Most expensive homes for sale in Winchester
Written by:
September 29, 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. 756 Brookneil Dr, Winchester
- Price: $815,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,942
- Price per square foot: $206
- Lot size: 9.0 acres
- Days on market: 96 days (-$34,990 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,942
- Price per square foot: $206
- Lot size: 9.0 acres
- Days on market: 96 days (-$34,990 price reduction since listing)
- View listing on realtor.com
#29. 700 S Stewart St, Winchester
- Price: $819,900
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,063
- Price per square foot: $267
- Lot size: 0.2 acres
- Days on market: 37 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,063
- Price per square foot: $267
- Lot size: 0.2 acres
- Days on market: 37 days
- View listing on realtor.com
#28. 601 Fall Run Ln, Winchester
- Price: $819,950
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,175
- Price per square foot: $376
- Lot size: 20.1 acres
- Days on market: 80 days (-$40 price reduction since listing)
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,175
- Price per square foot: $376
- Lot size: 20.1 acres
- Days on market: 80 days (-$40 price reduction since listing)
- View listing on realtor.com
#27. Oak Dr Lot 7, Winchester
- Price: $829,900
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,700
- Price per square foot: $307
- Lot size: 5.0 acres
- Days on market: 331 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,700
- Price per square foot: $307
- Lot size: 5.0 acres
- Days on market: 331 days
- View listing on realtor.com
#26. 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: 5 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: 5 days
- View listing on realtor.com
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#25. 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: 121 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: 121 days (-$10,010 price reduction since listing)
- View listing on realtor.com
#24. 1517 Brookdale Ct, Winchester
- Price: $869,500
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,368
- Price per square foot: $136
- Lot size: 0.4 acres
- Days on market: 95 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,368
- Price per square foot: $136
- Lot size: 0.4 acres
- Days on market: 95 days
- View listing on realtor.com
#23. 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: 80 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: 80 days (-$9,000 price reduction since listing)
- View listing on realtor.com
#22. 430 Saddleback Ln, Winchester
- Price: $898,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,532
- Price per square foot: $254
- Lot size: 8.5 acres
- Days on market: 59 days (-$17,000 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: $254
- Lot size: 8.5 acres
- Days on market: 59 days (-$17,000 price reduction since listing)
- View listing on realtor.com
#21. 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: 396 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: 396 days
- View listing on realtor.com
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#20. 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: 108 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: 108 days (-$51,000 price reduction since listing)
- View listing on realtor.com
#19. Fishel Rd Lot 1B, Winchester
- Price: $899,900
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,100
- Price per square foot: $290
- Lot size: 5.0 acres
- Days on market: 331 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,100
- Price per square foot: $290
- Lot size: 5.0 acres
- Days on market: 331 days
- View listing on realtor.com
#18. 101 Abrams Pointe Blvd, Winchester
- Price: $899,999
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,280
- Price per square foot: $210
- Lot size: 0.2 acres
- Days on market: 19 days
- View listing on realtor.com
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,280
- Price per square foot: $210
- Lot size: 0.2 acres
- Days on market: 19 days
- View listing on realtor.com
#17. 1A Fishel Rd, 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: 222 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: 222 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: 50 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: 50 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: 233 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: 233 days
- View listing on realtor.com
#14. 150 Ewell Dr, Winchester
- Price: $980,000
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,256
- Price per square foot: $156
- Lot size: 2.7 acres
- Days on market: 41 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,256
- Price per square foot: $156
- Lot size: 2.7 acres
- Days on market: 41 days
- View listing on realtor.com
#13. 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: 128 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: 128 days (-$100,000 price reduction since listing)
- View listing on realtor.com
#12. 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: 61 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: 61 days
- View listing on realtor.com
#11. 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: 46 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: 46 days
- View listing on realtor.com
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#10. 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: 204 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: 204 days (-$75,000 price reduction since listing)
- View listing on realtor.com
#9. 700 Miller Rd, Winchester
- Price: $1,074,900
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 5,058
- Price per square foot: $212
- Lot size: 2.5 acres
- Days on market: 197 days (-$40,100 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 5,058
- Price per square foot: $212
- Lot size: 2.5 acres
- Days on market: 197 days (-$40,100 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: 188 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: 188 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: 168 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: 168 days
- View listing on realtor.com
#6. 410 Valley View Dr, Winchester
- Price: $1,148,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,426
- Price per square foot: $211
- Lot size: 9.8 acres
- Days on market: 82 days (-$22,000 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: $211
- Lot size: 9.8 acres
- Days on market: 82 days (-$22,000 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: 107 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: 107 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: 31 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: 31 days
- View listing on realtor.com
#3. 291 Lake Serene Dr, Winchester
- Price: $1,299,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,994
- Price per square foot: $260
- Lot size: 1.3 acres
- Days on market: 60 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,994
- Price per square foot: $260
- Lot size: 1.3 acres
- Days on market: 60 days
- View listing on realtor.com
#2. 731 Apple Pie Ridge Rd, Winchester
- Price: $1,495,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,304
- Price per square foot: $347
- Lot size: 11.4 acres
- Days on market: 55 days (-$255,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,304
- Price per square foot: $347
- Lot size: 11.4 acres
- Days on market: 55 days (-$255,000 price reduction since listing)
- View listing on realtor.com
#1. 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: 15 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: 15 days
- View listing on realtor.com
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