Most Expensive Homes for Sale in Winchester

#30. 400 Great Mountain Ln, Winchester

- Price: $799,000
- 2 bedrooms, 2 full bathrooms
- Square feet: 1,600
- Price per square foot: $499
- Lot size: 99.8 acres
- Days on market: 108 days (-$26,000 price reduction since listing)
- View listing on realtor.com

#29. 977 W Parkins Mill Rd, Winchester

- Price: $799,900
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,928
- Price per square foot: $203
- Lot size: 5.1 acres
- Days on market: 31 days
- View listing on realtor.com

#28. 181 Oak Dr, Winchester

- Price: $799,900
- 5 bedrooms, 3 full bathrooms
- Square feet: 3,056
- Price per square foot: $261
- Lot size: 5.0 acres
- Days on market: 262 days
- View listing on realtor.com

#27. 103 Derrynan Ct, Winchester

- Price: $799,900
- 4 bedrooms, 3 full bathrooms
- Square feet: 2,731
- Price per square foot: $292
- Lot size: 0.3 acres
- Days on market: 37 days (-$35,100 price reduction since listing)
- View listing on realtor.com

#26. 230 Tranquil Wood Ln, Winchester

- Price: $810,127
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,046
- Price per square foot: $395
- Lot size: 3.1 acres
- Days on market: 258 days (-$9,000 price reduction since listing)
- View listing on realtor.com

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#25. 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: 86 days
- View listing on realtor.com

#24. 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: 240 days
- View listing on realtor.com

#23. 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: 79 days
- View listing on realtor.com

#22. 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: 5 days
- View listing on realtor.com

#21. 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: 4 days
- View listing on realtor.com

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#20. 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: 4 days
- View listing on realtor.com

#19. 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: 30 days
- View listing on realtor.com

#18. 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: 11 days
- View listing on realtor.com

#17. 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: 305 days
- View listing on realtor.com

#16. 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: 49 days
- View listing on realtor.com

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#15. 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: 51 days
- View listing on realtor.com

#14. 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: 142 days
- View listing on realtor.com

#13. 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: 17 days
- View listing on realtor.com

#12. 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: 3 days
- View listing on realtor.com

#11. 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: 394 days (-$24,200 price reduction since listing)
- 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: 113 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: 106 days (-$40,100 price reduction since listing)
- View listing on realtor.com

#8. 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: 77 days
- View listing on realtor.com

#7. 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: 97 days (-$174,000 price reduction since listing)
- View listing on realtor.com

#6. 1020 Breckinridge Ln, Winchester

- Price: $1,129,000
- 7 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,174
- Price per square foot: $182
- Lot size: 0.5 acres
- Days on market: 37 days
- View listing on realtor.com

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#5. 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: 16 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: 37 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: 9 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: 123 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: 151 days (-$200,000 price reduction since listing)
- View listing on realtor.com

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Most expensive homes for sale in Winchester