Most expensive homes for sale in Winchester
Written by:
June 9, 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. 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: 48 days (-$49,990 price reduction since listing)
- 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: 48 days (-$49,990 price reduction since listing)
- View listing on realtor.com
#29. 373 Greenfield Dr, Winchester
- Price: $850,000
- 4 bedrooms, 4 full bathrooms
- Square feet: 3,612
- Price per square foot: $235
- Lot size: 8.0 acres
- Days on market: 42 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms
- Square feet: 3,612
- Price per square foot: $235
- Lot size: 8.0 acres
- Days on market: 42 days
- View listing on realtor.com
#28. 1517 Brookdale Ct, Winchester
- Price: $869,500
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,368
- Price per square foot: $199
- Lot size: 0.4 acres
- Days on market: 28 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,368
- Price per square foot: $199
- Lot size: 0.4 acres
- Days on market: 28 days
- View listing on realtor.com
#27. 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: 2 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: 2 days
- View listing on realtor.com
#26. 103 Derrynan Ct, Winchester
- Price: $875,000
- 4 bedrooms, 3 full bathrooms
- Square feet: 2,566
- Price per square foot: $340
- Lot size: 0.3 acres
- Days on market: 9 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms
- Square feet: 2,566
- Price per square foot: $340
- Lot size: 0.3 acres
- Days on market: 9 days
- View listing on realtor.com
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#25. 111 Sundial Ct, Winchester
- Price: $880,000
- 6 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,363
- Price per square foot: $201
- Days on market: 137 days
- View listing on realtor.com
- 6 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,363
- Price per square foot: $201
- Days on market: 137 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: 277 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: 277 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: 21 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: 21 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: 212 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: 212 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: 23 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: 23 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: 103 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: 103 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: 114 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: 114 days
- View listing on realtor.com
#18. 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: 366 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: 366 days (-$24,200 price reduction since listing)
- View listing on realtor.com
#17. 241 Clayhill Dr, Winchester
- Price: $975,000
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,672
- Price per square foot: $265
- Lot size: 5.0 acres
- Days on market: 19 days
- View listing on realtor.com
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,672
- Price per square foot: $265
- Lot size: 5.0 acres
- Days on market: 19 days
- View listing on realtor.com
#16. 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: 22 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: 22 days
- View listing on realtor.com
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#15. 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: 85 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: 85 days (-$75,000 price reduction since listing)
- View listing on realtor.com
#14. 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: 49 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: 49 days
- View listing on realtor.com
#13. 700 Miller Rd, Winchester
- Price: $1,115,000
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 5,058
- Price per square foot: $220
- Lot size: 2.5 acres
- Days on market: 78 days (-$50,000 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: $220
- Lot size: 2.5 acres
- Days on market: 78 days (-$50,000 price reduction since listing)
- View listing on realtor.com
#12. 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: 69 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: 69 days (-$174,000 price reduction since listing)
- View listing on realtor.com
#11. 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: 9 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: 9 days
- View listing on realtor.com
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#10. 207 Westview Dr, Winchester
- Price: $1,199,000
- 7 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,600
- Price per square foot: $181
- Lot size: 6.6 acres
- Days on market: 166 days (-$100,000 price reduction since listing)
- View listing on realtor.com
- 7 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,600
- Price per square foot: $181
- Lot size: 6.6 acres
- Days on market: 166 days (-$100,000 price reduction since listing)
- View listing on realtor.com
#9. 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: 55 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: 55 days
- View listing on realtor.com
#8. 823 Armistead St, Winchester
- Price: $1,200,000
- 3 bedrooms, 3 full bathrooms
- Square feet: not available
- Price per square foot: not available
- Days on market: 25 days
- View listing on realtor.com
- 3 bedrooms, 3 full bathrooms
- Square feet: not available
- Price per square foot: not available
- Days on market: 25 days
- View listing on realtor.com
#7. 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: 9 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: 9 days
- View listing on realtor.com
#6. 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: 332 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: 332 days (-$140,000 price reduction since listing)
- View listing on realtor.com
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#5. 2277 Indian Hollow Rd, Winchester
- Price: $1,295,000
- 3 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 2,880
- Price per square foot: $449
- Lot size: 30.0 acres
- Days on market: 24 days
- View listing on realtor.com
- 3 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 2,880
- Price per square foot: $449
- Lot size: 30.0 acres
- Days on market: 24 days
- View listing on realtor.com
#4. 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: 95 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: 95 days (-$110,000 price reduction since listing)
- View listing on realtor.com
#3. 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: 123 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: 123 days (-$200,000 price reduction since listing)
- View listing on realtor.com
#2. 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: 439 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: 439 days
- View listing on realtor.com
#1. 908 Cedar Creek Grade, Winchester
- Price: $2,098,000
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 7,190
- Price per square foot: $291
- Lot size: 2.6 acres
- Days on market: 165 days (-$52,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 7,190
- Price per square foot: $291
- Lot size: 2.6 acres
- Days on market: 165 days (-$52,000 price reduction since listing)
- View listing on realtor.com
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