Most expensive homes for sale in Winchester
Written by:
June 30, 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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Cities with the most expensive homes in the Winchester metro area
#30. 127 Triangle Ct, Winchester
- Price: $824,999
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,500
- Price per square foot: $183
- Lot size: 0.3 acres
- Days on market: 79 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,500
- Price per square foot: $183
- Lot size: 0.3 acres
- Days on market: 79 days
- View listing on realtor.com
#29. 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: 233 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: 233 days
- View listing on realtor.com
#28. 103 Derrynan Ct, Winchester
- Price: $835,000
- 4 bedrooms, 3 full bathrooms
- Square feet: 2,731
- Price per square foot: $305
- Lot size: 0.3 acres
- Days on market: 30 days (-$40,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms
- Square feet: 2,731
- Price per square foot: $305
- Lot size: 0.3 acres
- Days on market: 30 days (-$40,000 price reduction since listing)
- View listing on realtor.com
#27. 373 Greenfield Dr, Winchester
- Price: $839,000
- 4 bedrooms, 4 full bathrooms
- Square feet: 3,612
- Price per square foot: $232
- Lot size: 8.0 acres
- Days on market: 63 days (-$11,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms
- Square feet: 3,612
- Price per square foot: $232
- Lot size: 8.0 acres
- Days on market: 63 days (-$11,000 price reduction since listing)
- View listing on realtor.com
#26. 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: 72 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: 72 days
- View listing on realtor.com
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#25. 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: 49 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: 49 days
- View listing on realtor.com
#24. 1504 Brookdale Ct, Winchester
- Price: $875,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,254
- Price per square foot: $166
- Lot size: 0.3 acres
- Days on market: 23 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,254
- Price per square foot: $166
- Lot size: 0.3 acres
- Days on market: 23 days
- View listing on realtor.com
#23. 132 Wilton Dr, Winchester
- Price: $879,000
- 5 bedrooms, 2 full bathrooms, 2 half bathrooms
- Square feet: 5,161
- Price per square foot: $170
- Lot size: 2.6 acres
- Days on market: 4 days
- View listing on realtor.com
- 5 bedrooms, 2 full bathrooms, 2 half bathrooms
- Square feet: 5,161
- Price per square foot: $170
- Lot size: 2.6 acres
- Days on market: 4 days
- View listing on realtor.com
#22. 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: 298 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: 298 days
- View listing on realtor.com
#21. 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: 42 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: 42 days
- View listing on realtor.com
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#20. 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: 233 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: 233 days
- View listing on realtor.com
#19. 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: 44 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: 44 days
- View listing on realtor.com
#18. 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: 124 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: 124 days
- View listing on realtor.com
#17. 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: 135 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: 135 days
- View listing on realtor.com
#16. 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: 10 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: 10 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: 387 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: 387 days (-$24,200 price reduction since listing)
- View listing on realtor.com
#14. 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: 43 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: 43 days
- View listing on realtor.com
#13. Gravenstein Ct Lot 60, Winchester
- Price: $1,045,000
- 3 bedrooms, 3 full bathrooms
- Square feet: 2,750
- Price per square foot: $380
- Lot size: 2.4 acres
- Days on market: 106 days (-$75,000 price reduction since listing)
- View listing on realtor.com
- 3 bedrooms, 3 full bathrooms
- Square feet: 2,750
- Price per square foot: $380
- Lot size: 2.4 acres
- Days on market: 106 days (-$75,000 price reduction since listing)
- View listing on realtor.com
#12. 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: 99 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: 99 days (-$40,100 price reduction since listing)
- View listing on realtor.com
#11. 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: 70 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: 70 days
- View listing on realtor.com
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#10. 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: 90 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: 90 days (-$174,000 price reduction since listing)
- View listing on realtor.com
#9. 1020 Breckinridge Ln, Winchester
- Price: $1,129,000
- 8 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,174
- Price per square foot: $182
- Lot size: 0.5 acres
- Days on market: 30 days
- View listing on realtor.com
- 8 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,174
- Price per square foot: $182
- Lot size: 0.5 acres
- Days on market: 30 days
- View listing on realtor.com
#8. 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: 9 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: 9 days
- View listing on realtor.com
#7. 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: 76 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: 76 days
- View listing on realtor.com
#6. 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: 30 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: 30 days
- View listing on realtor.com
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#5. 202 S Washington St, Winchester
- Price: $1,250,000
- 7 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 8,616
- Price per square foot: $145
- Lot size: 0.3 acres
- Days on market: 353 days (-$140,000 price reduction since listing)
- View listing on realtor.com
- 7 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 8,616
- Price per square foot: $145
- Lot size: 0.3 acres
- Days on market: 353 days (-$140,000 price reduction since listing)
- View listing on realtor.com
#4. 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: 2 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: 2 days
- View listing on realtor.com
#3. 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: 116 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: 116 days (-$110,000 price reduction since listing)
- View listing on realtor.com
#2. 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: 144 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: 144 days (-$200,000 price reduction since listing)
- View listing on realtor.com
#1. 821, Winchester
- Price: $1,500,000
- 3 bedrooms, 2 full bathrooms
- Square feet: not available
- Price per square foot: not available
- Lot size: 2.5 acres
- Days on market: 460 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms
- Square feet: not available
- Price per square foot: not available
- Lot size: 2.5 acres
- Days on market: 460 days
- View listing on realtor.com
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