Most Expensive Homes for Sale in Winchester

#30. 601 Fall Run Ln, Winchester

- Price: $819,990
- 3 bedrooms, 2 full bathrooms
- Square feet: 2,175
- Price per square foot: $377
- Lot size: 20.1 acres
- Days on market: 38 days (-$50,010 price reduction since listing)
- 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: 289 days
- View listing on realtor.com

#28. 650 Gough Rd, Winchester

- Price: $858,375
- 3 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,469
- Price per square foot: $192
- Lot size: 2.7 acres
- Days on market: 22 days
- View listing on realtor.com

#27. 1504 Brookdale Ct, Winchester

- Price: $860,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,254
- Price per square foot: $163
- Lot size: 0.3 acres
- Days on market: 79 days (-$15,000 price reduction since listing)
- View listing on realtor.com

#26. 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: 53 days
- View listing on realtor.com

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#25. 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: 354 days
- View listing on realtor.com

#24. 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: 98 days
- View listing on realtor.com

#23. 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: 289 days
- View listing on realtor.com

#22. 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: 100 days
- View listing on realtor.com

#21. 254 Whistlewood Ln, Winchester

- Price: $915,000
- 5 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 4,301
- Price per square foot: $212
- Lot size: 5.0 acres
- Days on market: 38 days (-$24,950 price reduction since listing)
- View listing on realtor.com

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#20. 430 Saddleback Ln, Winchester

- Price: $915,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,532
- Price per square foot: $259
- Lot size: 8.5 acres
- Days on market: 17 days
- View listing on realtor.com

#19. 1509 Stone House Ct, Winchester

- Price: $925,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,566
- Price per square foot: $140
- Lot size: 0.3 acres
- Days on market: 52 days (-$34,000 price reduction since listing)
- 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: 180 days
- View listing on realtor.com

#17. 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: 8 days
- View listing on realtor.com

#16. 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: 191 days
- View listing on realtor.com

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#15. 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: 66 days
- View listing on realtor.com

#14. 247 McGuire Rd, Winchester

- Price: $950,000
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,859
- Price per square foot: $332
- Lot size: 2.7 acres
- Days on market: 53 days (-$45,000 price reduction since listing)
- View listing on realtor.com

#13. 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: 19 days
- View listing on realtor.com

#12. 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: 4 days
- View listing on realtor.com

#11. 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: 162 days (-$75,000 price reduction since listing)
- View listing on realtor.com

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#10. 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: 155 days (-$40,100 price reduction since listing)
- View listing on realtor.com

#9. 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: 126 days
- View listing on realtor.com

#8. 1020 Breckinridge Ln, Winchester

- Price: $1,099,000
- 6 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,174
- Price per square foot: $178
- Lot size: 0.5 acres
- Days on market: 86 days (-$30,000 price reduction since listing)
- 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: 146 days (-$174,000 price reduction since listing)
- View listing on realtor.com

#6. 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: 65 days
- View listing on realtor.com

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#5. 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: 40 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: 86 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: 18 days
- View listing on realtor.com

#2. 325 Windsor Ln, Winchester

- Price: $1,300,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,117
- Price per square foot: $254
- Lot size: 5.4 acres
- Days on market: 33 days
- View listing on realtor.com

#1. 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: 13 days (-$255,000 price reduction since listing)
- View listing on realtor.com

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Most expensive homes for sale in Winchester