
- Square feet: 3,783
- Price per square foot: $187
- Lot size: 1.0 acres
- Days on market: 59 days (-$39,900 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms
- Square feet: 3,783
- Price per square foot: $187
- Lot size: 1.0 acres
- Days on market: 59 days (-$39,900 price reduction since listing)
- View listing on realtor.com
#28. 191 Banks Dr, Winchester
- Price: $739,900
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,963
- Price per square foot: $186
- Lot size: 3.1 acres
- Days on market: 9 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,963
- Price per square foot: $186
- Lot size: 3.1 acres
- Days on market: 9 days
- View listing on realtor.com
#27. Redbud Rd Lot 7, Winchester
- Price: $749,900
- 3 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 2,368
- Price per square foot: $316
- Lot size: 4.2 acres
- Days on market: 215 days
- View listing on realtor.com
- 3 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 2,368
- Price per square foot: $316
- Lot size: 4.2 acres
- Days on market: 215 days
- View listing on realtor.com
#26. 442 Frog Hollow Rd, Winchester
- Price: $760,000
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,937
- Price per square foot: $258
- Lot size: 11.1 acres
- Days on market: 80 days
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,937
- Price per square foot: $258
- Lot size: 11.1 acres
- Days on market: 80 days
- View listing on realtor.com
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#25. 1049 Laurel Grove Rd, Winchester
- Price: $767,900
- 3 bedrooms, 3 full bathrooms
- Square feet: 2,112
- Price per square foot: $363
- Lot size: 5.0 acres
- Days on market: 82 days
- View listing on realtor.com
- 3 bedrooms, 3 full bathrooms
- Square feet: 2,112
- Price per square foot: $363
- Lot size: 5.0 acres
- Days on market: 82 days
- View listing on realtor.com
#24. 111 Babbs Mountain Rd, Winchester
- Price: $795,600
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,102
- Price per square foot: $378
- Lot size: 1.6 acres
- Days on market: 247 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,102
- Price per square foot: $378
- Lot size: 1.6 acres
- Days on market: 247 days
- View listing on realtor.com
#23. 2411 Hunting Ridge Rd, Winchester
- Price: $799,900
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 5,040
- Price per square foot: $158
- Lot size: 5.1 acres
- Days on market: 90 days (-$25,100 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 5,040
- Price per square foot: $158
- Lot size: 5.1 acres
- Days on market: 90 days (-$25,100 price reduction since listing)
- View listing on realtor.com
#22. 162 Janes Way, Winchester
- Price: $799,999
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,461
- Price per square foot: $179
- Lot size: 5.0 acres
- Days on market: 46 days (-$15,001 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,461
- Price per square foot: $179
- Lot size: 5.0 acres
- Days on market: 46 days (-$15,001 price reduction since listing)
- View listing on realtor.com
#21. 280 Graystone Ln, Winchester
- Price: $830,000
- 5 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 4,549
- Price per square foot: $182
- Lot size: 5.0 acres
- Days on market: 61 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 4,549
- Price per square foot: $182
- Lot size: 5.0 acres
- Days on market: 61 days
- View listing on realtor.com
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#20. 430 Saddleback Ln, Winchester
- Price: $849,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,532
- Price per square foot: $240
- Lot size: 8.5 acres
- Days on market: 115 days (-$49,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,532
- Price per square foot: $240
- Lot size: 8.5 acres
- Days on market: 115 days (-$49,000 price reduction since listing)
- View listing on realtor.com
#19. 1504 Brookdale Ct, Winchester
- Price: $849,990
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,254
- Price per square foot: $161
- Lot size: 0.3 acres
- Days on market: 18 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,254
- Price per square foot: $161
- Lot size: 0.3 acres
- Days on market: 18 days
- View listing on realtor.com
#18. 1006 Armistead St, Winchester
- Price: $850,000
- 4 bedrooms, 4 full bathrooms
- Square feet: 4,417
- Price per square foot: $192
- Lot size: 0.5 acres
- Days on market: 37 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms
- Square feet: 4,417
- Price per square foot: $192
- Lot size: 0.5 acres
- Days on market: 37 days
- View listing on realtor.com
#17. 101 Abrams Pointe Blvd, Winchester
- Price: $879,999
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,280
- Price per square foot: $205
- Lot size: 0.2 acres
- Days on market: 75 days (-$20,000 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,280
- Price per square foot: $205
- Lot size: 0.2 acres
- Days on market: 75 days (-$20,000 price reduction since listing)
- View listing on realtor.com
#16. 769 Seldon Dr, Winchester
- Price: $899,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,438
- Price per square foot: $202
- Lot size: 0.4 acres
- Days on market: 164 days (-$51,000 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,438
- Price per square foot: $202
- Lot size: 0.4 acres
- Days on market: 164 days (-$51,000 price reduction since listing)
- View listing on realtor.com
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#15. 229 Soldiers Rest Ln, Winchester
- Price: $925,000
- 6 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,725
- Price per square foot: $248
- Lot size: 5.0 acres
- Days on market: 1 day
- View listing on realtor.com
- 6 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,725
- Price per square foot: $248
- Lot size: 5.0 acres
- Days on market: 1 day
- View listing on realtor.com
#14. 113 Shockey Cir, Winchester
- Price: $939,000
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,363
- Price per square foot: $279
- Lot size: 0.6 acres
- Days on market: 289 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,363
- Price per square foot: $279
- Lot size: 0.6 acres
- Days on market: 289 days
- View listing on realtor.com
#13. 150 Ewell Dr, Winchester
- Price: $960,000
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,256
- Price per square foot: $153
- Lot size: 2.7 acres
- Days on market: 97 days (-$20,000 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,256
- Price per square foot: $153
- Lot size: 2.7 acres
- Days on market: 97 days (-$20,000 price reduction since listing)
- View listing on realtor.com
#12. 1020 Breckinridge Ln, Winchester
- Price: $999,000
- 6 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,540
- Price per square foot: $152
- Lot size: 0.5 acres
- Days on market: 184 days (-$100,000 price reduction since listing)
- View listing on realtor.com
- 6 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,540
- Price per square foot: $152
- Lot size: 0.5 acres
- Days on market: 184 days (-$100,000 price reduction since listing)
- View listing on realtor.com
#11. Cedar Grv Lot 52, Winchester
- Price: $999,999
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,100
- Price per square foot: $322
- Lot size: 7.7 acres
- Days on market: 117 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,100
- Price per square foot: $322
- Lot size: 7.7 acres
- Days on market: 117 days
- View listing on realtor.com
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#10. Light Rd, Winchester
- Price: $1,012,000
- 4 bedrooms, 3 full bathrooms
- Square feet: 2,211
- Price per square foot: $457
- Lot size: 15.0 acres
- Days on market: 102 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms
- Square feet: 2,211
- Price per square foot: $457
- Lot size: 15.0 acres
- Days on market: 102 days
- View listing on realtor.com
#9. Gravenstein Ct Lot 60, Winchester
- Price: $1,045,000
- 3 bedrooms, 3 full bathrooms
- Square feet: 2,875
- Price per square foot: $363
- Lot size: 2.4 acres
- Days on market: 260 days (-$75,000 price reduction since listing)
- View listing on realtor.com
- 3 bedrooms, 3 full bathrooms
- Square feet: 2,875
- Price per square foot: $363
- Lot size: 2.4 acres
- Days on market: 260 days (-$75,000 price reduction since listing)
- View listing on realtor.com
#8. Gravenstein Ct Lot 62, Winchester
- Price: $1,095,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,707
- Price per square foot: $295
- Lot size: 2.4 acres
- Days on market: 224 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,707
- Price per square foot: $295
- Lot size: 2.4 acres
- Days on market: 224 days
- View listing on realtor.com
#7. 207 W View Dr, Winchester
- Price: $1,115,000
- 7 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,180
- Price per square foot: $266
- Lot size: 6.6 acres
- Days on market: 17 days
- View listing on realtor.com
- 7 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,180
- Price per square foot: $266
- Lot size: 6.6 acres
- Days on market: 17 days
- View listing on realtor.com
#6. 410 Valley View Dr, Winchester
- Price: $1,129,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,426
- Price per square foot: $208
- Lot size: 9.8 acres
- Days on market: 138 days (-$19,000 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,426
- Price per square foot: $208
- Lot size: 9.8 acres
- Days on market: 138 days (-$19,000 price reduction since listing)
- View listing on realtor.com
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#5. 2321 Cedar Grove Rd, Winchester
- Price: $1,175,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,815
- Price per square foot: $244
- Lot size: 21.0 acres
- Days on market: 87 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,815
- Price per square foot: $244
- Lot size: 21.0 acres
- Days on market: 87 days
- View listing on realtor.com
#4. 107 Lacosta Ct, Winchester
- Price: $1,175,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,888
- Price per square foot: $302
- Lot size: 2.2 acres
- Days on market: 53 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,888
- Price per square foot: $302
- Lot size: 2.2 acres
- Days on market: 53 days
- View listing on realtor.com
#3. Honeycrisp Way Lot 18, Winchester
- Price: $1,485,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,484
- Price per square foot: $426
- Lot size: 5.0 acres
- Days on market: 18 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,484
- Price per square foot: $426
- Lot size: 5.0 acres
- Days on market: 18 days
- View listing on realtor.com
#2. 821 Apple Pie Ridge Rd, Winchester
- Price: $1,999,999
- 5 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 5,590
- Price per square foot: $357
- Lot size: 14.5 acres
- Days on market: 71 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 5,590
- Price per square foot: $357
- Lot size: 14.5 acres
- Days on market: 71 days
- View listing on realtor.com
#1. 1631 Back Mountain Rd, Winchester
- Price: $2,125,000
- 5 bedrooms, 2 full bathrooms, 2 half bathrooms
- Square feet: 4,166
- Price per square foot: $510
- Lot size: 180.1 acres
- Days on market: 46 days
- View listing on realtor.com
- 5 bedrooms, 2 full bathrooms, 2 half bathrooms
- Square feet: 4,166
- Price per square foot: $510
- Lot size: 180.1 acres
- Days on market: 46 days
- View listing on realtor.com
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