Most expensive homes for sale in Winchester
Written by:
July 28, 2025
Volodymyr Kyrylyuk // Shutterstock
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. 251 Heather Hill Ln, Winchester
- Price: $849,900
- 3 bedrooms, 2 full bathrooms
- Square feet: 1,456
- Price per square foot: $583
- Lot size: 48.8 acres
- Days on market: 93 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 1,456
- Price per square foot: $583
- Lot size: 48.8 acres
- Days on market: 93 days
- View listing on realtor.com
#29. 756 Brookneil Dr, Winchester
- Price: $849,990
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,942
- Price per square foot: $215
- Lot size: 9.0 acres
- Days on market: 19 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,942
- Price per square foot: $215
- Lot size: 9.0 acres
- Days on market: 19 days
- View listing on realtor.com
#28. 939 Buckner Dr, Winchester
- Price: $850,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,122
- Price per square foot: $138
- Lot size: 0.4 acres
- Days on market: 18 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,122
- Price per square foot: $138
- Lot size: 0.4 acres
- Days on market: 18 days
- View listing on realtor.com
#27. 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: 18 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: 18 days
- View listing on realtor.com
#26. 601 Fall Run Ln, Winchester
- Price: $870,000
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,175
- Price per square foot: $400
- Lot size: 20.1 acres
- Days on market: 3 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,175
- Price per square foot: $400
- Lot size: 20.1 acres
- Days on market: 3 days
- View listing on realtor.com
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#25. 1504 Brookdale Ct, Winchester
- Price: $875,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,254
- Price per square foot: $166
- Lot size: 0.3 acres
- Days on market: 44 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,254
- Price per square foot: $166
- Lot size: 0.3 acres
- Days on market: 44 days
- View listing on realtor.com
#24. 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: 319 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: 319 days
- View listing on realtor.com
#23. 442 Frog Hollow Rd, Winchester
- Price: $899,000
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,937
- Price per square foot: $306
- Lot size: 16.1 acres
- Days on market: 63 days
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,937
- Price per square foot: $306
- Lot size: 16.1 acres
- Days on market: 63 days
- View listing on realtor.com
#22. 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: 254 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: 254 days
- View listing on realtor.com
#21. 196 Hodges Ln, Winchester
- Price: $910,000
- 2 bedrooms, 1 full bathrooms
- Square feet: 609
- Price per square foot: $1,494
- Lot size: 79.2 acres
- Days on market: 65 days
- View listing on realtor.com
- 2 bedrooms, 1 full bathrooms
- Square feet: 609
- Price per square foot: $1,494
- Lot size: 79.2 acres
- Days on market: 65 days
- View listing on realtor.com
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#20. 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: 145 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: 145 days
- View listing on realtor.com
#19. 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: 156 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: 156 days
- View listing on realtor.com
#18. 254 Whistlewood Ln, Winchester
- Price: $939,950
- 5 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 4,301
- Price per square foot: $218
- Lot size: 5.0 acres
- Days on market: 3 days
- View listing on realtor.com
- 5 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 4,301
- Price per square foot: $218
- Lot size: 5.0 acres
- Days on market: 3 days
- View listing on realtor.com
#17. 769 Seldon Dr, Winchester
- Price: $950,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,438
- Price per square foot: $214
- Lot size: 0.4 acres
- Days on market: 31 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,438
- Price per square foot: $214
- Lot size: 0.4 acres
- Days on market: 31 days
- View listing on realtor.com
#16. 1509 Stone House Ct, Winchester
- Price: $959,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,566
- Price per square foot: $146
- Lot size: 0.3 acres
- Days on market: 17 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,566
- Price per square foot: $146
- Lot size: 0.3 acres
- Days on market: 17 days
- View listing on realtor.com
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#15. 1321 Vanceright Cir, Winchester
- Price: $970,800
- 3 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,793
- Price per square foot: $255
- Lot size: 0.7 acres
- Days on market: 408 days (-$24,200 price reduction since listing)
- View listing on realtor.com
- 3 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,793
- Price per square foot: $255
- Lot size: 0.7 acres
- Days on market: 408 days (-$24,200 price reduction since listing)
- View listing on realtor.com
#14. 247 McGuire Rd, Winchester
- Price: $995,000
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,859
- Price per square foot: $348
- Lot size: 2.7 acres
- Days on market: 18 days
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,859
- Price per square foot: $348
- Lot size: 2.7 acres
- Days on market: 18 days
- View listing on realtor.com
#13. 220 Anna Margaret Dr, Winchester
- Price: $999,900
- 4 bedrooms, 3 full bathrooms, 2 half bathrooms
- Square feet: 5,000
- Price per square foot: $199
- Lot size: 2.7 acres
- Days on market: 64 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 2 half bathrooms
- Square feet: 5,000
- Price per square foot: $199
- Lot size: 2.7 acres
- Days on market: 64 days
- View listing on realtor.com
#12. 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: 127 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: 127 days (-$75,000 price reduction since listing)
- View listing on realtor.com
#11. 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: 120 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: 120 days (-$40,100 price reduction since listing)
- View listing on realtor.com
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#10. 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: 91 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: 91 days
- View listing on realtor.com
#9. 1460 Pitcock Ln, Winchester
- Price: $1,125,000
- 4 bedrooms, 4 full bathrooms
- Square feet: 4,949
- Price per square foot: $227
- Lot size: 27.6 acres
- Days on market: 111 days (-$174,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms
- Square feet: 4,949
- Price per square foot: $227
- Lot size: 27.6 acres
- Days on market: 111 days (-$174,000 price reduction since listing)
- View listing on realtor.com
#8. 1020 Breckinridge Ln, Winchester
- Price: $1,129,000
- 6 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,174
- Price per square foot: $182
- Lot size: 0.5 acres
- Days on market: 51 days
- View listing on realtor.com
- 6 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,174
- Price per square foot: $182
- Lot size: 0.5 acres
- Days on market: 51 days
- View listing on realtor.com
#7. 207 Westview Dr, Winchester
- Price: $1,195,000
- 7 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,380
- Price per square foot: $187
- Lot size: 6.6 acres
- Days on market: 30 days
- View listing on realtor.com
- 7 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,380
- Price per square foot: $187
- Lot size: 6.6 acres
- Days on market: 30 days
- View listing on realtor.com
#6. 410 Valley View Dr, Winchester
- Price: $1,195,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,426
- Price per square foot: $220
- Lot size: 9.8 acres
- Days on market: 5 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,426
- Price per square foot: $220
- Lot size: 9.8 acres
- Days on market: 5 days
- View listing on realtor.com
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#5. 331 N Braddock St, Winchester
- Price: $1,199,997
- 5 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 6,517
- Price per square foot: $184
- Lot size: 0.2 acres
- Days on market: 97 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 6,517
- Price per square foot: $184
- Lot size: 0.2 acres
- Days on market: 97 days
- View listing on realtor.com
#4. 801 Armistead St, Winchester
- Price: $1,224,000
- 5 bedrooms, 3 full bathrooms, 2 half bathrooms
- Square feet: 5,695
- Price per square foot: $214
- Lot size: 0.5 acres
- Days on market: 51 days
- View listing on realtor.com
- 5 bedrooms, 3 full bathrooms, 2 half bathrooms
- Square feet: 5,695
- Price per square foot: $214
- Lot size: 0.5 acres
- Days on market: 51 days
- View listing on realtor.com
#3. 374 Stonymeade Dr, Winchester
- Price: $1,299,000
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,702
- Price per square foot: $276
- Lot size: 2.8 acres
- Days on market: 23 days
- View listing on realtor.com
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,702
- Price per square foot: $276
- Lot size: 2.8 acres
- Days on market: 23 days
- View listing on realtor.com
#2. 291 Lake Serene Dr, Winchester
- Price: $1,485,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,754
- Price per square foot: $258
- Lot size: 1.3 acres
- Days on market: 137 days (-$110,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,754
- Price per square foot: $258
- Lot size: 1.3 acres
- Days on market: 137 days (-$110,000 price reduction since listing)
- View listing on realtor.com
#1. 103 Oak Ridge Ln, Winchester
- Price: $1,499,000
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 9,447
- Price per square foot: $158
- Lot size: 1.6 acres
- Days on market: 165 days (-$200,000 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 9,447
- Price per square foot: $158
- Lot size: 1.6 acres
- Days on market: 165 days (-$200,000 price reduction since listing)
- View listing on realtor.com
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