Most Expensive Homes for Sale in Winchester

#30. 127 Triangle Ct, Winchester

- Price: $799,900
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,500
- Price per square foot: $177
- Lot size: 0.3 acres
- Days on market: 9 days
- View listing on realtor.com

#29. 279 Fishel Rd, Winchester

- Price: $799,900
- 5 bedrooms, 3 full bathrooms
- Square feet: 3,056
- Price per square foot: $261
- Lot size: 2.1 acres
- Days on market: 29 days
- View listing on realtor.com

#28. 147 Simmons Ridge Ln, Winchester

- Price: $799,900
- 5 bedrooms, 3 full bathrooms
- Square feet: 2,800
- Price per square foot: $285
- Lot size: 5.1 acres
- Days on market: 410 days
- View listing on realtor.com

#27. 5A Gough Rd, Winchester

- Price: $799,900
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,700
- Price per square foot: $296
- Lot size: 5.0 acres
- Days on market: 66 days
- View listing on realtor.com

#26. 283 Fishel Rd, Winchester

- Price: $799,900
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,700
- Price per square foot: $296
- Lot size: 2.1 acres
- Days on market: 198 days
- View listing on realtor.com

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#25. Trojan Ln Lot 14, Winchester

- Price: $802,000
- 4 bedrooms, 3 full bathrooms
- Square feet: 2,211
- Price per square foot: $362
- Lot size: 7.1 acres
- Days on market: 207 days
- View listing on realtor.com

#24. Redbud Rd Lot 6, Winchester

- Price: $818,400
- 4 bedrooms, 4 full bathrooms
- Square feet: 2,368
- Price per square foot: $345
- Lot size: 2.6 acres
- Days on market: 13 days
- View listing on realtor.com

#23. 105 Sundial Ct, Winchester

- Price: $825,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,464
- Price per square foot: $184
- Lot size: 0.3 acres
- Days on market: 20 days
- View listing on realtor.com

#22. 935 Breckinridge Ln, Winchester

- Price: $835,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,342
- Price per square foot: $192
- Lot size: 0.7 acres
- Days on market: 212 days (-$15,000 price reduction since listing)
- View listing on realtor.com

#21. 113 Forest Ridge Rd, Winchester

- Price: $839,900
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,988
- Price per square foot: $210
- Lot size: 1.3 acres
- Days on market: 88 days (-$20,000 price reduction since listing)
- View listing on realtor.com

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#20. 840 Carpers Valley Rd, Winchester

- Price: $875,000
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,888
- Price per square foot: $225
- Lot size: 5.9 acres
- Days on market: 2 days
- View listing on realtor.com

#19. 115 Winterberry Ct, Winchester

- Price: $879,900
- 6 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 9,608
- Price per square foot: $91
- Lot size: 0.5 acres
- Days on market: 136 days (-$19,100 price reduction since listing)
- View listing on realtor.com

#18. 100 Abrams Pointe Blvd, Winchester

- Price: $879,999
- 4 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 4,230
- Price per square foot: $208
- Lot size: 0.3 acres
- Days on market: 18 days
- View listing on realtor.com

#17. 281 Fishel Rd, Winchester

- Price: $899,900
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,100
- Price per square foot: $290
- Lot size: 3.1 acres
- Days on market: 395 days
- View listing on realtor.com

#16. 210 McGuire Rd, Winchester

- Price: $960,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,524
- Price per square foot: $212
- Lot size: 3.1 acres
- Days on market: 62 days
- View listing on realtor.com

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#15. 154 Windsor Ln, Winchester

- Price: $979,000
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,412
- Price per square foot: $286
- Lot size: 5.0 acres
- Days on market: 38 days
- View listing on realtor.com

#14. 1321 Vanceright Cir, Winchester

- Price: $995,000
- 3 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,793
- Price per square foot: $262
- Lot size: 0.7 acres
- Days on market: 107 days (-$105,000 price reduction since listing)
- View listing on realtor.com

#13. 874 Carpers Valley Rd, Winchester

- Price: $999,900
- 4 bedrooms, 2 full bathrooms
- Square feet: 3,216
- Price per square foot: $310
- Lot size: 45.3 acres
- Days on market: 2 days
- View listing on realtor.com

#12. 939 Buckner Dr, Winchester

- Price: $1,070,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,122
- Price per square foot: $174
- Lot size: 0.4 acres
- Days on market: 61 days (-$30,000 price reduction since listing)
- View listing on realtor.com

#11. 1004 Heth Pl, Winchester

- Price: $1,249,000
- 4 bedrooms, 3 full bathrooms, 2 half bathrooms
- Square feet: 5,184
- Price per square foot: $240
- Lot size: 0.4 acres
- Days on market: 156 days
- View listing on realtor.com

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#10. 3372 Hunting Ridge Rd, Winchester

- Price: $1,298,500
- 4 bedrooms, 3 full bathrooms
- Square feet: 2,344
- Price per square foot: $553
- Lot size: 6.6 acres
- Days on market: 375 days (-$143,500 price reduction since listing)
- View listing on realtor.com

#9. 255 White Rd, Winchester

- Price: $1,349,000
- 6 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,900
- Price per square foot: $228
- Lot size: 30.5 acres
- Days on market: 187 days (-$40,000 price reduction since listing)
- View listing on realtor.com

#8. 1960 Great Mountain Ln, Winchester

- Price: $1,350,000
- 3 bedrooms, 3 full bathrooms
- Square feet: 2,434
- Price per square foot: $554
- Lot size: 96.4 acres
- Days on market: 11 days
- View listing on realtor.com

#7. 1460 Pitcock Ln, Winchester

- Price: $1,399,999
- 4 bedrooms, 4 full bathrooms
- Square feet: 4,949
- Price per square foot: $282
- Lot size: 27.6 acres
- Days on market: 137 days
- View listing on realtor.com

#6. 510 N Loudoun St, Winchester

- Price: $1,499,000
- 12 bedrooms, 9 full bathrooms
- Square feet: 7,788
- Price per square foot: $192
- Lot size: 0.3 acres
- Days on market: 32 days
- View listing on realtor.com

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#5. 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: 180 days
- View listing on realtor.com

#4. 407 S Washington St, Winchester

- Price: $1,599,999
- 6 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 5,814
- Price per square foot: $275
- Lot size: 1.0 acres
- Days on market: 10 days
- View listing on realtor.com

#3. 202 S Washington St, Winchester

- Price: $1,600,000
- 7 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 8,616
- Price per square foot: $185
- Lot size: 0.3 acres
- Days on market: 73 days
- View listing on realtor.com

#2. 210 Rubinette Way, Winchester

- Price: $1,850,000
- 4 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 7,773
- Price per square foot: $238
- Lot size: 42.4 acres
- Days on market: 110 days (-$149,990 price reduction since listing)
- View listing on realtor.com

#1. 2361 Indian Hollow Rd, Winchester

- Price: $2,500,000
- 4 bedrooms, 4 full bathrooms
- Square feet: 4,297
- Price per square foot: $581
- Lot size: 93.0 acres
- Days on market: 229 days (-$1,000,000 price reduction since listing)
- View listing on realtor.com

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Most expensive homes for sale in Winchester