Most expensive homes for sale in Winchester
Written by:
November 3, 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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#30. 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: 54 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: 54 days
- View listing on realtor.com
#29. 127 Triangle Ct, Winchester
- Price: $789,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,500
- Price per square foot: $225
- Lot size: 0.3 acres
- Days on market: 222 days (-$5,500 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,500
- Price per square foot: $225
- Lot size: 0.3 acres
- Days on market: 222 days (-$5,500 price reduction since listing)
- View listing on realtor.com
#28. 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: 219 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: 219 days
- View listing on realtor.com
#27. 109 Jeni Ct, Winchester
- Price: $799,000
- 6 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,000
- Price per square foot: $199
- Lot size: 0.3 acres
- Days on market: 69 days
- View listing on realtor.com
- 6 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,000
- Price per square foot: $199
- Lot size: 0.3 acres
- Days on market: 69 days
- View listing on realtor.com
#26. 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: 62 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: 62 days (-$25,100 price reduction since listing)
- View listing on realtor.com
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#25. 162 Janes Way, Winchester
- Price: $815,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,461
- Price per square foot: $182
- Lot size: 5.0 acres
- Days on market: 18 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,461
- Price per square foot: $182
- Lot size: 5.0 acres
- Days on market: 18 days
- View listing on realtor.com
#24. 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: 33 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: 33 days
- View listing on realtor.com
#23. 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: 149 days (-$10,010 price reduction since listing)
- 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: 149 days (-$10,010 price reduction since listing)
- View listing on realtor.com
#22. 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: 9 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: 9 days
- View listing on realtor.com
#21. 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: 47 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: 47 days (-$20,000 price reduction since listing)
- View listing on realtor.com
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#20. 254 Whistlewood Ln, Winchester
- Price: $890,000
- 5 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 4,301
- Price per square foot: $206
- Lot size: 5.0 acres
- Days on market: 108 days (-$9,000 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 4,301
- Price per square foot: $206
- Lot size: 5.0 acres
- Days on market: 108 days (-$9,000 price reduction since listing)
- View listing on realtor.com
#19. 219 Taggart Dr, Winchester
- Price: $898,400
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,675
- Price per square foot: $244
- Lot size: 0.3 acres
- Days on market: 424 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,675
- Price per square foot: $244
- Lot size: 0.3 acres
- Days on market: 424 days
- View listing on realtor.com
#18. 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: 136 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: 136 days (-$51,000 price reduction since listing)
- View listing on realtor.com
#17. 125 Split Ridge Ln, Winchester
- Price: $929,900
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,100
- Price per square foot: $299
- Lot size: 5.0 acres
- Days on market: 250 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,100
- Price per square foot: $299
- Lot size: 5.0 acres
- Days on market: 250 days
- View listing on realtor.com
#16. 3328 Millwood Pike, Winchester
- Price: $935,000
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,624
- Price per square foot: $356
- Lot size: 20.5 acres
- Days on market: 78 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,624
- Price per square foot: $356
- Lot size: 20.5 acres
- Days on market: 78 days
- View listing on realtor.com
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#15. 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: 261 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: 261 days
- View listing on realtor.com
#14. 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: 69 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: 69 days (-$20,000 price reduction since listing)
- View listing on realtor.com
#13. 206 Covey Ln, Winchester
- Price: $968,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,879
- Price per square foot: $198
- Lot size: 2.7 acres
- Days on market: 9 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,879
- Price per square foot: $198
- Lot size: 2.7 acres
- Days on market: 9 days
- 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: 156 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: 156 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: 89 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: 89 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: 74 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: 74 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: 232 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: 232 days (-$75,000 price reduction since listing)
- View listing on realtor.com
#8. 1460 Pitcock Ln, Winchester
- Price: $1,095,000
- 4 bedrooms, 4 full bathrooms
- Square feet: 4,949
- Price per square foot: $221
- Lot size: 27.6 acres
- Days on market: 216 days (-$30,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms
- Square feet: 4,949
- Price per square foot: $221
- Lot size: 27.6 acres
- Days on market: 216 days (-$30,000 price reduction since listing)
- View listing on realtor.com
#7. 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: 196 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: 196 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: 110 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: 110 days (-$19,000 price reduction since listing)
- View listing on realtor.com
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#5. 207 Westview Dr, Winchester
- Price: $1,149,000
- 7 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,380
- Price per square foot: $180
- Lot size: 6.6 acres
- Days on market: 135 days (-$46,000 price reduction since listing)
- View listing on realtor.com
- 7 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,380
- Price per square foot: $180
- Lot size: 6.6 acres
- Days on market: 135 days (-$46,000 price reduction since listing)
- View listing on realtor.com
#4. 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: 59 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: 59 days
- View listing on realtor.com
#3. 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: 25 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: 25 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: 43 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: 43 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: 18 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: 18 days
- View listing on realtor.com
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